1646:
plants that have been investigated. It is present in all the different parts of plants, including leaves, stems, roots, fruits, and seeds, in varying proportions. Melatonin concentrations differ not only among plant species, but also between varieties of the same species depending on the agronomic growing conditions, varying from picograms to several micrograms per gram. Notably high melatonin concentrations have been measured in popular beverages such as coffee, tea, wine, and beer, and crops including corn, rice, wheat, barley, and oats. In some common foods and beverages, including coffee and walnuts, the concentration of melatonin has been estimated or measured to be sufficiently high to raise the blood level of melatonin above daytime baseline values.
365:
238:
65:
1071:
881:
722:
1672:. Studies conducted on lettuce grown in saline soil conditions have shown that the application of melatonin significantly mitigates the harmful effects of salinity. Foliar application increases the number of leaves, their surface area, increases fresh weight and the content of chlorophyll a and chlorophyll b, and the content of carotenoids compared to plants not treated with melatonin.
1650:
membrane-bound receptors analogous to those known in animals have been described. Rather, melatonin performs important roles in plants as a growth regulator, as well as environmental stress protector. It is synthesized in plants when they are exposed to both biological stresses, for example, fungal infection, and nonbiological stresses such as extremes of temperature, toxins, increased
56:
8841:
4604:
802:, emphasizing its role not only in direct free radical scavenging but also in modulating the expression of antioxidant enzymes and maintaining mitochondrial integrity. This multifaceted role shows the physiological significance of melatonin as a mitochondrial antioxidant, a notion supported by numerous scholars.
1442:
Melatonin's discovery is linked to the study of skin color changes in some amphibians and reptiles, a phenomenon initially observed through the administration of pineal gland extracts. In 1917, Carey Pratt McCord and Floyd P. Allen found that feeding extracts from the pineal glands of cows caused the
1566:
Many animals and humans use the variation in duration of melatonin production each day as a seasonal clock. In animals including humans, the profile of melatonin synthesis and secretion is affected by the variable duration of night in summer as compared to winter. The change in duration of secretion
5126:
Exogenous melatonin has acute sleepiness-inducing and temperature-lowering effects during 'biological daytime', and when suitably timed (it is most effective around dusk and dawn), it will shift the phase of the human circadian clock (sleep, endogenous melatonin, core body temperature, cortisol) to
1575:
in seasonal animals. In seasonal breeders that do not have long gestation periods and that mate during longer daylight hours, the melatonin signal controls the seasonal variation in their sexual physiology, and similar physiological effects can be induced by exogenous melatonin in animals including
725:
Visible light entering the eye and the cascading positive and negative signalling pathways to neuronal structures in the mamallian brain that may follow: When the eyes are exposed to sunlight, the pineal gland's melatonin production is suppressed, resulting in the secretion of hormones that promote
1794:
Naturally-occurring melatonin has been reported in foods including tart cherries to about 0.17–13.46 ng/g, bananas, plums, grapes, rice, cereals, herbs, olive oil, wine, and beer. The consumption of milk and sour cherries may improve sleep quality. When birds ingest melatonin-rich plant feed,
833:
is recognized, yet the specifics of these interactions remain inadequately defined. An anti-inflammatory effect appears to be the most significant. The efficacy of melatonin in disease treatment has been the subject of limited trials, with most available data deriving from small-scale, preliminary
2647:
While originally thought to be produced exclusively in and secreted from the vertebrate pineal gland , it is now known that the indole is present in many, perhaps all, vertebrate organs and in organs of all plants that have been investigated . That melatonin is not relegated solely to the pineal
2385:
Hence, one melatonin molecule and its associated metabolites could scavenge a large number of reactive species, and thus, the overall antioxidant capacity of melatonin is believed to be greater than that of other well-known antioxidants, such as vitamin C and vitamin E, under in vitro or in vivo
1645:
Until its identification in plants in 1987, melatonin was for decades thought to be primarily an animal neurohormone. When melatonin was identified in coffee extracts in the 1970s, it was believed to be a byproduct of the extraction process. Subsequently, however, melatonin has been found in all
1292:
range, inhibits the biosynthesis of melatonin, with the degree of suppression being directly proportional to the intensity and duration of light exposure. Historically, humans in temperate climates experienced limited exposure to blue daylight during winter months, primarily receiving light from
1297:
used extensively throughout the 20th century emitted relatively low levels of blue light. It has been found that light containing only wavelengths greater than 530 nm does not suppress melatonin under bright-light conditions. The use of glasses that block blue light in the hours preceding
1414:(JAMA) in April 2023 found that a 12% of the 30 melatonin product preparations analyzed had melatonin quantities within ±10% of the amounts specified on their labels. Some supplements were found to contain up to 347% of the declared melatonin content. In Europe, melatonin is classified as an
1649:
Although a role for melatonin as a plant hormone has not been clearly established, its involvement in processes such as growth and photosynthesis is well established. Only limited evidence of endogenous circadian rhythms in melatonin levels has been demonstrated in some plant species and no
1776:
Melatonin is produced by α-proteobacteria and photosynthetic cyanobacteria. There is no report of its occurrence in archaea which indicates that melatonin originated in bacteria most likely to prevent the first cells from the damaging effects of oxygen in the primitive Earth's atmosphere.
746:
observed between midnight and 8:00 am. It has been documented that melatonin production diminishes as a person ages. Additionally, a shift in the timing of melatonin secretion is observed during adolescence, resulting in delayed sleep and wake times, increasing their risk for
2532:
melatonin is specifically targeted to the mitochondria where it seems to function as an apex antioxidant ... The measurement of the subcellular distribution of melatonin has shown that the concentration of this indole in the mitochondria greatly exceeds that in the
1422:
practices. A preceding study from 2022 concluded that consuming unregulated melatonin products can expose individuals, including children, to melatonin quantities ranging from 40 to 130 times higher than the recommended levels when products are used 'as directed'.
790:
antioxidant, in combating oxidative stress. The promotion of antioxidant enzyme expression, such as superoxide dismutase, glutathione peroxidase, glutathione reductase, and catalase, is mediated through melatonin receptor-triggered signal transduction pathways.
5907:"Ingestion of Japanese plums (Prunus salicina Lindl. cv. Crimson Globe) increases the urinary 6-sulfatoxymelatonin and total antioxidant capacity levels in young, middle-aged and elderly humans: Nutritional and functional characterization of their content"
3563:
Sumi-Ichinose C, Ichinose H, Takahashi E, Hori T, Nagatsu T (March 1992). "Molecular cloning of genomic DNA and chromosomal assignment of the gene for human aromatic L-amino acid decarboxylase, the enzyme for catecholamine and serotonin biosynthesis".
2931:
Poeggeler B, Saarela S, Reiter RJ, Tan DX, Chen LD, Manchester LC, Barlow-Walden LR (November 1994). "Melatonin—a highly potent endogenous radical scavenger and electron donor: new aspects of the oxidation chemistry of this indole accessed in vitro".
834:
studies. It is posited that any beneficial immunological impact is attributable to melatonin's action on high-affinity receptors (MT1 and MT2), which are present on immunocompetent cells. Preclinical investigations suggest that melatonin may augment
1298:
bedtime can mitigate melatonin suppression. Additionally, wearing blue-blocking goggles during the last hours before bedtime is recommended for individuals needing to adjust to an earlier bedtime since melatonin facilitates the onset of sleep.
1562:
In humans, ~30 μg of melatonin is produced daily and 80% of the total amount is produced in the night. The plasma maximum concentration of melatonin at night are 80–120 pg/mL and the concentrations during the day are between 10–20 pg/mL.
712:
activated by the binding of melatonin to its receptors. Through these mechanisms, melatonin protects the cell against oxidative stress in two ways, and plays other roles in human health than only regulating the sleep-wake cycle.
6055:
Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, et al. (March 1995). "Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates".
5671:
Socaciu AI, Ionuţ R, Socaciu MA, Ungur AP, Bârsan M, Chiorean A, et al. (December 2020). "Melatonin, an ubiquitous metabolic regulator: functions, mechanisms and effects on circadian disruption and degenerative diseases".
1469:, they extracted and identified melatonin from bovine pineal gland extracts. Subsequent research in the mid-1970s by Lynch and others demonstrated that melatonin production follows a circadian rhythm in human pineal glands.
862:
and body weight by signaling satiety and reducing food intake. Melatonin, by modulating leptin's actions outside of waking hours, may contribute to the restoration of leptin sensitivity during daytime, thereby counteracting
1124:
Alternatively, the second mechanism proposes that oxygen interacts with the active site iron (II) first, forming iron (III) superoxide. This molecule could then react with THB to form an iron-peroxypterin intermediate.
1116:
to form 4a-peroxypterin. 4a-peroxypterin may either react with the active site iron (II) to create an iron-peroxypterin intermediate or directly transfer an oxygen atom to the iron, facilitating the hydroxylation of
1795:
such as rice, the melatonin binds to melatonin receptors in their brains. When humans consume foods rich in melatonin, such as banana, pineapple, and orange, the blood levels of melatonin increase significantly.
741:
In mammals, melatonin is critical for the regulation of sleep–wake cycles, or circadian rhythms. The establishment of regular melatonin levels in human infants occurs around the third month after birth, with
5870:
Burkhardt S, Tan DX, Manchester LC, Hardeland R, Reiter RJ (October 2001). "Detection and quantification of the antioxidant melatonin in
Montmorency and Balaton tart cherries (Prunus cerasus)".
5928:
Lamont KT, Somers S, Lacerda L, Opie LH, Lecour S (May 2011). "Is red wine a SAFE sip away from cardioprotection? Mechanisms involved in resveratrol- and melatonin-induced cardioprotection".
2078:
Reiter RJ, Acuña-Castroviejo D, Tan DX, Burkhardt S (June 2001). "Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system".
805:
Furthermore, the interaction of melatonin with reactive oxygen and nitrogen species results in the formation of metabolites capable of reducing free radicals. These metabolites, including
1518:
effect. Melatonin was thus aptly named to reflect its role in preventing the darkening of the skin, highlighting the intersection of biochemistry and linguistics in scientific discovery.
1271:(AANAT), the penultimate enzyme in the melatonin synthesis pathway. When exposed to daylight, noradrenergic stimulation ceases, leading to the immediate degradation of the protein by
1089:(THB) to react with oxygen and the active site iron of tryptophan hydroxylase. Although the complete mechanism is not entirely understood, two main mechanisms have been proposed:
7053:
591:
within cells, are the main producers of antioxidant melatonin, underscoring the molecule's "ancient origins" and its fundamental role in protecting the earliest cells from
7341:
3148:
Carrillo-Vico A, Reiter RJ, Lardone PJ, Herrera JL, Fernández-Montesinos R, Guerrero JM, Pozo D (May 2006). "The modulatory role of melatonin on immune responsiveness".
726:
wakefulness. Conversely, in the absence of light, the pineal gland synthesizes melatonin unabated, leading to feelings of drowsiness and facilitating the onset of sleep.
5166:
Chen HJ (July 1981). "Spontaneous and melatonin-induced testicular regression in male golden hamsters: augmented sensitivity of the old male to melatonin inhibition".
1026:, and plants, the synthesis of melatonin also involves tryptophan as an intermediate but originates indirectly from the shikimate pathway. The pathway commences with
2909:
1047:. While the subsequent biosynthetic reactions share similarities with those in animals, there are slight variations in the enzymes involved in the final stages.
5472:
Park S, Lee DE, Jang H, Byeon Y, Kim YS, Back K (April 2013). "Melatonin-rich transgenic rice plants exhibit resistance to herbicide-induced oxidative stress".
3958:
1551:
of the eyes rather than the melatonin signal (as was once postulated). Known as "the hormone of darkness", the onset of melatonin at dusk promotes activity in
6480:
6452:
6349:
3467:"Mitochondria and chloroplasts as the original sites of melatonin synthesis: a hypothesis related to melatonin's primary function and evolution in eukaryotes"
1418:, highlighting the regulatory oversight of its use and distribution. Conversely, as of 2022, the United States was considering the inclusion of melatonin in
404:
1411:
2648:
gland is also emphasized by the reports that it is present in invertebrates , which lack a pineal gland and some of which consist of only a single cell.
4602:, Wurtman RJ, "Methods of inducing sleep using melatonin", issued 12 September 1995, assigned to Massachusetts Institute of Technology
5345:
Reiter RJ, Manchester LC, Tan DX (September 2005). "Melatonin in walnuts: influence on levels of melatonin and total antioxidant capacity of blood".
1494:
1351:
603:
40:
6308:
810:
4338:
3310:
7245:
6983:
2035:
Hardeland R (July 2005). "Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance".
7396:
7283:
6550:
4460:
3611:
1935:
1477:
782:
with other antioxidants, enhancing the overall effectiveness of each antioxidant. This compound has been found to be twice as efficacious as
6232:
5310:
Bonnefont-Rousselot D, Collin F (November 2010). "Melatonin: action as antioxidant and potential applications in human disease and aging".
3919:"Blocking low-wavelength light prevents nocturnal melatonin suppression with no adverse effect on performance during simulated shift work"
7619:
7591:
5819:
Arnao MB, Giraldo-Acosta M, Castejón-Castillejo A, Losada-Lorán M, Sánchez-Herrerías P, El
Mihyaoui A, Cano A, Hernández-Ruiz J (2023).
6193:
3078:
Carrillo-Vico A, Guerrero JM, Lardone PJ, Reiter RJ (July 2005). "A review of the multiple actions of melatonin on the immune system".
3043:
Pieri C, Marra M, Moroni F, Recchioni R, Marcheselli F (1994). "Melatonin: a peroxyl radical scavenger more effective than vitamin E".
1058:
and defense mechanisms against oxidative stress, reflecting the molecule's ancient origins and its multifaceted roles across different
7240:
6165:
7250:
5017:"Simulated pharmacokinetics of inhaled caffeine and melatonin from existing products indicate the lack of dosimetric considerations"
4052:
Hardeland R, Poeggeler B, Srinivasan V, Trakht I, Pandi-Perumal SR, Cardinali DP (2008). "Melatonergic drugs in clinical practice".
993:
944:
379:
3430:
Hardeland R (February 2015). "Melatonin in plants and other phototrophs: advances and gaps concerning the diversity of functions".
135:
1318:, which is then conjugated with sulfate and excreted in urine as a waste product. It is primarily metabolized by the liver enzyme
6653:
5972:
1625:
have lost all the genes for melatonin synthesis as well as those for melatonin receptors. This is thought to be related to their
1415:
1376:
1264:
615:
6085:"Serum melatonin levels and antioxidant capacities after consumption of pineapple, orange, or banana by healthy male volunteers"
5574:"Effects of melatonin on lettuce plant growth, antioxidant enzymes and photosynthetic pigments under salinity stress conditions"
5206:"Genes lost during the transition from land to water in cetaceans highlight genomic changes associated with aquatic adaptations"
7210:
6227:
2773:
Ardura J, Gutierrez R, Andres J, Agapito T (2003). "Emergence and evolution of the circadian rhythm of melatonin in children".
