675:
574:
477:
418:
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234:
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33:
214:, a key plant ingredient in the preparation of ayahuasca; a sacramental beverage from the Amazon. This isolated chemical was so named because of the reported effects of ayahuasca among the indigenous users, including: collective contact with and/or visions of jaguars, snakes, and jeweled birds, and ancestral spirits; the ability to see future events; and as the name suggests,
725:
650:
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368:(October 2015). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.
180:
states of consciousness, the recipes vary greatly and no single combination is common. Peganum harmala, normally consumed as a tea or used as an incense, is mentioned in classical
Persian literature both as a sacred sacrament and as a medicine. The harmala alkaloids are not especially psychedelic, even at higher dosages, when
179:
vine, the key plant ingredient in the sacramental beverage ayahuasca, in concentrations that range between 0.31 and 8.43% for harmine, 0.03–0.83% for harmaline and 0.05–2.94% for tetrahydroharmine. Although other psychoactive plants are occasionally added to ayahuasca to achieve visionary
371:
Exceptions are made when in herbs, or preparations, for therapeutic use such as: (a) containing 0.1 per cent or less of harmala alkaloids; or (b) in divided preparations containing 2 mg or less of harmala alkaloids per recommended daily dose.
293:
when either smoked/vaporized, or taken orally as an extract or as a tea. Reports are scarce, but generally users experience more intense cannabis-like effects, as well as mild psychedelic effects such as hallucinations,
286:(ET) when injected to animals. Rats being treated with harmaline exhibit severe tremors after 5–7 minutes. Individuals diagnosed with essential tremor have been found to have elevated blood levels of harmala alkaloids.
218:
communication among tribal members. It was assumed to be a newly discovered chemical at the time, however, it was soon realized that telepathine was already more widely known as "harmine" from its previous discovery in
174:
in concentrations of roughly 3%, though tests have documented anywhere from 2–7% or even higher, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the
365:
2629:
1734:
1234:
Jahaniani F, Ebrahimi SA, Rahbar-Roshandel N, Mahmoudian M (July 2005). "Xanthomicrol is the main cytotoxic component of
Dracocephalum kotschyii and a potential anti-cancer agent".
896:
Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H (March 2010). "beta-Carboline alkaloids in
Peganum harmala and inhibition of human monoamine oxidase (MAO)".
4119:
1620:
1701:
2622:
104:, and their derivatives, which have similar chemical structures, hence the name "harmala alkaloids". These alkaloids are of interest for their use in Amazonian
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780:
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4369:
4024:
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263:(DMT) and other tryptamines; while not generally used as a hallucinogen alone, there are reports of such use. In high doses, it acts as
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4028:
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1346:
1296:"Monoamine Oxidase-A Inhibition and Associated Antioxidant Activity in Plant Extracts with Potential Antidepressant Actions"
5050:
4985:
3880:
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1511:
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inhibitors. Both MAO-A and MAO-B break down tyramine, but large doses of harmala alkaloids begin to affect MAO-B as well.
5078:
4101:
4000:
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has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible inhibitors of
5428:
3850:
3388:
2590:
2173:
2106:
775:
674:
256:
51:
1379:
Herraiz T (November 2004). "Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke".
4899:
5237:
4701:
3569:
3564:
3249:
2877:
2837:
2815:
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1936:
1844:
833:"Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee"
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251:. These three extractions indicate that the middle one has a higher concentration of the two compounds.
5438:
5423:
5015:
1422:
Ayoub Mikdad T., Rashan L.J. (1991). "Isoharmine, a β-carboline alkaloid from
Peganum harmala seeds".
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4047:
4004:
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3305:
2533:
2448:
1431:
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analyses of
Banisteriopsis caapi and Psychotria viridis Journal of Psychoactive Drugs 37(2): 145-150.
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1327:
1259:
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Louis ED, Zheng W, Jurewicz EC, Watner D, Chen J, Factor-Litvak P, Parides M (December 2002).
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1016:
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leukemic cell lines. This action might explain the previously observed cytotoxic effect of
321:-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not
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1991:
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1531:
476:
244:
2607:
1459:
1201:"The scientific investigation of Ayahuasca: a review of past and current research"
1174:
1150:"Syrian Rue & Cannabis - Erowid Exp - 'Intense, Terrifying and Unconcerning'"
1149:
17:
5580:
5392:
5372:
5320:
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2006:
1996:
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32:
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4279:
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2001:
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1813:
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1714:
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1686:
1638:
1610:
1605:
1600:
1585:
1575:
1392:
1045:"Telepathine (ayahuasca) and psychic ability: field research in South America"
989:"Banisteriopsis caapi, a Forgotten Potential Therapy for Parkinson's Disease?"