1342:
For both research and clinical purposes, melatonin levels in humans can be determined through saliva or blood plasma analysis.
1257:
8766:
6759:
6382:
6318:
6212:
4888:
Perreau-Lenz S, Pévet P, Buijs RM, Kalsbeek A (January 2004). "The biological clock: the bodyguard of temporal homeostasis".
4450:
3218:
Suriagandhi V, Nachiappan V (January 2022). "Protective
Effects of Melatonin against Obesity-Induced by Leptin Resistance".
5905:
González-Flores D, Velardo B, Garrido M, González-Gómez D, Lozano M, Ayuso MC, Barriga C, Paredes SD, Rodríguez AB (2011).
5715:
Germann SM, Baallal
Jacobsen SA, Schneider K, Harrison SJ, Jensen NB, Chen X, Stahlhut SG, Borodina I, et al. (2016).
4365:
Filadelfi AM, Castrucci AM (May 1996). "Comparative aspects of the pineal/melatonin system of poikilothermic vertebrates".
3629:"Melatonin biosynthesis: the structure of serotonin N-acetyltransferase at 2.5 A resolution suggests a catalytic mechanism"
8272:
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6217:
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489:
8300:
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6826:
6568:
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1589:
1548:
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748:
709:
571:), which includes reproduction, fattening, molting, and hibernation. Its effects are mediated through the activation of
322:
7235:
8650:
6313:
6293:
2000:
Boutin JA, Audinot V, Ferry G, Delagrange P (August 2005). "Molecular tools to study melatonin pathways and actions".
1432:
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650:
560:
343:
5522:
Arnao MB, Hernández-Ruiz J (December 2014). "Melatonin: plant growth regulator and/or biostimulator during stress?".
8121:
1927:
ADHD: Non-Pharmacologic
Interventions, An Issue of Child and Adolescent Psychiatric Clinics of North America, E-Book
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7923:
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6939:
6821:
1241:
843:
3378:"Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources"
8758:
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8446:
8356:
8192:
8001:
7938:
7276:
6944:
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3984:
Burkhart K, Phelps JR (December 2009). "Amber lenses to block blue light and improve sleep: a randomized trial".
3750:
Schomerus C, Korf HW (December 2005). "Mechanisms regulating melatonin synthesis in the mammalian pineal organ".
2590:
There is credible evidence to suggest that melatonin should be classified as a mitochondria-targeted antioxidant.
1669:
1388:
1279:
1253:
858:, a hormone that serves as a long-term indicator of the body's energy status. Leptin is important for regulating
806:
771:
564:
245:
4556:
Lynch HJ, Wurtman RJ, Moskowitz MA, Archer MC, Ho MH (January 1975). "Daily rhythm in human urinary melatonin".
3899:
7858:
7191:
7186:
6573:
4818:
Reiter RJ (May 1991). "Pineal melatonin: cell biology of its synthesis and of its physiological interactions".
1764:
1676:
1294:
1199:
859:
283:
4238:"Comparative Review of Approved Melatonin Agonists for the Treatment of Circadian Rhythm Sleep-Wake Disorders"
1540:
5139:
Chaturvedi CM (1984). "Effect of
Melatonin on the Adrenl and Gonad of the Common Mynah Acridtheres tristis".
1901:
8485:
7823:
7734:
7729:
7531:
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6802:
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1272:
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1032:
1028:
759:
592:
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1128:
Following the formation of iron (IV) oxide from the iron-peroxypterin intermediate, this oxide selectively
233:
8754:
8161:
7903:
7704:
7391:
7300:
7292:
6648:
6625:
6377:
6158:
4193:
Riha RL (November 2018). "The use and misuse of exogenous melatonin in the treatment of sleep disorders".
2231:
Manchester LC, Coto-Montes A, Boga JA, Andersen LP, Zhou Z, Galano A, Vriend J, Tan DX, Reiter RJ (2015).
1754:
928:
697:
31:
8153:
2816:
Sack RL, Lewy AJ, Erb DL, Vollmer WM, Singer CM (1986). "Human melatonin production decreases with age".
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7928:
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7833:
7694:
7521:
6969:
1696:
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1001:
701:
289:
77:
8331:
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8101:
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388:
InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
8660:
8645:
8237:
4734:
Liebmann PM, Wölfler A, Felsner P, Hofer D, Schauenstein K (1997). "Melatonin and the immune system".
4599:
3670:"Human hydroxyindole-O-methyltransferase: presence of LINE-1 fragment in a cDNA clone and pineal mRNA"
2345:
Jockers R, Delagrange P, Dubocovich ML, Markus RP, Renault N, Tosini G, et al. (September 2016).
1465:. Motivated by the possibility that a substance from the pineal gland could be beneficial in treating
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1419:
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693:
646:
635:
175:
4691:
Beyer CE, Steketee JD, Saphier D (1998). "Antioxidant properties of melatonin–an emerging mystery".
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5058:"Clock genes in calendar cells as the basis of annual timekeeping in mammals—a unifying hypothesis"
2607:
Manchester LC, Coto-Montes A, Boga JA, Andersen LP, Zhou Z, Galano A, et al. (November 2015).
2138:"Functional roles of melatonin in plants, and perspectives in nutritional and agricultural science"
1585:
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893:
743:
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101:
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5821:"Melatonin from Microorganisms, Algae, and Plants as Possible Alternatives to Synthetic Melatonin"
3803:"Action spectrum for melatonin regulation in humans: evidence for a novel circadian photoreceptor"
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Tan DX, Hardeland R, Manchester LC, Korkmaz A, Ma S, Rosales-Corral S, Reiter RJ (January 2012).
2111:
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1982:
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572:
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Tordjman S, Chokron S, Delorme R, Charrier A, Bellissant E, Jaafari N, Fougerou C (April 2017).
7466:
7401:
7366:
7361:
5717:"Glucose-based microbial production of the hormone melatonin in yeast Saccharomyces cerevisiae"
4986:
Journal of
Physiology and Pharmacology: An Official Journal of the Polish Physiological Society
4291:"Drugs for Insomnia beyond Benzodiazepines: Pharmacology, Clinical Applications, and Discovery"
39:
This article is about melatonin as a hormone. For its role as a supplement and medication, see
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Tan DX, Manchester LC, Liu X, Rosales-Corral SA, Acuna-Castroviejo D, Reiter RJ (March 2013).
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1159:-tryptophan to produce 5-hydroxytryptamine is then facilitated by a decarboxylase enzyme with
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24:
3801:
Brainard GC, Hanifin JP, Greeson JM, Byrne B, Glickman G, Gerner E, Rollag MD (August 2001).
1472:
The first patent for the therapeutic use of melatonin as a low-dose sleep aid was awarded to
854:
Melatonin's potential to regulate weight gain is posited to involve its inhibitory effect on
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EL-Bauome HA, Doklega SM, Saleh SA, Mohamed AS, Suliman AA, Abd El-Hady MA (February 2024).
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1833:
1825:
1782:
1687:
1681:
1661:
1630:
1384:
1361:
955:
736:
681:
662:
642:
580:
568:
549:
509:
427:
7774:
331:
8845:
8428:
8086:
7219:
7011:
6754:
6387:
6182:
5980:
4286:
3263:"Narrative review: the role of leptin in human physiology: emerging clinical applications"
1874:"Evidence for the efficacy of melatonin in the treatment of primary adult sleep disorders"
1536:
1515:
1473:
1462:
1454:
1059:
936:
818:
779:
689:
533:
525:
8217:
3959:"University of Houston study shows blue light glasses at night increase melatonin by 58%"
2479:
2477:
2475:
195:
5221:
4569:
4493:
3917:
Kayumov L, Casper RF, Hawa RJ, Perelman B, Chung SA, Sokalsky S, Shapiro CM (May 2005).
3763:
3003:
2945:
2693:
2668:
2510:
2485:
2091:
1838:
1813:
602:
functions as a hormone and antioxidant, melatonin is also administered exogenously as a
364:
237:
155:
111:
64:
8546:
8489:
8477:
7943:
7386:
7356:
7091:
7063:
6906:
6875:
6847:
6792:
6687:
6404:
6335:
6136:
5847:
5820:
5741:
5716:
5408:
5381:
5238:
5205:
4957:
4932:
4378:
4262:
4237:
3876:
3851:
3827:
3818:
3802:
3707:
Nesbitt AD, Leschziner GD, Peatfield RC (September 2014). "Headache, drugs and sleep".
3540:
3515:
3402:
3377:
3353:
3328:
3287:
3262:
3020:
2987:
2953:
2885:
2860:
2829:
2750:
2725:
2456:
2429:
2371:
2346:
2311:
2284:
2205:
2178:
2099:
1718:
1568:
1368:
1314:
ranging from 20 to 50 minutes. The primary metabolic pathway transforms melatonin into
1261:
1245:
1044:
1040:
989:
607:
483:
5989:
5573:
4795:
4704:
4533:
4516:
3645:
3628:
3344:
2399:"Melatonin receptors | G protein-coupled receptors | IUPHAR/BPS Guide to Pharmacology"
1498:, Lerner and his colleagues proposed the name melatonin, derived from the Greek words
1240:
In vertebrates, the secretion of melatonin is regulated through the activation of the
8855:
8550:
8313:
7981:
7674:
7376:
7351:
6916:
6692:
6394:
6357:
5941:
5906:
5805:
5765:
5701:
5489:
4426:
4409:
4013:
3500:
3247:
3056:
2179:"Mitochondria: Central Organelles for Melatonin's Antioxidant and Anti-Aging Actions"
1969:
1952:
1723:
1651:
1605:
1511:
1466:
1211:
1176:
916:
830:
685:
471:
226:
5657:
5601:
5555:
5296:
4917:
4517:"Isolation of melatonin and 5-methoxyindole-3-acetic acid from bovine pineal glands"
4394:
4353:
4222:
4131:
4081:
3787:
3736:
3107:
2969:
2845:
2802:
2710:
2667:
Mayo JC, Sainz RM, González-Menéndez P, Hevia D, Cernuda-Cernuda R (November 2017).
2642:
2585:
2527:
2266:
2115:
2064:
1986:
1855:
817:(AMK), contribute to the broader antioxidative effects of melatonin through further
579:. In plants and bacteria, melatonin primarily serves as a defense mechanism against
8705:
8618:
8602:
8556:
8418:
8398:
8267:
8262:
8232:
8227:
8222:
8169:
7898:
7793:
7754:
7739:
7724:
7714:
7709:
7669:
7566:
7561:
7556:
7551:
7541:
7536:
7516:
7164:
6699:
6635:
6620:
6583:
6530:
6497:
6237:
6204:
5957:
5505:
5204:
Huelsmann M, Hecker N, Springer MS, Gatesy J, Sharma V, Hiller M (September 2019).
4861:
Richardson GS (2005). "The human circadian system in normal and disordered sleep".
4847:
4622:
4324:
3204:
2741:
1759:
1597:
1532:
1506:, meaning 'labour', 'colour' or 'suppress'. This naming convention follows that of
1492:
stems from its skin-lightening properties. As detailed in their publication in the
1447:
1070:
1051:
897:
889:
799:
775:
677:
627:
584:
537:
529:
6118:
5539:
1144:
of the hydrogen and the loss of one of the two hydrogen atoms on C5 would restore
880:
4206:
4099:
2486:"Melatonin as a mitochondria-targeted antioxidant: one of evolution's best ideas"
1571:) seasonal functions such as reproduction, behavior, coat growth, and camouflage
1531:
In vertebrates, melatonin is produced in darkness, thus usually at night, by the
1225:-acetylserotonin at the hydroxyl position by SAM, resulting in the production of
8802:
8614:
8594:
8542:
8455:
8413:
8408:
8388:
8383:
8365:
8287:
8212:
8197:
7918:
7749:
7719:
7664:
7581:
7546:
7526:
7511:
7149:
7124:
7109:
7058:
7021:
6992:
6883:
6860:
6362:
6265:
3091:
2550:
Reiter RJ, Mayo JC, Tan DX, Sainz RM, Alatorre-Jimenez M, Qin L (October 2016).
2048:
1829:
1609:
1601:
1577:
1567:
thus serves as a biological signal for the organization of daylength-dependent (
1458:
1404:
1400:
1307:
1275:
1191:
1172:
1145:
1137:
1133:
1129:
978:
924:
673:
576:
553:
505:
311:
5685:
5113:
2013:
1892:
1278:. The production of melatonin recommences in the evening, a phase known as the
721:
8794:
8785:
8762:
8744:
8715:
8710:
8690:
8606:
8598:
8576:
8517:
8465:
8441:
8436:
8393:
8252:
8060:
8055:
8050:
8020:
8006:
7996:
7908:
7808:
7779:
7654:
7644:
7634:
7604:
7501:
7486:
7451:
7346:
7139:
7129:
7119:
7114:
7086:
7076:
7033:
6911:
6797:
6447:
6399:
6328:
6323:
5781:
5398:
5358:
5323:
5033:
4778:
4478:"Evidences associating pineal gland function with alterations in pigmentation"
3997:
3393:
3231:
3188:
2684:
2501:
2285:"Melatonin Synthesis and Function: Evolutionary History in Animals and Plants"
2195:
1701:
1556:
1249:
1207:
1054:
suggests an evolutionary and functional significance of melatonin in cellular
974:
908:
787:
767:
599:
588:
521:
461:
186:
5789:
5042:
4993:
4755:
4712:
4646:
3720:
2484:
Reiter RJ, Rosales-Corral S, Tan DX, Jou MJ, Galano A, Xu B (November 2017).
2446:
2386:
conditions (Gitto et al., 2001; Sharma and Haldar, 2006; Ortiz et al., 2013).
2301:
8813:
8798:
8770:
8739:
8734:
8729:
8680:
8675:
8665:
8610:
8590:
8571:
8566:
8538:
8493:
8481:
8351:
8346:
8336:
8247:
8242:
8202:
8126:
8035:
7933:
7913:
7873:
7798:
7744:
7689:
7679:
7659:
7649:
7639:
7629:
7624:
7614:
7609:
7571:
7506:
7496:
7481:
7471:
7456:
7446:
7436:
7426:
7416:
7381:
7328:
7170:
7153:
7143:
7068:
7048:
7037:
7027:
6714:
6525:
6437:
6372:
6298:
6032:
6015:
5592:
5380:
Reiter RJ, Tan DX, Zhou Z, Cruz MH, Fuentes-Broto L, Galano A (April 2015).
5016:
4981:
4577:
3771:
3685:
1657:
1552:
1507:
1444:
1396:
1288:
1221:
The final step in the biosynthesis of melatonin involves the methylation of
1195:
1187:
1141:
1078:
The mechanism of melatonin biosynthesis initiates with the hydroxylation of
948:
783:
639:
513:
6110:
6041:
5949:
5891:
5856:
5837:
5797:
5750:
5732:
5693:
5649:
5547:
5497:
5458:
5417:
5366:
5331:
5288:
5247:
5229:
5121:
5083:
5001:
4966:
4948:
4909:
4874:
4804:
4623:"Isolation of melatonin, the pineal gland factor that lightens melanocytes"
4542:
4501:
4435:
4316:
4271:
4214:
4179:
4123:
4115:
4073:
4065:
4005:
3944:
3885:
3836:
3779:
3728:
3654:
3549:
3492:
3451:
3411:
3362:
3296:
3239:
3196:
3175:
Maestroni GJ (March 2001). "The immunotherapeutic potential of melatonin".
3161:
3134:
3099:
3029:
2894:
2794:
2759:
2702:
2634:
2577:
2519:
2465:
2380:
2320:
2258:
2214:
2163:
2107:
2056:
2021:
1978:
1910:
1847:
1510:, another agent affecting skin color, discovered in 1948 as a modulator of
6069:
5261:
Paredes SD, Korkmaz A, Manchester LC, Tan DX, Reiter RJ (1 January 2009).
5187:
5074:
5057:
4901:
4839:
4831:
4763:
4720:
4677:
4585:
4386:
4307:
4290:
3693:
3668:
Donohue SJ, Roseboom PH, Illnerova H, Weller JL, Klein DC (October 1993).
3585:
3064:
2961:
2837:
2609:"Melatonin: an ancient molecule that makes oxygen metabolically tolerable"
2233:"Melatonin: an ancient molecule that makes oxygen metabolically tolerable"
8808:
8685:
8670:
8586:
8581:
8534:
8509:
8497:
8451:
8403:
8030:
8015:
7883:
7878:
7476:
7461:
7441:
7431:
7421:
7411:
7406:
7318:
7313:
7134:
7043:
6865:
6764:
6746:
6704:
6682:
6605:
6597:
6578:
6560:
6489:
6367:
6260:
6222:
5764:
Luo H, Schneider K, Christensen U, Lei Y, Herrgard M, Palsson BØ (2020).
5531:
5279:
5262:
3935:
3918:
3443:
3376:
Bochkov DV, Sysolyatin SV, Kalashnikov AI, Surmacheva IA (January 2012).
3011:
2861:"Adolescent changes in the homeostatic and circadian regulation of sleep"
2724:
Emet M, Ozcan H, Ozel L, Yayla M, Halici Z, Hacimuftuoglu A (June 2016).
2428:
Sharafati-Chaleshtori R, Shirzad H, Rafieian-Kopaei M, Soltani A (2017).
2154:
2137:
1713:
1622:
1372:
1093:
1019:
1015:
835:
763:
755:
705:
611:
517:
206:
4638:
4027:
3867:
3577:
1194:
the primary amine of 5-hydroxytryptamine. This deprotonation allows the
215:
8790:
8505:
8501:
8375:
8341:
8174:
8045:
7764:
7759:
7159:
6769:
6736:
6731:
6723:
6610:
6545:
6416:
6174:
2662:
2660:
2658:
2656:
1634:
1327:
1050:
The hypothesis that melatonin synthesis occurs within mitochondria and
754:
The antioxidant properties of melatonin were first recognized in 1993.
541:
298:
246:
20:
6101:
6084:
6016:"Influence of Dietary Sources of Melatonin on Sleep Quality: A Review"
5640:
5619:
5449:
5432:
5179:
5152:
4747:
4253:
4170:
4153:
3483:
3466:
2876:
2786:
2625:
2608:
2568:
2551:
2362:
2340:
2338:
2336:
2334:
2332:
2330:
2249:
2232:
89:
5-Methoxy-N-acetyltryptamine; N-Acetyl-5-methoxytryptamine; NSC-113928
55:
8818:
8720:
8530:
7991:
7953:
7888:
7853:
7848:
7769:
6893:
6855:
6674:
6615:
5883:
4449:
Coates PM, Blackman MR, Cragg GM, Levine M, Moss J, White JD (2005).
3531:
2177:
Reiter RJ, Tan DX, Rosales-Corral S, Galano A, Zhou XJ, Xu B (2018).
1675:
Fungal disease resistance is another role. Added melatonin increases
1616:
1581:
1331:
1323:
1319:
1175:
of the amine derived from tryptophan restores the aromaticity of the
1008:
855:
839:
708:. This increase in antioxidant enzyme expression is mediated through
166:
6014:
Pereira N, Naufel MF, Ribeiro EB, Tufik S, Hachul H (January 2020).
3669:
1293:
sources that emitted predominantly yellow light, such as fires. The
482:
Except where otherwise noted, data are given for materials in their
5100:
Arendt J, Skene DJ (February 2005). "Melatonin as a chronobiotic".
4339:"Quantity of Melatonin and CBD in Melatonin Gummies Sold in the US"
1872:
Auld F, Maschauer EL, Morrison I, Skene DJ, Riha RL (August 2017).
272:
8749:
8561:
8025:
6926:
6901:
6812:
6784:
6517:
4779:"Serum vasoconstrictor, serotonin; isolation and characterization"
4236:
Williams WP, McLin DE, Dressman MA, Neubauer DN (September 2016).
1203:
1164:
1069:
1023:
879:
649:, with nanomolar binding affinity. Both receptors are part of the
545:
528:
and colleagues stemmed from the isolation of a substance from the
146:
134:
124:
5127:
earlier (advance phase shift) or later (delay phase shift) times.
4410:"Melatonin, melatonin receptors and melanophores: a moving story"
3852:"What's in a color? The unique human health effect of blue light"
2283:
Zhao D, Yu Y, Shen Y, Liu Q, Zhao Z, Sharma R, Reiter RJ (2019).
1167:
with the amino acid derivative, facilitating the breaking of the
661:
GPCRs, although melatonin receptor 1 also exhibits coupling with
7893:
7863:
7813:
2908:
Tan DX, Chen LD, Poeggeler B, L Manchester C, Reiter RJ (1993).
915:. The initial step in the melatonin biosynthesis pathway is the
654:
263:
7265:
6965:
6961:
6147:
5766:"Microbial Synthesis of Human-Hormone Melatonin at Gram Scales"
3261:
Kelesidis T, Kelesidis I, Chou S, Mantzoros CS (January 2010).
2552:"Melatonin as an antioxidant: under promises but over delivers"
7261:
4337:
Cohen PA, Avula B, Wang Y, Katragunta K, Khan I. (April 2023)
1248:. Norepinephrine increases the concentration of intracellular
3329:"Melatonin: Pharmacology, Functions and Therapeutic Benefits"
2859:
Hagenauer MH, Perryman JI, Lee TM, Carskadon MA (June 2009).
5613:
5611:
5517:
5515:
4666:
2910:"Melatonin: a potent, endogenous hydroxyl radical scavenger"
1179:, leading to the production of 5-hydroxytryptamine and PLP.
348:
6143:
758:
studies reveal that melatonin directly neutralizes various
548:
during the night, playing a crucial role in regulating the
6083:
Sae-Teaw M, Johns J, Johns NP, Subongkot S (August 2013).
2545:
2543:
2541:
1752:
Melatonin has been observed to reduce stress tolerance in
4154:"A critical review of melatonin assays: Past and present"
1758:
in plant-pathogen systems. Danish pharmaceutical company
1600:
season when daylight hours are long. The reproduction of
5382:"Phytomelatonin: assisting plants to survive and thrive"
4621:
Lerner AB, Case JD, Takahashi Y, Lee TH, Mori W (1958).
5015:
Kolli AR, Kuczaj AK, Calvino-Martin F, Hoeng J (2024).
4408:
Sugden D, Davidson K, Hough KA, Teh MT (October 2004).
563:
sleep-wake cycles, encompassing sleep-wake timing and
8829:
1112:). This superoxide could then recombine with the THB
5586:(1). Polish Society of Horticultural Science: 1–17.
4098:
Ma X, Idle JR, Krausz KW, Gonzalez FJ (April 2005).
3923:
The
Journal of Clinical Endocrinology and Metabolism
1443:
skin of tadpoles to lighten by contracting the dark
1140:
at the C5 position of the indole ring. A subsequent
1092:
The first mechanism involves a slow transfer of one
672:
Furthermore, melatonin functions as a high-capacity
8628:
8427:
8374:
8183:
8074:
7299:
7228:
7179:
6999:
6925:
6892:
6874:
6846:
6811:
6783:
6745:
6722:
6713:
6673:
6666:
6634:
6596:
6559:
6516:
6488:
6479:
6461:
6415:
6348:
6274:
6251:
6203:
6192:
6181:
4100:"Metabolism of Melatonin by Human Cytochromes P450"
3604:
Medicinal
Natural Products. A Biosynthetic Approach
3516:"Mechanisms of tryptophan and tyrosine hydroxylase"
2988:"The physiological function of melatonin in plants"
2981:
2979:
1539:located in the center of the brain but outside the
5056:Lincoln GA, Andersson H, Loudon A (October 2003).
1814:"A brief review about melatonin, a pineal hormone"
4662:"Melatonin: Historical and Clinical Perspectives"
4455:. New York, N.Y: Marcel Dekker. pp. 457–66.
2347:"Update on melatonin receptors: IUPHAR Review 20"
1953:"Melatonin: therapeutic and clinical utilization"
1902:20.500.11820/0e890bda-4b1d-4786-a907-a03b1580fd07
1391:. In addition to melatonin, a range of synthetic
6058:Biochemistry and Molecular Biology International
5199:
5197:
4736:International Archives of Allergy and Immunology
3425:
3423:
3421:
3123:Eksperimental'naia i Klinicheskaia Farmakologiia
2726:"A Review of Melatonin, Its Receptors and Drugs"
626:In humans, melatonin primarily acts as a potent
583:, indicating its evolutionary significance. The
559:In vertebrates, melatonin's functions extend to
310:
4777:Rapport MM, Green AA, Page IH (December 1948).
2602:
2600:
2598:
2423:
2421:
2419:
1514:, which influenced its name based on its serum
892:of melatonin in animals involves a sequence of
798:is significantly higher than that found in the
567:, as well as controlling seasonal rhythmicity (
110:
5674:Reviews in Endocrine & Metabolic Disorders
3311:"MetaCyc serotonin and melatonin biosynthesis"
1633:at a time). Similar trends have been found in
1453:The hormone melatonin was isolated in 1958 by
7277:
6977:
6159:
5618:Arnao MB, Hernández-Ruiz J (September 2015).
5431:Arnao MB, Hernández-Ruiz J (September 2015).
5095:
5093:
4515:Lerner AB, Case JD, Takahashi Y (July 1960).
4093:
4091:
3627:Hickman AB, Klein DC, Dyda F (January 1999).
3597:
3595:
1198:on the amine to attack acetyl-CoA, forming a
977:. The final step in the pathway involves the
8:
5620:"Functions of melatonin in plants: a review"
5433:"Functions of melatonin in plants: a review"
3900:"Recent News – Program of Computer Graphics"
3322:
3320:
2430:"Melatonin and human mitochondrial diseases"
1780:Novo Nordisk have used genetically modified
1717:spp. Decreases the speed of infection. As a
680:, playing a dual role in combating cellular
1412:Journal of the American Medical Association
1214:when attacked by a general base, producing
7284:
7270:
7262:
6984:
6970:
6962:
6719:
6670:
6485:
6200:
6189:
6166:
6152:
6144:
5872:Journal of Agricultural and Food Chemistry
3752:Annals of the New York Academy of Sciences
2934:Annals of the New York Academy of Sciences
2131:
2129:
2127:
2125:
2080:Annals of the New York Academy of Sciences
1957:International Journal of Clinical Practice
1867:
1865:
692:of essential antioxidant enzymes, such as
540:. This compound was later identified as a
363:
236:
194:
47:
6100:
6031:
5846:
5836:
5740:
5639:
5591:
5448:
5407:
5397:
5278:
5237:
5073:
5032:
4956:
4794:
4532:
4425:
4306:
4261:
4169:
3934:
3875:
3826:
3644:
3539:
3514:Roberts KM, Fitzpatrick PF (April 2013).
3482:
3401:
3352:
3286:
3019:
2884:
2749:
2692:
2624:
2567:
2509:
2455:
2445:
2370:
2310:
2300:
2248:
2204:
2194:
2153:
1968:
1930:. Elsevier Health Sciences. p. 888.
1900:
1837:
1596:gland, especially in mammals that have a
1082:-tryptophan, a process that requires the
552:, also known as the circadian rhythm, in
330:
5973:"Melatonin in Medicinal and Food Plants"
4627:Journal of the American Chemical Society
3150:Current Opinion in Investigational Drugs
1818:Archives of Endocrinology and Metabolism
1495:Journal of the American Chemical Society
1352:Melatonin as a medication and supplement
838:production and promote the expansion of
720:
41:Melatonin as a medication and supplement
8836:
3279:10.7326/0003-4819-152-2-201001190-00008
3177:Expert Opinion on Investigational Drugs
2986:Arnao MB, Hernández-Ruiz J (May 2006).
2669:"Melatonin transport into mitochondria"
2434:Journal of Research in Medical Sciences
1804:
1100:), potentially producing a superoxide (
935:(5-HTP). Subsequently, 5-HTP undergoes
903:, which can be synthesized through the
811:N1-acetyl-N2-formyl-5-methoxykynuramine
409:
384:
359:
288:
214:
5911:Journal of Food and Nutrition Research
4660:Goeser S, Ruble J, Chandler L (1997).
1762:have used genetically modified yeast (
1615:During the night, melatonin regulates
227:
5567:
5565:
4933:"Sleep, circadian rhythms and health"
4616:
4614:
2278:
2276:
2226:
2224:
1580:and hamsters. Melatonin can suppress
1543:. Light/dark information reaches the
1478:Massachusetts Institute of Technology
606:. It is utilized in the treatment of
391:Key: DRLFMBDRBRZALE-UHFFFAOYSA-N
174:
154:
7:
7685:5-Methoxytryptamine (5-MT; mexamine)
4476:McCord CP, Allen FP (January 1917).
3121:Arushanian EB, Beĭer EV (2002). "".