965:
952:
Dhawan K, Dhawan S, Sharma A (September 2004). "Passiflora: a review update".
909:
848:
699:
302:
199:
have been reported variously to give 0.005%, 0.12%, and 0% harmala alkaloids.
189:
181:
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1012:
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5576:
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5512:
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2066:
2031:
2011:
1976:
1932:
1790:
1747:
1719:
1653:
1595:
832:
794:
440:
364:
Harmala alkaloids are considered
Schedule 9 prohibited substances under the
334:
295:
264:
237:
215:
160:
156:
105:
97:
81:
1400:
1331:
1312:
1263:
1135:
1030:
973:
925:
856:
5586:
5463:
5448:
5364:
5359:
5312:
5287:
5275:
5229:
5181:
4808:
4793:
4661:
4656:
4254:
4239:
4219:
4209:
4199:
4189:
4184:
4096:
4091:
3719:
3524:
3428:
3404:
3378:
3331:
3295:
3255:
3197:
3064:
2890:
2855:
2724:
2682:
2194:
2150:
1874:
1859:
1496:
1090:, Erowid Online Texts: TiHKAL #13 HARMALINE, retrieved November 26, 2006.
1044:
495:
318:
120:
101:
47:
724:
5568:
5283:
5279:
5153:
5119:
4952:
4823:
4542:
4537:
3940:
3172:
3081:
3073:
2016:
1004:
917:
764:
649:
381:
241:
93:
85:
987:
Djamshidian A, Bernschneider-Reif S, Poewe W, Lees AJ (January 2016).
619:
123:
that is structurally related to harmaline, and also found in the vine
5596:
5498:
5308:
4769:
4731:
4666:
4631:
4626:
4547:
3335:
2675:
66:
1768:
1621:
531:
1702:
108:, where they are derived from other plants. Harmine, once known as
5527:
5339:
4803:
3709:
3533:
3054:
2687:
232:
184:
visions, alongside vomiting and diarrhea, become the main effect.
1474:) - Dr. Duke's Phytochemical and Ethnobotanical Databases at NAL"
1102:"Elevation of blood beta-carboline alkaloids in essential tremor"
4671:
4641:
4591:
342:
338:
310:
306:
210:
was originally thought to be the active chemical constituent of
55:
4043:
2611:
2496:
2400:
2171:
1930:
1740:
1563:
1543:
1500:
187:
Harmala alkaloids are also found in many other plants, such as
4039:
3459:
1175:"Syrian Rue & Cannabis - Erowid Exp - 'Testing Its Power'"
255:
As mentioned above, some harmala alkaloids can be used as a
3770:
2660:
1801:
883:
Tryptamines i Have Known And Loved: The
Chemistry Continues
1669:
3740:
818:
Neuropathology of Drug
Addictions and Substance Misuse
298:, and increased emotions, especially in large doses.
3881:
3509:
1773:
Tooltip
Serotonin antagonist and reuptake inhibitors
1626:
Tooltip Serotonin–norepinephrine reuptake inhibitors
313:
meaning they do not have nearly as high a risk for "
5406:
5205:
5152:
4961:
4852:
4077:
3949:
3879:
3811:
3802:
3768:
3738:
3688:
3667:
3507:
3457:
3389:
3387:
3314:
3274:
3248:
2772:
2658:
2651:
2358:
2298:
2184:
2143:
2107:
2105:
1947:
1827:
1799:
1766:
1733:
1707:
Tooltip Norepinephrine–dopamine reuptake inhibitors
1700:
1667:
1619:
1561:
1277:
1275:
1273:
3276:
1949:
3813:
2509:
1568:Tooltip Selective serotonin reuptake inhibitors
3690:
3464:Tooltip Phenylethanolamine N-methyltransferase
2793:
1348:Edward J. Massaro, Handbook of Neurotoxicology
4055:
2623:
1512:
1283:https://www.comlaw.gov.au/Details/F2015L01534
938:Callaway JC, Brito GS & Neves ES (2005).