2673:Cellular and Molecular Life Sciences
2490:Cellular and Molecular Life Sciences
1555:(night-active) animals and sleep in
911:, found in plants, or obtained from
676:, or free radical scavenger, within
16:Hormone released by the pineal gland
4783:The Journal of Biological Chemistry
4521:The Journal of Biological Chemistry
4452:Encyclopedia of dietary supplements
1190:residue His122, is hypothesized to
1171:and release of carbon dioxide. The
1074:Mechanism of melatonin biosynthesis
778:(NO•). In plants, melatonin works
684:. Firstly, it directly neutralizes
301:
271:
4863:The Journal of Clinical Psychiatry
4379:10.1111/j.1600-079X.1996.tb00256.x
3819:10.1523/JNEUROSCI.21-16-06405.2001
2954:10.1111/j.1749-6632.1994.tb21831.x
2830:10.1111/j.1600-079X.1986.tb00760.x
2100:10.1111/j.1749-6632.2001.tb03627.x
2002:Trends in Pharmacological Sciences
1951:Altun A, Ugur-Altun B (May 2007).
1812:Amaral FG, Cipolla-Neto J (2018).
1664:has been experimentally mitigated
1346:Use as a medication and supplement
1285:Blue light, especially within the
1163:(PLP) as a cofactor. PLP forms an
14:
3856:Environmental Health Perspectives
3345:10.2174/1570159X14666161228122115
1502:, meaning 'black' or 'dark', and
1155:The decarboxylation of 5-hydroxy-
945:5-hydroxytryptophan decarboxylase
842:, thereby potentially mitigating
829:Melatonin's interaction with the
794:Melatonin's concentration in the
653:(GPCRs) family, specifically the
604:dietary supplement and medication
8839:
6654:5-Methoxy-N,N-dimethyltryptamine
5942:10.1111/j.1600-079X.2010.00853.x
5490:10.1111/j.1600-079x.2012.01029.x
4427:10.1111/j.1600-0749.2004.00185.x
2730:The Eurasian Journal of Medicine
1970:10.1111/j.1742-1241.2006.01191.x
1416:active pharmaceutical ingredient
1377:circadian rhythm sleep disorders
931:, resulting in the formation of
688:, and secondly, it promotes the
616:circadian rhythm sleep disorders
445:
439:
63:
54:
7967:-Feruloylserotonin (moschamine)
4104:Drug Metabolism and Disposition
2351:British Journal of Pharmacology
1727:from fungi. Dramatically slows
1258:cAMP-dependent protein kinase A
1096:from THB to molecular oxygen (O
486:(at 25 °C , 100 kPa).
8122:6,7-Dichloro-2-methylmelatonin
5267:Journal of Experimental Botany
4352::10.1001/jama.2023.2296. PMID
3432:Journal of Experimental Botany
2992:Plant Signaling & Behavior
2742:10.5152/eurasianjmed.2015.0267
2142:Journal of Experimental Botany
1256:, which in turn activates the
451:
433:
412:CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC
1:
5540:10.1016/j.tplants.2014.07.006
5141:Australian Journal of Zoology
4980:Karasek M, Winczyk K (2006).
4796:10.1016/S0021-9258(18)57137-4
4705:10.1016/s0006-2952(98)00180-4
4534:10.1016/S0021-9258(18)69351-2
3646:10.1016/S1097-2765(00)80171-9
1549:photosensitive ganglion cells
1043:cells, additionally involves
1011:donor, to produce melatonin.
815:N1-acetyl-5-methoxykynuramine
8278:α-Methylserotonin (5-HO-αMT)
7785:Benzotript (4-chlorobenzoyl-
5062:The Journal of Endocrinology
5021:Food and Chemical Toxicology
4207:10.1097/MCP.0000000000000522
3057:10.1016/0024-3205(94)00666-0
1612:is stimulated by melatonin.
1590:follicle-stimulating hormone
1381:delayed sleep phase disorder
1356:Melatonin is used both as a
958:, is further converted into
749:delayed sleep phase disorder
710:signal transduction pathways
8011:-acetylpsilocin; 4-AcO-DMT)
4890:Chronobiology International
4869:(Suppl 9): 3–9, quiz 42–3.
4152:Kennaway DJ (August 2019).
3986:Chronobiology International
3850:Holzman DC (January 2010).
3807:The Journal of Neuroscience
3382:Journal of Chemical Biology
3267:Annals of Internal Medicine
2403:www.guidetopharmacology.org
1830:10.20945/2359-3997000000066
1730:Pseudomonas syringae tomato
1584:by inhibiting secretion of
1461:professor, and his team at
1433:History of the pineal gland
1393:melatonin receptor agonists
844:acquired immunodeficiencies
651:G-protein coupled receptors
524:. Its discovery in 1958 by
466:232.281 g/mol
8878:
6822:Insulin-like growth factor
6089:Journal of Pineal Research
5930:Journal of Pineal Research
5686:10.1007/s11154-020-09570-9
5624:Journal of Pineal Research
5474:Journal of Pineal Research
5437:Journal of Pineal Research
5263:"Phytomelatonin: a review"
5114:10.1016/j.smrv.2004.05.002
4367:Journal of Pineal Research
4158:Journal of Pineal Research
3471:Journal of Pineal Research
3220:Behavioural Brain Research
2865:Developmental Neuroscience
2818:Journal of Pineal Research
2613:Journal of Pineal Research
2556:Journal of Pineal Research
2289:Frontiers in Endocrinology
2237:Journal of Pineal Research
2014:10.1016/j.tips.2005.06.006
1893:10.1016/j.smrv.2016.06.005
1430:
1349:
1322:and to a lesser extent by
1242:beta-1 adrenergic receptor
734:
532:of cows that could induce
38:
18:
8283:α-Methyltryptophan (αMTP)
5782:10.1021/acssynbio.0c00065
5399:10.3390/molecules20047396
5359:10.1016/j.nut.2005.02.005
5324:10.1016/j.tox.2010.04.008
5034:10.1016/j.fct.2024.114601
3998:10.3109/07420520903523719
3394:10.1007/s12154-011-0064-8
3333:Current Neuropharmacology
3232:10.1016/j.bbr.2021.113598
3189:10.1517/13543784.10.3.467
2685:10.1007/s00018-017-2616-8
2502:10.1007/s00018-017-2609-7
2196:10.3390/molecules23020509
1410:A study published by the
1389:shift work sleep disorder
1280:dim-light melatonin onset
1254:beta-adrenergic receptors
1186:-acetyltransferase, with
807:cyclic 3-hydroxymelatonin
772:reactive nitrogen species
565:blood pressure regulation
480:
420:
400:
375:
94:
86:
76:
71:
62:
53:
30:. For the video game see
7192:Butylated hydroxytoluene
7187:Butylated hydroxyanisole
5971:Salehi B (5 July 2019).
4693:Biochemical Pharmacology
3904:www.graphics.cornell.edu
3721:10.1177/0333102414542662
2447:10.4103/1735-1995.199092
2302:10.3389/fendo.2019.00249
1768:) to produce melatonin.
1765:Saccharomyces cerevisiae
1608:and the reproduction of
1407:, are used in medicine.
1295:incandescent light bulbs
1200:tetrahedral intermediate
954:Serotonin, an essential
19:Not to be confused with
8755:Substituted benzofurans
8490:β-carboline (norharman)
8337:AL-37350A (4,5-DHP-αMT)
7824:Desformylflustrabromine
7755:Aeruginascin (4-PO-TMT)
6033:10.1111/1750-3841.14952
6020:Journal of Food Science
5593:10.2478/fhort-2024-0001
5524:Trends in Plant Science
4931:Foster RG (June 2020).
4578:10.1126/science.1167425
3772:10.1196/annals.1356.028
3686:10.1089/dna.1993.12.715
3606:(2nd ed.). Wiley.
1619:, lowering its levels.
1559:ones including humans.
1358:prescription medication
760:reactive oxygen species
593:reactive oxygen species
8141:-acetylserotonin; NAS)
7982:Norbaeocystin (4-PO-T)
7705:5-(Nonyloxy)tryptamine
6649:N,N-Dimethyltryptamine
6626:Pancreatic polypeptide
5838:10.3390/metabo13010072
5733:10.1002/biot.201500143
5230:10.1126/sciadv.aaw6671
5102:Sleep Medicine Reviews
4949:10.1098/rsfs.2019.0098
4502:10.1002/jez.1400230108
4116:10.1124/dmd.104.002410
4066:10.1055/s-0031-1296459
1881:Sleep Medicine Reviews
1786:to produce melatonin.
1755:Phytophthora infestans
1606:repressed by melatonin
1545:suprachiasmatic nuclei
1367:for the management of
1230:-adenosyl homocysteine
1148:, producing 5-hydroxy-
1075:
1033:-erythrose 4-phosphate
929:tryptophan hydroxylase
885:
884:Melatonin biosynthesis
727:
698:glutathione peroxidase
8531:DM-506 (ibogaminalog)
8203:4-HO-MPMI (lucigenol)
8021:Psilocybin (4-PO-DMT)
7929:Methylbutyltryptamine
7780:Baeocystin (4-PO-NMT)
5770:ACS Synthetic Biology
5721:Biotechnology Journal
5075:10.1677/joe.0.1790001
4988:. 57 Suppl 5: 19–39.
4982:"Melatonin in humans"
4902:10.1081/CBI-120027984
4832:10.1210/edrv-12-2-151
4678:10.1300/J088v05n01_04
4600:US patent 5449683
4414:Pigment Cell Research
4308:10.1124/pr.117.014381
4054:Arzneimittelforschung
3092:10.1385/ENDO:27:2:189
2049:10.1385/ENDO:27:2:119
1741:Nicotiana benthamiana
1312:elimination half-life
1232:(SAH) and melatonin.
1073:
883:
724:
702:glutathione reductase
23:. For the album, see
8429:Cyclized tryptamines
7934:Miprocin (4-HO-MiPT)
7904:Indolylethylfentanyl
7874:Ethocybin (4-PO-DET)
7799:Bufotenin (5-HO-DMT)
7794:Bufotenidine (5-HTQ)
3936:10.1210/jc.2004-2062
3674:DNA and Cell Biology
3012:10.4161/psb.1.3.2640
1734:Arabidopsis thaliana
1668:in a high-melatonin
1627:unihemispheric sleep
1420:pharmacy compounding
1005:-adenosyl methionine
821:with free radicals.
796:mitochondrial matrix
751:during this period.
717:Biological functions
694:superoxide dismutase
647:melatonin receptor 2
636:melatonin receptor 1
512:produced by various
8529:and related (e.g.,
8165:-Propionylmelatonin
8016:Psilocin (4-HO-DMT)
7914:Iprocin (4-HO-DiPT)
6935:Natriuretic peptide
6253:Posterior pituitary
6238:Somatostatin (GHIH)
5995:on 29 November 2021
5579:Folia Horticulturae
5222:2019SciA....5.6671H
4639:10.1021/ja01543a060
4570:1975Sci...187..169L
4494:1917JEZ....23..207M
3868:10.1289/ehp.118-a22
3764:2005NYASA1057..372S
3578:10.1021/bi00123a004
3004:2006PlSiB...1...89A
2946:1994NYASA.738..419P
2092:2001NYASA.939..200R
1924:Faraone SV (2014).
1586:luteinizing hormone
1541:blood–brain barrier
1161:pyridoxal phosphate
1087:tetrahydrobiopterin
1037:phosphoenolpyruvate
941:pyridoxal phosphate
933:5-hydroxytryptophan
894:enzymatic reactions
744:peak concentrations
632:melatonin receptors
622:Biological activity
598:In addition to its
575:and its role as an
573:melatonin receptors
50:
8185:α-Alkyltryptamines
8157:-Butanoylmelatonin
8117:6-Methoxymelatonin
8112:6-Hydroxymelatonin
8097:5-Methoxyluzindole
8079:-Acetyltryptamines
7750:Acetryptine (5-AT)
7695:5-Methyltryptamine
7577:5-HTP (oxitriptan)
7206:1,2-Diaminopropane
7007:6-Hydroxymelatonin
6276:Anterior pituitary
6026:(1). Wiley: 5–13.
5280:10.1093/jxb/ern284
5168:Neuroendocrinology
4285:Atkin T, Comai S,
4195:Curr Opin Pulm Med
3963:designeroptics.com
3602:Dewick PM (2002).
3444:10.1093/jxb/eru386
2155:10.1093/jxb/err256
1610:short-day breeders
1594:anterior pituitary
1527:Animals and Humans
1365:dietary supplement
1316:6-hydroxymelatonin
1269:-acetyltransferase
1218:-acetylserotonin.
1169:carbon–carbon bond
1076:
998:-methyltransferase
971:-acetyltransferase
913:protein catabolism
886:
728:
490:Infobox references
255:200-797-7200-797-7
48:
8827:
8826:
8629:Related compounds
8514:tetrahydroharmine
8327:αET (etryptamine)
8149:-Acetyltryptamine
8107:6-Fluoromelatonin
8102:6-Chloromelatonin
8092:2-Phenylmelatonin
7788:
7259:
7258:
7180:Fuel antioxidants
7071:
7022:Alpha-lipoic acid
7015:
7000:Food antioxidants
6959:
6958:
6955:
6954:
6842:
6841:
6662:
6661:
6592:
6591:
6344:
6343:
6102:10.1111/jpi.12025
5641:10.1111/jpi.12253
5450:10.1111/jpi.12253
5180:10.1159/000123198
5153:10.1071/ZO9840803
4820:Endocrine Reviews
4748:10.1159/000237455
4699:(10): 1265–1272.
4462:978-0-8247-5504-1
4348:(16): 1401–1402.
4254:10.1002/phar.1822
4171:10.1111/jpi.12572
3613:978-0-471-49640-3
3484:10.1111/jpi.12026
2877:10.1159/000216538
2787:10.1159/000068571
2679:(21): 3927–3940.
2626:10.1111/jpi.12267
2569:10.1111/jpi.12360
2496:(21): 3863–3881.
2363:10.1111/bph.13536
2250:10.1111/jpi.12267
1937:978-0-323-32602-5
1732:DC3000 infecting
1691:. Also acts as a
1602:long-day breeders
1488:The etymology of
1158:
1151:
1120:
1081:
1056:energy metabolism
1031:
965:by the action of
939:, facilitated by
922:
905:shikimate pathway
900:
865:leptin resistance
850:Weight regulation
786:, a known potent
498:Chemical compound
496:
495:
344:CompTox Dashboard
136:Interactive image
8869:
8844:
8843:
8842:
8835:
8661:7-Aza-5-MeO-DiPT
8646:5-Aza-4-MeO-DiPT
8036:Serotonin (5-HT)
7804:Convolutindole A
7786:
7309:1-Methylpsilocin
7286:
7279:
7272:
7263:
7104:-Acetylserotonin
7069:
7013:
6986:
6979:
6972:
6963:
6720:
6715:Digestive system
6671:
6486:
6425:Thyroid hormones
6201:
6190:
6168:
6161:
6154:
6145:
6140:
6123:
6122:
6104:
6080:
6074:
6073:
6052:
6046:
6045:
6035:
6011:
6005:
6004:
6002:
6000:
5994:
5988:. Archived from
5977:
5968:
5962:
5961:
5925:
5919:
5918:
5902:
5896:
5895:
5884:10.1021/jf010321
5878:(10): 4898–902.
5867:
5861:
5860:
5850:
5840:
5816:
5810:
5809:
5776:(6): 1240–1245.
5761:
5755:
5754:
5744:
5712:
5706:
5705:
5668:
5662:
5661:
5643:
5615:
5606:
5605:
5595:
5569:
5560:
5559:
5519:
5510:
5509:
5469:
5463:
5462:
5452:
5428:
5422:
5421:
5411:
5401:
5377:
5371:
5370:
5342:
5336:
5335:
5307:
5301:
5300:
5282:
5258:
5252:
5251:
5241:
5210:Science Advances
5201:
5192:
5191:
5163:
5157:
5156:
5136:
5130:
5129:
5097:
5088:
5087:
5077:
5053:
5047:
5046:
5036:
5012:
5006:
5005:
4977:
4971:
4970:
4960:
4928:
4922:
4921:
4885:
4879:
4878:
4858:
4852:
4851:
4815:
4809:
4808:
4798:
4789:(3): 1243–1251.
4774:
4768:
4767:
4731:
4725:
4724:
4688:
4682:
4681:
4657:
4651:
4650:
4618:
4609:
4608:
4607:
4603:
4596:
4590:
4589:
4564:(4172): 169–71.
4553:
4547:
4546:
4536:
4512:
4506:
4505:
4473:
4467:
4466:
4446:
4440:
4439:
4429:
4405:
4399:
4398:
4362:
4356:
4335:
4329:
4328:
4310:
4282:
4276:
4275:
4265:
4233:
4227:
4226:
4190:
4184:
4183:
4173:
4149:
4143:
4142:
4140:
4138:
4095:
4086:
4085:
4049:
4043:
4042:
4040:
4038:
4024:
4018:
4017:
3981:
3975:
3974:
3972:
3970:
3965:. 25 August 2021
3955:
3949:
3948:
3938:
3914:
3908:
3907:
3896:
3890:
3889:
3879:
3847:
3841:
3840:
3830:
3798:
3792:
3791:
3747:
3741:
3740:
3704:
3698:
3697:
3665:
3659:
3658:
3648:
3624:
3618:
3617:
3599:
3590:
3589:
3560:
3554:
3553:
3543:
3532:10.1002/iub.1144
3511:
3505:
3504:
3486:
3462:
3456:
3455:
3427:
3416:
3415:
3405:
3373:
3367:
3366:
3356:
3324:
3315:
3314:
3307:
3301:
3300:
3290:
3258:
3252:
3251:
3215:
3209:
3208:
3172:
3166:
3165:
3145:
3139:
3138:
3118:
3112:
3111:
3075:
3069:
3068:
3040:
3034:
3033:
3023:
2983:
2974:
2973:
2928:
2922:
2921:
2905:
2899:
2898:
2888:
2856:
2850:
2849:
2813:
2807:
2806:
2775:Hormone Research
2770:
2764:
2763:
2753:
2721:
2715:
2714:
2696:
2664:
2651:
2650:
2628:
2604:
2593:
2592:
2571:
2547:
2536:
2535:
2513:
2481:
2470:
2469:
2459:
2449:
2425:
2414:
2413:
2411:
2409:
2395:
2389:
2388:
2374:
2342:
2325:
2324:
2314:
2304:
2280:
2271:
2270:
2252:
2228:
2219:
2218:
2208:
2198:
2174:
2168:
2167:
2157:
2133:
2120:
2119:
2075:
2069:
2068:
2032:
2026:
2025:
1997:
1991:
1990:
1972:
1948:
1942:
1941:
1921:
1915:
1914:
1904:
1878:
1869:
1860:
1859:
1841:
1809:
1783:Escherichia coli
1697:fungal pathogens
1693:growth inhibitor
1688:Diplocarpon mali
1682:Malus prunifolia
1662:oxidative stress
1654:, drought, etc.
1631:brain hemisphere
1385:jet lag disorder
1362:over-the-counter
1291:
1260:(PKA). PKA then
1156:
1149:
1118:
1111:
1110:
1109:
1106:
1079:
1027:
986:-acetylserotonin
963:-acetylserotonin
956:neurotransmitter
920:
898:
737:Circadian rhythm
731:Circadian rhythm
682:oxidative stress
643:binding affinity
630:of two types of
581:oxidative stress
569:circannual cycle
550:sleep-wake cycle
544:secreted in the
510:natural compound
453:
447:
441:
435:
428:Chemical formula
368:
367:
352:
350:
334:
314:
303:
292:
275:
248:
240:
229:
218:
198:
178:
158:
138:
114:
67:
58:
51:
8877:
8876:
8872:
8871:
8870:
8868:
8867:
8866:
8852:
8851:
8850:
8840:
8838:
8830:
8828:
8823:
8641:4-Aza-5-MeO-DPT
8624:
8423:
8370:
8179:
8087:2-Iodomelatonin
8070:
7295:
7290:
7260:
7255:
7224:
7220:Ethylenediamine
7211:2,4-Dimethyl-6-
7175:
7095:-Acetylcysteine
6995:
6990:
6960:
6951:
6921:
6888:
6870:
6838:
6807:
6779:
6741:
6709:
6658:
6630:
6588:
6555:
6512:
6475:
6457:
6441:
6433:
6411:
6395:Adrenal medulla
6388:Androstenedione
6340:
6270:
6247:
6195:
6184:
6177:
6172:
6135:
6132:
6127:
6126:
6082:
6081:
6077:
6054:
6053:
6049:
6013:
6012:
6008:
5998:
5996:
5992:
5975:
5970:
5969:
5965:
5927:
5926:
5922:
5904:
5903:
5899:
5869:
5868:
5864:
5818:
5817:
5813:
5763:
5762:
5758:
5714:
5713:
5709:
5670:
5669:
5665:
5617:
5616:
5609:
5571:
5570:
5563:
5521:
5520:
5513:
5471:
5470:
5466:
5430:
5429:
5425:
5392:(4): 7396–437.
5379:
5378:
5374:
5344:
5343:
5339:
5309:
5308:
5304:
5260:
5259:
5255:
5216:(9): eaaw6671.
5203:
5202:
5195:
5165:
5164:
5160:
5138:
5137:
5133:
5099:
5098:
5091:
5055:
5054:
5050:
5014:
5013:
5009:
4979:
4978:
4974:
4943:(3): 20190098.
4937:Interface Focus
4930:
4929:
4925:
4887:
4886:
4882:
4860:
4859:
4855:
4817:
4816:
4812:
4776:
4775:
4771:
4733:
4732:
4728:
4690:
4689:
4685:
4659:
4658:
4654:
4620:
4619:
4612:
4605:
4598:
4597:
4593:
4555:
4554:
4550:
4514:
4513:
4509:
4475:
4474:
4470:
4463:
4448:
4447:
4443:
4407:
4406:
4402:
4364:
4363:
4359:
4336:
4332:
4284:
4283:
4279:
4242:Pharmacotherapy
4235:
4234:
4230:
4192:
4191:
4187:
4151:
4150:
4146:
4136:
4134:
4097:
4096:
4089:
4051:
4050:
4046:
4036:
4034:
4032:www.drugbank.ca
4026:
4025:
4021:
3983:
3982:
3978:
3968:
3966:
3957:
3956:
3952:
3916:
3915:
3911:
3898:
3897:
3893:
3849:
3848:
3844:
3813:(16): 6405–12.
3800:
3799:
3795:
3749:
3748:
3744:
3706:
3705:
3701:
3667:
3666:
3662:
3626:
3625:
3621:
3614:
3601:
3600:
3593:
3562:
3561:
3557:
3513:
3512:
3508:
3464:
3463:
3459:
3429:
3428:
3419:
3375:
3374:
3370:
3326:
3325:
3318:
3309:
3308:
3304:
3260:
3259:
3255:
3217:
3216:
3212:
3174:
3173:
3169:
3147:
3146:
3142:
3120:
3119:
3115:
3077:
3076:
3072:
3051:(15): PL271-6.
3042:
3041:
3037:
2985:
2984:
2977:
2930:
2929:
2925:
2907:
2906:
2902:
2858:
2857:
2853:
2815:
2814:
2810:
2772:
2771:
2767:
2723:
2722:
2718:
2666:
2665:
2654:
2606:
2605:
2596:
2549:
2548:
2539:
2483:
2482:
2473:
2427:
2426:
2417:
2407:
2405:
2397:
2396:
2392:
2357:(18): 2702–25.
2344:
2343:
2328:
2282:
2281:
2274:
2230:
2229:
2222:
2176:
2175:
2171:
2135:
2134:
2123:
2077:
2076:
2072:
2034:
2033:
2029:
1999:
1998:
1994:
1950:
1949:
1945:
1938:
1923:
1922:
1918:
1876:
1871:
1870:
1863:
1811:
1810:
1806:
1801:
1792:
1774:
1750:
1670:transgenic rice
1643:
1537:endocrine gland
1529:
1524:
1516:vasoconstrictor
1486:
1474:Richard Wurtman
1463:Yale University
1455:Aaron B. Lerner
1440:
1435:
1429:
1369:sleep disorders
1354:
1348:
1340:
1304:
1286:
1265:arylalkylamine
1244:by the hormone
1238:
1210:then acts as a
1107:
1104:
1103:
1101:
1099:
1068:
1060:domains of life
943:and the enzyme
937:decarboxylation
878:
873:
852:
827:
819:redox reactions
780:synergistically
739:
733:
719:
690:gene expression
666:
658:
624:
608:sleep disorders
534:skin lightening
526:Aaron B. Lerner
499:
492:
487:
456:
450:
444:
438:
430:
416:
413:
408:
407:
396:
393:
392:
389:
383:
382:
371:
353:
346:
337:
317:
304:
278:
258:
221:
201:
181:
161:
141:
128:
117:
104:
90:
82:
44:
37:
17:
12:
11:
5:
8875:
8873:
8865:
8864:
8854:
8853:
8849:
8848:
8825:
8824:
8822:
8821:
8816:
8811:
8806:
8788:
8783:
8778:
8752:
8747:
8742:
8737:
8732:
8727:
8718:
8713:
8708:
8703:
8698:
8693:
8688:
8683:
8678:
8673:
8668:
8663:
8658:
8653:
8648:
8643:
8638:
8632:
8630:
8626:
8625:
8623:
8622:
8584:
8579:
8574:
8569:
8564:
8559:
8554:
8547:tabernanthalog
8521:
8468:
8463:
8449:
8444:
8439:
8433:
8431:
8425:
8424:
8422:
8421:
8416:
8411:
8406:
8401:
8396:
8391:
8386:
8380:
8378:
8372:
8371:
8369:
8368:
8363:
8354:
8349:
8344:
8339:
8334:
8329:
8324:
8311:
8298:
8285:
8280:
8275:
8270:
8265:
8260:
8255:
8250:
8245:
8240:
8235:
8230:
8225:
8220:
8215:
8210:
8205:
8200:
8195:
8189:
8187:
8181:
8180:
8178:
8177:
8172:
8167:
8159:
8151:
8143:
8137:Normelatonin (
8134:
8129:
8124:
8119:
8114:
8109:
8104:
8099:
8094:
8089:
8083:
8081:
8072:
8071:
8069:
8068:
8063:
8058:
8053:
8048:
8043:
8038:
8033:
8028:
8023:
8018:
8013:
8004:
7999:
7994:
7989:
7984:
7979:
7974:
7969:
7961:
7956:
7951:
7946:
7941:
7936:
7931:
7926:
7921:
7916:
7911:
7906:
7901:
7896:
7891:
7886:
7881:
7876:
7871:
7866:
7861:
7856:
7851:
7846:
7841:
7836:
7831:
7826:
7821:
7816:
7811:
7806:
7801:
7796:
7791:
7782:
7777:
7772:
7767:
7762:
7757:
7752:
7747:
7742:
7737:
7732:
7727:
7722:
7717:
7712:
7707:
7702:
7697:
7692:
7687:
7682:
7677:
7672:
7667:
7662:
7657:
7652:
7647:
7642:
7637:
7632:
7627:
7622:
7617:
7612:
7607:
7602:
7589:
7584:
7579:
7574:
7569:
7564:
7559:
7554:
7549:
7544:
7539:
7534:
7529:
7524:
7519:
7514:
7509:
7504:
7499:
7494:
7489:
7484:
7479:
7474:
7469:
7464:
7459:
7454:
7449:
7444:
7439:
7434:
7429:
7424:
7419:
7414:
7409:
7404:
7399:
7397:4-HO-5-MeO-DMT
7394:
7389:
7384:
7379:
7374:
7369:
7364:
7359:
7354:
7349:
7344:
7339:
7326:
7321:
7316:
7311:
7305:
7303:
7297:
7296:
7291:
7289:
7288:
7281:
7274:
7266:
7257:
7256:
7254:
7253:
7248:
7243:
7238:
7232:
7230:
7226:
7225:
7223:
7222:
7217:
7208:
7203:
7194:
7189:
7183:
7181:
7177:
7176:
7174:
7173:
7168:
7162:
7157:
7147:
7137:
7132:
7127:
7122:
7117:
7112:
7107:
7098:
7089:
7084:
7079:
7074:
7066:
7064:Hydroxytyrosol
7061:
7056:
7051:
7046:
7041:
7031:
7025:
7019:
7009:
7003:
7001:
6997:
6996:
6991:
6989:
6988:
6981:
6974:
6966:
6957:
6956:
6953:
6952:
6950:
6949:
6948:
6947:
6942:
6931:
6929:
6923:
6922:
6920:
6919:
6914:
6909:
6904:
6898:
6896:
6890:
6889:
6887:
6886:
6880:
6878:
6872:
6871:
6869:
6868:
6863:
6858:
6852:
6850:
6848:Adipose tissue
6844:
6843:
6840:
6839:
6837:
6836:
6835:
6834:
6829:
6818:
6816:
6809:
6808:
6806:
6805:
6800:
6795:
6793:Enteroglucagon
6789:
6787:
6781:
6780:
6778:
6777:
6772:
6767:
6762:
6757:
6751:
6749:
6743:
6742:
6740:
6739:
6734:
6728:
6726:
6717:
6711:
6710:
6708:
6707:
6702:
6697:
6696:
6695:
6693:Beta thymosins
6690:
6679:
6677:
6668:
6664:
6663:
6660:
6659:
6657:
6656:
6651:
6646:
6640:
6638:
6632:
6631:
6629:
6628:
6623:
6618:
6613:
6608:
6602:
6600:
6594:
6593:
6590:
6589:
6587:
6586:
6581:
6576:
6571:
6565:
6563:
6557:
6556:
6554:
6553:
6548:
6543:
6538:
6533:
6528:
6522:
6520:
6514:
6513:
6511:
6510:
6505:
6500:
6494:
6492:
6483:
6477:
6476:
6474:
6473:
6467:
6465:
6459:
6458:
6456:
6455:
6450:
6445:
6444:
6443:
6439:
6435:
6431:
6421:
6419:
6413:
6412:
6410:
6409:
6408:
6407:
6405:Norepinephrine
6402:
6392:
6391:
6390:
6385:
6380:
6375:
6370:
6365:
6358:Adrenal cortex
6354:
6352:
6346:
6345:
6342:
6341:
6339:
6338:
6333:
6332:
6331:
6326:
6321:
6316:
6311:
6301:
6296:
6291:
6286:
6280:
6278:
6272:
6271:
6269:
6268:
6263:
6257:
6255:
6249:
6248:
6246:
6245:
6240:
6235:
6230:
6225:
6220:
6215:
6209:
6207:
6198:
6187:
6179:
6178:
6173:
6171:
6170:
6163:
6156:
6148:
6142:
6141:
6131:
6130:External links
6128:
6125:
6124:
6075:
6047:
6006:
5963:
5920:
5897:
5862:
5811:
5756:
5727:(5): 717–724.
5707:
5680:(4): 465–478.
5663:
5607:
5561:
5511:
5464:
5423:
5372:
5337:
5302:
5253:
5193:
5158:
5131:
5089:
5048:
5007:
4972:
4923:
4880:
4853:
4810:
4769:
4742:(3): 203–211.
4726:
4683:
4652:
4610:
4591:
4548:
4507:
4468:
4461:
4441:
4400:
4357:
4330:
4301:(2): 197–245.
4289:(April 2018).
4277:
4248:(9): 1028–41.
4228:
4201:(6): 543–548.
4185:
4144:
4110:(4): 489–494.
4087:
4044:
4019:
3992:(8): 1602–12.
3976:
3950:
3929:(5): 2755–61.
3909:
3891:
3842:
3793:
3742:
3715:(10): 756–66.
3699:
3660:
3633:Molecular Cell
3619:
3612:
3591:
3572:(8): 2229–38.
3555:
3506:
3457:
3417:
3368:
3339:(3): 434–443.
3316:
3302:
3253:
3210:
3167:
3140:
3125:(in Russian).
3113:
3086:(2): 189–200.
3070:
3035:
2975:
2923:
2900:
2851:
2808:
2765:
2716:
2652:
2594:
2537:
2471:
2415:
2390:
2326:
2272:
2243:(4): 403–419.
2220:
2169:
2121:
2070:
2027:
1992:
1943:
1936:
1916:
1861:
1824:(4): 472–479.
1803:
1802:
1800:
1797:
1791:
1788:
1773:
1770:
1749:
1746:
1719:seed treatment
1642:
1639:
1528:
1525:
1523:
1520:
1485:
1482:
1439:
1436:
1431:Main article:
1428:
1425:
1350:Main article:
1347:
1344:
1339:
1336:
1303:
1300:
1262:phosphorylates
1246:norepinephrine
1237:
1234:
1097:
1067:
1064:
1045:carbon dioxide
1041:photosynthetic
994:hydroxyindole
990:hydroxyl group
927:by the enzyme
923:-tryptophan's
896:starting with
877:
874:
872:
869:
860:energy balance
851:
848:
826:
823:
735:Main article:
732:
729:
718:
715:
664:
656:
623:
620:
497:
494:
493:
488:
484:standard state
481:
478:
477:
474:
468:
467:
464:
458:
457:
454:
448:
442:
436:
431:
426:
423:
422:
418:
417:
415:
414:
411:
403:
402:
401:
398:
397:
395:
394:
390:
387:
386:
378:
377:
376:
373:
372:
370:
369:
356:
354:
342:
339:
338:
336:
335:
327:
325:
319:
318:
316:
315:
307:
305:
297:
294:
293:
286:
280:
279:
277:
276:
268:
266:
260:
259:
257:
256:
252:
250:
242:
241:
231:
223:
222:
220:
219:
211:
209:
203:
202:
200:
199:
191:
189:
183:
182:
180:
179:
171:
169:
163:
162:
160:
159:
151:
149:
143:
142:
140:
139:
131:
129:
122:
119:
118:
116:
115:
107:
105:
100:
97:
96:
92:
91:
88:
84:
83:
80:
74:
73:
69:
68:
60:
59:
15:
13:
10:
9:
6:
4:
3:
2:
8874:
8863:
8860:
8859:
8857:
8847:
8837:
8833:
8820:
8817:
8815:
8812:
8810:
8807:
8804:
8800:
8796:
8792:
8789:
8787:
8784:
8782:
8779:
8776:
8772:
8768:
8764:
8760:
8756:
8753:
8751:
8748:
8746:
8743:
8741:
8738:
8736:
8733:
8731:
8728:
8726:
8724:
8719:
8717:
8714:
8712:
8709:
8707:
8704:
8702:
8699:
8697:
8694:
8692:
8689:
8687:
8684:
8682:
8679:
8677:
8674:
8672:
8669:
8667:
8664:
8662:
8659:
8657:
8654:
8652:
8649:
8647:
8644:
8642:
8639:
8637:
8636:2-Azapsilocin
8634:
8633:
8631:
8627:
8620:
8616:
8612:
8608:
8604:
8600:
8596:
8592:
8588:
8585:
8583:
8580:
8578:
8575:
8573:
8570:
8568:
8565:
8563:
8560:
8558:
8555:
8552:
8551:tabernanthine
8548:
8544:
8540:
8536:
8532:
8528:
8526:
8522:
8519:
8515:
8511:
8507:
8503:
8499:
8495:
8491:
8487:
8483:
8479:
8475:
8473:
8469:
8467:
8464:
8461:
8457:
8453:
8450:
8448:
8445:
8443:
8440:
8438:
8435:
8434:
8432:
8430:
8426:
8420:
8417:
8415:
8412:
8410:
8407:
8405:
8402:
8400:
8397:
8395:
8392:
8390:
8387:
8385:
8382:
8381:
8379:
8377:
8373:
8367:
8364:
8362:
8360:
8355:
8353:
8350:
8348:
8345:
8343:
8340:
8338:
8335:
8333:
8330:
8328:
8325:
8323:
8321:
8317:
8312:
8310:
8308:
8304:
8299:
8297:
8295:
8291:
8286:
8284:
8281:
8279:
8276:
8274:
8271:
8269:
8266:
8264:
8261:
8259:
8256:
8254:
8251:
8249:
8246:
8244:
8241:
8239:
8236:
8234:
8231:
8229:
8226:
8224:
8221:
8219:
8216:
8214:
8211:
8209:
8206:
8204:
8201:
8199:
8196:
8194:
8191:
8190:
8188:
8186:
8182:
8176:
8173:
8171:
8168:
8166:
8164:
8160:
8158:
8156:
8152:
8150:
8148:
8144:
8142:
8140:
8135:
8133:
8130:
8128:
8125:
8123:
8120:
8118:
8115:
8113:
8110:
8108:
8105:
8103:
8100:
8098:
8095:
8093:
8090:
8088:
8085:
8084:
8082:
8080:
8078:
8073:
8067:
8064:
8062:
8059:
8057:
8054:
8052:
8049:
8047:
8044:
8042:
8039:
8037:
8034:
8032:
8029:
8027:
8024:
8022:
8019:
8017:
8014:
8012:
8010:
8005:
8003:
8000:
7998:
7995:
7993:
7990:
7988:
7985:
7983:
7980:
7978:
7975:
7973:
7970:
7968:
7966:
7962:
7960:
7957:
7955:
7952:
7950:
7947:
7945:
7942:
7940:
7937:
7935:
7932:
7930:
7927:
7925:
7922:
7920:
7917:
7915:
7912:
7910:
7907:
7905:
7902:
7900:
7897:
7895:
7892:
7890:
7887:
7885:
7882:
7880:
7877:
7875:
7872:
7870:
7867:
7865:
7862:
7860:
7857:
7855:
7852:
7850:
7847:
7845:
7842:
7840:
7837:
7835:
7832:
7830:
7827:
7825:
7822:
7820:
7817:
7815:
7812:
7810:
7807:
7805:
7802:
7800:
7797:
7795:
7792:
7790:
7783:
7781:
7778:
7776:
7773:
7771:
7768:
7766:
7763:
7761:
7758:
7756:
7753:
7751:
7748:
7746:
7743:
7741:
7738:
7736:
7733:
7731:
7728:
7726:
7723:
7721:
7718:
7716:
7713:
7711:
7708:
7706:
7703:
7701:
7698:
7696:
7693:
7691:
7688:
7686:
7683:
7681:
7678:
7676:
7675:5-MeO-T-NBOMe
7673:
7671:
7668:
7666:
7663:
7661:
7658:
7656:
7653:
7651:
7648:
7646:
7643:
7641:
7638:
7636:
7633:
7631:
7628:
7626:
7623:
7621:
7618:
7616:
7613:
7611:
7608:
7606:
7603:
7601:
7599:
7595:
7590:
7588:
7587:5-MeO-34MPEMT
7585:
7583:
7580:
7578:
7575:
7573:
7570:
7568:
7565:
7563:
7560:
7558:
7555:
7553:
7550:
7548:
7545:
7543:
7540:
7538:
7535:
7533:
7530:
7528:
7525:
7523:
7520:
7518:
7515:
7513:
7510:
7508:
7505:
7503:
7500:
7498:
7495:
7493:
7490:
7488:
7485:
7483:
7480:
7478:
7475:
7473:
7470:
7468:
7465:
7463:
7460:
7458:
7455:
7453:
7450:
7448:
7445:
7443:
7440:
7438:
7435:
7433:
7430:
7428:
7425:
7423:
7420:
7418:
7415:
7413:
7410:
7408:
7405:
7403:
7400:
7398:
7395:
7393:
7392:4-F-5-MeO-DMT
7390:
7388:
7385:
7383:
7380:
7378:
7375:
7373:
7370:
7368:
7365:
7363:
7360:
7358:
7355:
7353:
7350:
7348:
7345:
7343:
7340:
7338:
7336:
7332:
7327:
7325:
7324:2-Methyl-5-HT
7322:
7320:
7317:
7315:
7312:
7310:
7307:
7306:
7304:
7302:
7298:
7294:
7287:
7282:
7280:
7275:
7273:
7268:
7267:
7264:
7252:
7249:
7247:
7244:
7242:
7239:
7237:
7234:
7233:
7231:
7227:
7221:
7218:
7216:
7214:
7209:
7207:
7204:
7202:
7200:
7195:
7193:
7190:
7188:
7185:
7184:
7182:
7178:
7172:
7169:
7166:
7163:
7161:
7158:
7155:
7151:
7148:
7145:
7141:
7138:
7136:
7133:
7131:
7128:
7126:
7123:
7121:
7118:
7116:
7113:
7111:
7108:
7105:
7103:
7099:
7096:
7094:
7090:
7088:
7085:
7083:
7080:
7078:
7075:
7073:
7067:
7065:
7062:
7060:
7057:
7055:
7052:
7050:
7047:
7045:
7042:
7039:
7035:
7032:
7029:
7028:Ascorbic acid
7026:
7023:
7020:
7017:
7010:
7008:
7005:
7004:
7002:
6998:
6994:
6987:
6982:
6980:
6975:
6973:
6968:
6967:
6964:
6946:
6943:
6941:
6938:
6937:
6936:
6933:
6932:
6930:
6928:
6924:
6918:
6917:Prostaglandin
6915:
6913:
6910:
6908:
6905:
6903:
6900:
6899:
6897:
6895:
6891:
6885:
6882:
6881:
6879:
6877:
6873:
6867:
6864:
6862:
6859:
6857:
6854:
6853:
6851:
6849:
6845:
6833:
6830:
6828:
6825:
6824:
6823:
6820:
6819:
6817:
6814:
6810:
6804:
6801:
6799:
6796:
6794:
6791:
6790:
6788:
6786:
6782:
6776:
6773:
6771:
6768:
6766:
6763:
6761:
6758:
6756:
6753:
6752:
6750:
6748:
6744:
6738:
6735:
6733:
6730:
6729:
6727:
6725:
6721:
6718:
6716:
6712:
6706:
6703:
6701:
6698:
6694:
6691:
6689:
6686:
6685:
6684:
6681:
6680:
6678:
6676:
6672:
6669:
6665:
6655:
6652:
6650:
6647:
6645:
6642:
6641:
6639:
6637:
6633:
6627:
6624:
6622:
6619:
6617:
6614:
6612:
6609:
6607:
6604:
6603:
6601:
6599:
6595:
6585:
6582:
6580:
6577:
6575:
6572:
6570:
6567:
6566:
6564:
6562:
6558:
6552:
6549:
6547:
6544:
6542:
6539:
6537:
6534:
6532:
6529:
6527:
6524:
6523:
6521:
6519:
6515:
6509:
6506:
6504:
6501:
6499:
6496:
6495:
6493:
6491:
6487:
6484:
6482:
6478:
6472:
6469:
6468:
6466:
6464:
6460:
6454:
6451:
6449:
6446:
6442:
6436:
6434:
6428:
6427:
6426:
6423:
6422:
6420:
6418:
6414:
6406:
6403:
6401:
6398:
6397:
6396:
6393:
6389:
6386:
6384:
6381:
6379:
6376:
6374:
6371:
6369:
6366:
6364:
6361:
6360:
6359:
6356:
6355:
6353:
6351:
6347:
6337:
6334:
6330:
6327:
6325:
6322:
6320:
6317:
6315:
6312:
6310:
6307:
6306:
6305:
6302:
6300:
6297:
6295:
6292:
6290:
6287:
6285:
6282:
6281:
6279:
6277:
6273:
6267:
6264:
6262:
6259:
6258:
6256:
6254:
6250:
6244:
6241:
6239:
6236:
6234:
6231:
6229:
6226:
6224:
6221:
6219:
6216:
6214:
6211:
6210:
6208:
6206:
6202:
6199:
6197:
6194:Hypothalamic–
6191:
6188:
6186:
6180:
6176:
6169:
6164:
6162:
6157:
6155:
6150:
6149:
6146:
6138:
6134:
6133:
6129:
6120:
6116:
6112:
6108:
6103:
6098:
6094:
6090:
6086:
6079:
6076:
6071:
6067:
6064:(3): 627–34.
6063:
6059:
6051:
6048:
6043:
6039:
6034:
6029:
6025:
6021:
6017:
6010:
6007:
5991:
5987:
5983:
5982:
5974:
5967:
5964:
5959:
5955:
5951:
5947:
5943:
5939:
5936:(4): 374–80.
5935:
5931:
5924:
5921:
5916:
5912:
5908:
5901:
5898:
5893:
5889:
5885:
5881:
5877:
5873:
5866:
5863:
5858:
5854:
5849:
5844:
5839:
5834:
5830:
5826:
5822:
5815:
5812:
5807:
5803:
5799:
5795:
5791:
5787:
5783:
5779:
5775:
5771:
5767:
5760:
5757:
5752:
5748:
5743:
5738:
5734:
5730:
5726:
5722:
5718:
5711:
5708:
5703:
5699:
5695:
5691:
5687:
5683:
5679:
5675:
5667:
5664:
5659:
5655:
5651:
5647:
5642:
5637:
5633:
5629:
5625:
5621:
5614:
5612:
5608:
5603:
5599:
5594:
5589:
5585:
5581:
5580:
5575:
5568:
5566:
5562:
5557:
5553:
5549:
5545:
5541:
5537:
5533:
5529:
5525:
5518:
5516:
5512:
5507:
5503:
5499:
5495:
5491:
5487:
5483:
5479:
5475:
5468:
5465:
5460:
5456:
5451:
5446:
5443:(2): 133–50.
5442:
5438:
5434:
5427:
5424:
5419:
5415:
5410:
5405:
5400:
5395:
5391:
5387:
5383:
5376:
5373:
5368:
5364:
5360:
5356:
5352:
5348:
5341:
5338:
5333:
5329:
5325:
5321:
5317:
5313:
5306:
5303:
5298:
5294:
5290:
5286:
5281:
5276:
5272:
5268:
5264:
5257:
5254:
5249:
5245:
5240:
5235:
5231:
5227:
5223:
5219:
5215:
5211:
5207:
5200:
5198:
5194:
5189:
5185:
5181:
5177:
5173:
5169:
5162:
5159:
5154:
5150:
5147:(6): 803–09.
5146:
5142:
5135:
5132:
5128:
5123:
5119:
5115:
5111:
5107:
5103:
5096:
5094:
5090:
5085:
5081:
5076:
5071:
5067:
5063:
5059:
5052:
5049:
5044:
5040:
5035:
5030:
5026:
5022:
5018:
5011:
5008:
5003:
4999:
4995:
4991:
4987:
4983:
4976:
4973:
4968:
4964:
4959:
4954:
4950:
4946:
4942:
4938:
4934:
4927:
4924:
4919:
4915:
4911:
4907:
4903:
4899:
4895:
4891:
4884:
4881:
4876:
4872:
4868:
4864:
4857:
4854:
4849:
4845:
4841:
4837:
4833:
4829:
4826:(2): 151–80.
4825:
4821:
4814:
4811:
4806:
4802:
4797:
4792:
4788:
4784:
4780:
4773:
4770:
4765:
4761:
4757:
4753:
4749:
4745:
4741:
4737:
4730:
4727:
4722:
4718:
4714:
4710:
4706:
4702:
4698:
4694:
4687:
4684:
4679:
4675:
4671:
4667:
4663:
4656:
4653:
4648:
4644:
4640:
4636:
4632:
4628:
4624:
4617:
4615:
4611:
4601:
4595:
4592:
4587:
4583:
4579:
4575:
4571:
4567:
4563:
4559:
4552:
4549:
4544:
4540:
4535:
4530:
4527:(7): 1992–7.
4526:
4522:
4518:
4511:
4508:
4503:
4499:
4495:
4491:
4488:(1): 206–24.
4487:
4483:
4479:
4472:
4469:
4464:
4458:
4454:
4453:
4445:
4442:
4437:
4433:
4428:
4423:
4420:(5): 454–60.
4419:
4415:
4411:
4404:
4401:
4396:
4392:
4388:
4384:
4380:
4376:
4373:(4): 175–86.
4372:
4368:
4361:
4358:
4355:
4351:
4347:
4343:
4340:
4334:
4331:
4326:
4322:
4318:
4314:
4309:
4304:
4300:
4296:
4295:Pharmacol Rev
4292:
4288:
4281:
4278:
4273:
4269:
4264:
4259:
4255:
4251:
4247:
4243:
4239:
4232:
4229:
4224:
4220:
4216:
4212:
4208:
4204:
4200:
4196:
4189:
4186:
4181:
4177:
4172:
4167:
4164:(1): e12572.
4163:
4159:
4155:
4148:
4145:
4133:
4129:
4125:
4121:
4117:
4113:
4109:
4105:
4101:
4094:
4092:
4088:
4083:
4079:
4075:
4071:
4067:
4063:
4059:
4055:
4048:
4045:
4033:
4029:
4023:
4020:
4015:
4011:
4007:
4003:
3999:
3995:
3991:
3987:
3980:
3977:
3964:
3960:
3954:
3951:
3946:
3942:
3937:
3932:
3928:
3924:
3920:
3913:
3910:
3905:
3901:
3895:
3892:
3887:
3883:
3878:
3873:
3869:
3865:
3861:
3857:
3853:
3846:
3843:
3838:
3834:
3829:
3824:
3820:
3816:
3812:
3808:
3804:
3797:
3794:
3789:
3785:
3781:
3777:
3773:
3769:
3765:
3761:
3758:(1): 372–83.
3757:
3753:
3746:
3743:
3738:
3734:
3730:
3726:
3722:
3718:
3714:
3710:
3703:
3700:
3695:
3691:
3687:
3683:
3680:(8): 715–27.
3679:
3675:
3671:
3664:
3661:
3656:
3652:
3647:
3642:
3638:
3634:
3630:
3623:
3620:
3615:
3609:
3605:
3598:
3596:
3592:
3587:
3583:
3579:
3575:
3571:
3567:
3559:
3556:
3551:
3547:
3542:
3537:
3533:
3529:
3525:
3521:
3517:
3510:
3507:
3502:
3498:
3494:
3490:
3485:
3480:
3477:(2): 127–38.
3476:
3472:
3468:
3461:
3458:
3453:
3449:
3445:
3441:
3438:(3): 627–46.
3437:
3433:
3426:
3424:
3422:
3418:
3413:
3409:
3404:
3399:
3395:
3391:
3387:
3383:
3379:
3372:
3369:
3364:
3360:
3355:
3350:
3346:
3342:
3338:
3334:
3330:
3323:
3321:
3317:
3312:
3306:
3303:
3298:
3294:
3289:
3284:
3280:
3276:
3273:(2): 93–100.
3272:
3268:
3264:
3257:
3254:
3249:
3245:
3241:
3237:
3233:
3229:
3225:
3221:
3214:
3211:
3206:
3202:
3198:
3194:
3190:
3186:
3183:(3): 467–76.
3182:
3178:
3171:
3168:
3163:
3159:
3156:(5): 423–31.
3155:
3151:
3144:
3141:
3136:
3132:
3128:
3124:
3117:
3114:
3109:
3105:
3101:
3097:
3093:
3089:
3085:
3081:
3074:
3071:
3066:
3062:
3058:
3054:
3050:
3046:
3045:Life Sciences
3039:
3036:
3031:
3027:
3022:
3017:
3013:
3009:
3005:
3001:
2997:
2993:
2989:
2982:
2980:
2976:
2971:
2967:
2963:
2959:
2955:
2951:
2947:
2943:
2940:(1): 419–20.
2939:
2935:
2927:
2924:
2919:
2915:
2911:
2904:
2901:
2896:
2892:
2887:
2882:
2878:
2874:
2871:(4): 276–84.
2870:
2866:
2862:
2855:
2852:
2847:
2843:
2839:
2835:
2831:
2827:
2824:(4): 379–88.
2823:
2819:
2812:
2809:
2804:
2800:
2796:
2792:
2788:
2784:
2780:
2776:
2769:
2766:
2761:
2757:
2752:
2747:
2743:
2739:
2736:(2): 135–41.
2735:
2731:
2727:
2720:
2717:
2712:
2708:
2704:
2700:
2695:
2690:
2686:
2682:
2678:
2674:
2670:
2663:
2661:
2659:
2657:
2653:
2649:
2644:
2640:
2636:
2632:
2627:
2622:
2619:(4): 403–19.
2618:
2614:
2610:
2603:
2601:
2599:
2595:
2591:
2587:
2583:
2579:
2575:
2570:
2565:
2562:(3): 253–78.
2561:
2557:
2553:
2546:
2544:
2542:
2538:
2534:
2529:
2525:
2521:
2517:
2512:
2507:
2503:
2499:
2495:
2491:
2487:
2480:
2478:
2476:
2472:
2467:
2463:
2458:
2453:
2448:
2443:
2439:
2435:
2431:
2424:
2422:
2420:
2416:
2404:
2400:
2394:
2391:
2387:
2382:
2378:
2373:
2368:
2364:
2360:
2356:
2352:
2348:
2341:
2339:
2337:
2335:
2333:
2331:
2327:
2322:
2318:
2313:
2308:
2303:
2298:
2294:
2290:
2286:
2279:
2277:
2273:
2268:
2264:
2260:
2256:
2251:
2246:
2242:
2238:
2234:
2227:
2225:
2221:
2216:
2212:
2207:
2202:
2197:
2192:
2188:
2184:
2180:
2173:
2170:
2165:
2161:
2156:
2151:
2148:(2): 577–97.
2147:
2143:
2139:
2132:
2130:
2128:
2126:
2122:
2117:
2113:
2109:
2105:
2101:
2097:
2093:
2089:
2086:(1): 200–15.
2085:
2081:
2074:
2071:
2066:
2062:
2058:
2054:
2050:
2046:
2043:(2): 119–30.
2042:
2038:
2031:
2028:
2023:
2019:
2015:
2011:
2007:
2003:
1996:
1993:
1988:
1984:
1980:
1976:
1971:
1966:
1963:(5): 835–45.
1962:
1958:
1954:
1947:
1944:
1939:
1933:
1929:
1928:
1920:
1917:
1912:
1908:
1903:
1898:
1894:
1890:
1886:
1882:
1875:
1868:
1866:
1862:
1857:
1853:
1849:
1845:
1840:
1835:
1831:
1827:
1823:
1819:
1815:
1808:
1805:
1798:
1796:
1790:Food products
1789:
1787:
1785:
1784:
1778:
1771:
1769:
1767:
1766:
1761:
1757:
1756:
1747:
1745:
1743:
1742:
1736:
1735:
1731:
1726:
1725:
1724:Lupinus albus
1720:
1716:
1715:
1710:
1709:
1704:
1703:
1698:
1694:
1690:
1689:
1684:
1683:
1678:
1673:
1671:
1667:
1663:
1659:
1655:
1653:
1652:soil salinity
1647:
1640:
1638:
1636:
1632:
1629:pattern (one
1628:
1624:
1620:
1618:
1613:
1611:
1607:
1603:
1599:
1595:
1591:
1587:
1583:
1579:
1574:
1570:
1569:photoperiodic
1564:
1560:
1558:
1554:
1550:
1547:from retinal
1546:
1542:
1538:
1534:
1526:
1521:
1519:
1517:
1513:
1512:vascular tone
1509:
1505:
1501:
1497:
1496:
1491:
1483:
1481:
1479:
1475:
1470:
1468:
1467:skin diseases
1464:
1460:
1456:
1451:
1449:
1446:
1437:
1434:
1426:
1424:
1421:
1417:
1413:
1408:
1406:
1402:
1398:
1394:
1390:
1386:
1382:
1378:
1374:
1370:
1366:
1363:
1359:
1353:
1345:
1343:
1337:
1335:
1333:
1329:
1325:
1321:
1317:
1313:
1309:
1306:Melatonin is
1301:
1299:
1296:
1290:
1287:460–480
1283:
1281:
1277:
1274:
1270:
1268:
1263:
1259:
1255:
1251:
1247:
1243:
1235:
1233:
1231:
1229:
1224:
1219:
1217:
1213:
1212:leaving group
1209:
1205:
1201:
1197:
1193:
1189:
1185:
1180:
1178:
1177:pyridine ring
1174:
1170:
1166:
1162:
1153:
1152:-tryptophan.
1147:
1143:
1139:
1135:
1131:
1126:
1122:
1121:-tryptophan.
1115:
1095:
1090:
1088:
1085:
1072:
1065:
1063:
1061:
1057:
1053:
1048:
1046:
1042:
1038:
1034:
1030:
1025:
1021:
1017:
1012:
1010:
1006:
1004:
999:
997:
991:
987:
985:
980:
976:
972:
970:
964:
962:
957:
952:
950:
946:
942:
938:
934:
930:
926:
918:
917:hydroxylation
914:
910:
906:
902:
895:
891:
882:
875:
870:
868:
866:
861:
857:
849:
847:
845:
841:
837:
832:
831:immune system
825:Immune system
824:
822:
820:
816:
812:
808:
803:
801:
797:
792:
789:
785:
781:
777:
773:
769:
765:
761:
757:
752:
750:
745:
738:
730:
723:
716:
714:
711:
707:
703:
699:
695:
691:
687:
686:free radicals
683:
679:
675:
670:
668:
667:alpha subunit
660:
659:alpha subunit
652:
648:
644:
641:
637:
633:
629:
621:
619:
617:
613:
609:
605:
601:
596:
594:
590:
586:
582:
578:
574:
570:
566:
562:
561:synchronizing
557:
555:
551:
547:
543:
539:
535:
531:
527:
523:
519:
515:
511:
507:
503:
491:
485:
479:
475:
473:
472:Melting point
470:
469:
465:
463:
460:
459:
432:
429:
425:
424:
419:
410:
406:
399:
385:
381:
374:
366:
362:
361:DTXSID1022421
358:
357:
355:
345:
341:
340:
333:
329:
328:
326:
324:
321:
320:
313:
309:
308:
306:
300:
296:
295:
291:
287:
285:
282:
281:
274:
270:
269:
267:
265:
262:
261:
254:
253:
251:
249:
244:
243:
239:
235:
232:
230:
228:ECHA InfoCard
225:
224:
217:
213:
212:
210:
208:
205:
204:
197:
193:
192:
190:
188:
185:
184:
177:
173:
172:
170:
168:
165:
164:
157:
153:
152:
150:
148:
145:
144:
137:
133:
132:
130:
126:
121:
120:
113:
109:
108:
106:
103:
99:
98:
93:
85:
79:
75:
70:
66:
61:
57:
52:
46:
42:
36:
34:
29:
27:
22:
8722:
8706:Latrepirdine
8619:rescinnamine
8603:corynanthine
8557:Metralindole
8524:
8478:β-carbolines
8471:
8456:lysergamides
8447:Cyclic 3-OHM
8419:Zolmitriptan
8399:Frovatriptan
8358:
8319:
8315:
8306:
8302:
8296:-methyl-αMT)
8293:
8289:
8273:7-Methyl-αET
8268:7-Chloro-αMT
8263:6-Fluoro-αMT
8258:5-Methyl-αET
8233:5-Fluoro-αMT
8228:5-Fluoro-αET
8223:5-Ethoxy-αMT
8218:5-Chloro-αMT
8170:Piromelatine
8162:
8154:
8146:
8138:
8131:
8076:
8008:
8007:Psilacetin (
7964:
7899:Idalopirdine
7789:-tryptophan)
7745:7-Methyl-DMT
7740:6-Fluoro-DMT
7725:5,6-MDO-MiPT
7715:5,6-MDO-DiPT
7710:5,6-MeO-MiPT
7690:5-Methyl-DMT
7670:5-MeO-NBpBrT
7597:
7593:
7567:5-Fluoro-MET
7562:5-Fluoro-EPT
7557:5-Fluoro-DMT
7552:5-Fluoro-DET
7542:5-Ethoxy-DMT
7537:5-Chloro-DMT
7517:4,5-MDO-DiPT
7334:
7330:
7236:Folin method
7229:Measurements
7215:-butylphenol
7212:
7201:-butylphenol
7198:
7167:(coenzyme Q)
7150:Tocotrienols
7101:
7092:
7081:
6993:Antioxidants
6700:Thymopoietin
6643:
6636:Pineal gland
6621:Somatostatin
6584:Progesterone
6531:Progesterone
6498:Testosterone
6481:Gonadal axis
6453:Thyroid axis
6350:Adrenal axis
6205:Hypothalamus
6139:. Chemwatch.
6095:(1): 58–64.
6092:
6088:
6078:
6061:
6057:
6050:
6023:
6019:
6009:
5997:. Retrieved
5990:the original
5985:
5979:
5966:
5933:
5929:
5923:
5917:(4): 229–36.
5914:
5910:
5900:
5875:
5871:
5865:
5828:
5824:
5814:
5773:
5769:
5759:
5724:
5720:
5710:
5677:
5673:
5666:
5627:
5623:
5583:
5577:
5527:
5523:
5477:
5473:
5467:
5440:
5436:
5426:
5389:
5385:
5375:
5353:(9): 920–4.
5350:
5346:
5340:
5318:(1): 55–67.
5315:
5311:
5305:
5273:(1): 57–69.
5270:
5266:
5256:
5213:
5209:
5171:
5167:
5161:
5144:
5140:
5134:
5125:
5108:(1): 25–39.
5105:
5101:
5065:
5061:
5051:
5024:
5020:
5010:
4985:
4975:
4940:
4936:
4926:
4893:
4889:
4883:
4866:
4862:
4856:
4823:
4819:
4813:
4786:
4782:
4772:
4739:
4735:
4729:
4696:
4692:
4686:
4672:(1): 37–49.
4669:
4665:
4655:
4633:(10): 2587.
4630:
4626:
4594:
4561:
4557:
4551:
4524:
4520:
4510:
4485:
4481:
4471:
4451:
4444:
4417:
4413:
4403:
4370:
4366:
4360:
4345:
4341:
4333:
4298:
4294:
4280:
4245:
4241:
4231:
4198:
4194:
4188:
4161:
4157:
4147:
4135:. Retrieved
4107:
4103:
4057:
4053:
4047:
4035:. Retrieved
4031:
4022:
3989:
3985:
3979:
3967:. Retrieved
3962:
3953:
3926:
3922:
3912:
3903:
3894:
3862:(1): A22-7.
3859:
3855:
3845:
3810:
3806:
3796:
3755:
3751:
3745:
3712:
3708:
3702:
3677:
3673:
3663:
3639:(1): 23–32.
3636:
3632:
3622:
3603:
3569:
3566:Biochemistry
3565:
3558:
3526:(4): 350–7.
3523:
3519:
3509:
3474:
3470:
3460:
3435:
3431:
3385:
3381:
3371:
3336:
3332:
3305:
3270:
3266:
3256:
3223:
3219:
3213:
3180:
3176:
3170:
3153:
3149:
3143:
3129:(5): 73–80.
3126:
3122:
3116:
3083:
3079:
3073:
3048:
3044:
3038:
2998:(3): 89–95.
2995:
2991:
2937:
2933:
2926:
2917:
2913:
2903:
2868:
2864:
2854:
2821:
2817:
2811:
2781:(2): 66–72.
2778:
2774:
2768:
2733:
2729:
2719:
2676:
2672:
2646:
2616:
2612:
2589:
2559:
2555:
2531:
2493:
2489:
2437:
2433:
2406:. Retrieved
2402:
2393:
2384:
2354:
2350:
2292:
2288:
2240:
2236:
2186:
2182:
2172:
2145:
2141:
2083:
2079:
2073:
2040:
2036:
2030:
2008:(8): 412–9.
2005:
2001:
1995:
1960:
1956:
1946:
1926:
1919:
1884:
1880:
1821:
1817:
1807:
1793:
1781:
1779:
1775:
1763:
1760:Novo Nordisk
1753:
1751:
1740:
1733:
1729:
1722:
1712:
1706:
1700:
1686:
1680:
1674:
1665:
1656:
1648:
1644:
1621:
1614:
1565:
1561:
1533:pineal gland
1530:
1503:
1499:
1493:
1489:
1487:
1471:
1452:
1448:melanophores
1441:
1409:
1375:and various
1371:, including
1355:
1341:
1305:
1284:
1266:
1239:
1227:
1222:
1220:
1215:
1183:
1181:
1154:
1127:
1123:
1091:
1077:
1052:chloroplasts
1049:
1013:
1002:
995:
983:
973:, utilizing
968:
960:
953:
890:biosynthesis
887:
876:Biosynthesis
871:Biochemistry
853:
828:
813:(AFMK), and
804:
800:blood plasma
793:
776:nitric oxide
770:(O2−•), and
762:, including
753:
740:
678:mitochondria
671:
628:full agonist
625:
614:and various
610:, including
597:
585:mitochondria
558:
538:common frogs
530:pineal gland
516:, including
501:
500:
95:Identifiers
87:Other names
45:
35:(video game)
32:
25:
8803:naratriptan
8781:Tepirindole
8615:deserpidine
8595:rauwolscine
8543:noribogaine
8414:Sumatriptan
8409:Rizatriptan
8389:Donitriptan
8384:Almotriptan
8066:Z2876442907
8041:Solypertine
7949:Milipertine
7919:Lespedamine
7720:5,6-MDO-DMT
7700:5-MT-NB3OMe
7665:5-MeO-pyr-T
7582:5-MeO-2-TMT
7547:5-Ethyl-DMT
7527:5-Bromo-DMT
7512:4,5-MDO-DMT
7342:4,5-DHP-DMT
7301:Tryptamines
7293:Tryptamines
7140:Tocopherols
7125:Resveratrol
7110:Oleocanthal
7059:Glutathione
7054:Polyphenols
7034:Carotenoids
7030:(vitamin C)
6884:Osteocalcin
6861:Adiponectin
6688:Thymosin α1
6463:Parathyroid
6363:Aldosterone
6266:Vasopressin
6137:"Melatonin"
5825:Metabolites
5174:(1): 43–6.
5068:(1): 1–13.
4896:(1): 1–25.
4060:(1): 1–10.
4028:"Melatonin"
3709:Cephalalgia
3388:(1): 5–17.
1721:, protects
1578:mynah birds
1459:dermatology
1405:agomelatine
1401:tasimelteon
1338:Measurement
1308:metabolized
1276:proteolysis
1273:proteasomal
1192:deprotonate
1173:protonation
1146:aromaticity
1138:carbocation
1136:to yield a
1134:double bond
979:methylation
947:, yielding
925:indole ring
901:-tryptophan
674:antioxidant
577:antioxidant
554:vertebrates
506:indoleamine
421:Properties
234:100.000.725
156:CHEBI:16796
81:N-acetamide
8795:avitriptan
8786:Tetrindole
8763:5-MeO-DiBF
8745:Sertindole
8725:)-69 (3IQ)
8716:Pirlindole
8691:EMD-386088
8607:ajmalicine
8599:spegatrine
8577:PNU-181731
8518:tryptoline
8466:Flucindole
8442:Ciclindole
8437:Bay R 1531
8394:Eletriptan
8253:5-MeO-MPMI
8243:5-MeO-αET
8238:5-iPrO-αMT
8061:Yuremamine
8056:Tryptophan
8051:Tryptamine
7997:Oxypertine
7909:Indorenate
7809:CP-132,484
7655:5-MeO-MiPT
7645:5-MeO-MALT
7635:5-MeO-EiPT
7620:5-MeO-DiPT
7605:5-MeO-DALT
7502:4-MeO-MiPT
7492:4-MeO-DiPT
7487:4-HO-pyr-T
7452:4-HO-McPeT
7387:4-AcO-MiPT
7372:4-AcO-MALT
7357:4-AcO-DiPT
7347:4-AcO-DALT
7165:Ubiquinone
7130:Selegiline
7120:Rasagiline
7115:Oleuropein
7087:Mofegiline
7077:Ladostigil
7072:-carnitine
7016:-carnitine
6912:Calcitriol
6798:Peptide YY
6448:Calcitonin
6400:Adrenaline
6329:Lipotropin
6324:Endorphins
5634:: 133–50.
5534:: 789–97.
5484:: 258–63.
5312:Toxicology
5027:: 114601.
4482:J Exp Zool
4137:25 January
4037:29 January
3711:(Review).
3520:IUBMB Life
3226:: 113598.
2189:(2): 509.
1799:References
1739:infecting
1702:Alternaria
1699:including
1677:resistance
1535:, a small
1522:Occurrence
1302:Metabolism
1236:Regulation
1208:coenzyme A
1182:Serotonin
975:acetyl-CoA
967:serotonin
909:chorismate
788:lipophilic
768:superoxide
600:endogenous
589:organelles
522:eukaryotes
462:Molar mass
332:JL5DK93RCL
187:ChemSpider
123:3D model (
102:CAS Number
78:IUPAC name
49:Melatonin
8862:Melatonin
8814:VU6067416
8799:LY-334370
8771:dimemebfe
8740:RU-24,969
8735:Ro60-0213
8730:Ro60-0175
8711:LY-367265
8681:BRL-54443
8676:AL-38022A
8666:AAZ-A-154
8611:reserpine
8591:yohimbine
8587:Yohimbans
8572:PNU-22394
8567:PHA-57378
8539:ibogamine
8527:alkaloids
8494:harmaline
8482:6-MeO-THH
8474:alkaloids
8452:Ergolines
8352:CP-135807
8347:BW-723C86
8248:5-MeO-αMT
8132:Melatonin
8127:Luzindole
7680:5-MeS-DMT
7660:5-MeO-NMT
7650:5-MeO-MET
7640:5-MeO-EPT
7630:5-MeO-DPT
7625:5-MeO-DMT
7615:5-MeO-DET
7610:5-MeO-DBT
7572:5-HO-DiPT
7507:4-PrO-DMT
7497:4-MeO-DMT
7482:4-HO-PiPT
7472:4-HO-NALT
7467:4-HO-MsBT
7457:4-HO-MiPT
7447:4-HO-McPT
7437:4-HO-MALT
7427:4-HO-DSBT
7417:4-HO-DiPT
7402:4-HO-DALT
7382:4-AcO-DPT
7377:4-AcO-MET
7367:4-AcO-NMT
7362:4-AcO-EPT
7352:4-AcO-DET
7171:Uric acid
7154:vitamin E
7144:vitamin E
7082:Melatonin
7049:Edaravone
7038:vitamin A
6683:Thymosins
6644:Melatonin
6526:Estradiol
6373:Cortisone
6299:Prolactin
6196:pituitary
6183:Endocrine
5831:(1): 72.
5806:219331624
5790:2161-5063
5702:220657247
5386:Molecules
5347:Nutrition
5043:0278-6915
4994:1899-1505
4756:1018-2438
4713:0006-2952
4647:0002-7863
4014:145296760
3969:26 August
3501:206140413
3248:237603177
3080:Endocrine
2914:Endocr. J
2183:Molecules
2037:Endocrine
1887:: 10–22.
1660:-induced
1658:Herbicide
1635:sirenians
1623:Cetaceans
1592:from the
1553:nocturnal
1508:serotonin
1490:melatonin
1484:Etymology
1480:in 1995.
1445:epidermal
1438:Discovery
1397:ramelteon
1395:, namely
1196:lone pair
1188:histidine
1142:1,2-shift
1066:Mechanism
1039:, and in
949:serotonin
784:vitamin E
640:picomolar
514:organisms
502:Melatonin
290:Melatonin
247:EC Number
33:Melatonin
26:Melatonin
8856:Category
8846:Medicine
8809:VER-3323
8791:Triptans
8686:CP-94253
8671:AL-34662
8582:RU-28306
8535:ibogaine
8510:pinoline
8498:harmalol
8404:L-694247
8376:Triptans
8357:IPAP (α,
8213:4-Me-αMT
8208:4-Me-αET
8198:4-HO-αMT
8031:RS134-49
7884:FGIN-143
7879:FGIN-127
7592:5-MeO-7,
7477:4-HO-NMT
7462:4-HO-MPT
7442:4-HO-MET
7432:4-HO-EPT
7422:4-HO-DPT
7412:4-HO-DET
7407:4-HO-DBT
7319:2-Me-DET
7314:2-HO-NMT
7135:Selenium
7044:Curcumin
6876:Skeleton
6866:Resistin
6765:Secretin
6747:Duodenum
6705:Thymulin
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5950:21342247
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2065:46984486
2057:16217125
2022:15992934
1987:18050554
1979:17298593
1911:28648359
1856:52954755
1848:30304113
1839:10118741
1772:Bacteria
1714:Fusarium
1708:Botrytis
1685:against
1598:breeding
1573:coloring
1379:such as
1373:insomnia
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1094:electron
1084:cofactor
1020:protists
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