8:
3316:
282:, harmala alkaloids are used as a model for
3775:Tooltip Acetylserotonin O-methyltransferase
2665:Tooltip Aromatic L-amino acid decarboxylase
2543:
2360:
2300:
1806:Tooltip Serotonin modulator and stimulators
781:Reversible inhibitor of monoamine oxidase A
431:reversible inhibitor of monoamine oxidase A
4062:
4048:
4040:
3808:
3685:
3271:
2802:
2783:
2655:
2630:
2616:
2608:
2493:
2397:
2181:
2168:
1944:
1927:
1674:Tooltip Norepinephrine reuptake inhibitors
1558:
1540:
1519:
1505:
1497:
1205:The Heffter Review of Psychedelic Research
609:-carboline. Harmalan occurs in foodstuffs.
54:(MAOIs). These alkaloids are found in the
2774:
1321:
1311:
1199:McKenna DJ, Callaway JC, Grob CS (1998).
1125:
1020:
831:Herraiz T, Chaparro C (18 January 2006).
1460:Tetrahydroharmine entry in TiHKAL • info
333:Isolated harmine was found to exhibit a
31:
3951:
808:
289:Harmala alkaloids interact with smoked
3745:Tooltip Serotonin N-acetyl transferase
259:(MAOI) to facilitate the ingestion of
3886:Tooltip Histamine N-methyltransferase
3514:Tooltip Catechol-O-methyl transferase
1051:. Scarborough, UK. 20 September 2009.
7:
4463:5-Methoxytryptamine (5-MT; mexamine)
993:Movement Disorders Clinical Practice
3394:Tooltip Dopamine beta-monooxygenase
2112:Tooltip Tetracyclic antidepressants
1118:10.1212/01.wnl.0000038385.60538.19
25:
3281:Tooltip Phenylalanine hydroxylase
1954:Tooltip Tricyclic antidepressants
1211:(65–77): 195–223. Archived from
748:
723:
698:
673:
648:
618:
572:
530:
475:
462:4,9-Dihydro-7-methoxy-1-methyl-3
416:
147:(RIMAs). They can stimulate the
4745:-Feruloylserotonin (moschamine)
3818:Tooltip Histidine decarboxylase
1381:Food Additives and Contaminants
1256:10.1016/j.phytochem.2005.04.035
816:Kivell BM, Danielson K (2016).
170:The harmala alkaloids occur in
4900:6,7-Dichloro-2-methylmelatonin
3695:Tooltip Tryptophan hydroxylase
3475:Norepinephrine (noradrenaline)
3409:Norepinephrine (Noradrenaline)
2834:Norepinephrine (noradrenaline)
2798:Tooltip Aldehyde dehydrogenase
1281:Poisons Standard October 2015
39:, commonly known as Syrian Rue
1:
4021:Monoamine reuptake inhibitors
4001:Receptor/signaling modulators
1300:BioMed Research International
1294:Herraiz T, Guillén H (2018).
1049:British Psychological Society
5628:Monoamine oxidase inhibitors
5056:α-Methylserotonin (5-HO-αMT)
4563:Benzotript (4-chlorobenzoyl-
3321:Tooltip Tyrosine hydroxylase
2174:Monoamine oxidase inhibitors
1444:10.1016/0031-9422(91)85312-N
954:Journal of Ethnopharmacology
898:Food and Chemical Toxicology
695:-carboline-1-carboxylic acid
305:, harmine and harmaline are
52:monoamine oxidase inhibitors
4789:-acetylpsilocin; 4-AcO-DMT)
3981:Pimagedine (aminoguanidine)
3851:Alpha-Fluoromethylhistidine
2368:Tooltip Monoamine oxidase B
2308:Tooltip Monoamine oxidase A
1937:tetracyclic antidepressants
776:Monoamine oxidase inhibitor
257:monoamine oxidase inhibitor
116:, is a naturally occurring
27:Group of chemical compounds
5654:
4025:Monoamine releasing agents
2791:Substrates→Products (with
1845:Dextromethorphan/bupropion
659:Harmine acid methyl ester:
563:1,2,3,4-tetrahydro-harmine
5618:Alkaloids found in plants
5061:α-Methyltryptophan (αMTP)
3993:
3139:
3014:
2786:
2779:Tooltip Monoamine oxidase
2568:
2503:
2492:
2409:
2396:
2180:
2167:
1943:
1926:
1557:
1539:
1393:10.1080/02652030400019844
966:10.1016/j.jep.2004.02.023
910:10.1016/j.fct.2009.12.019
849:10.1016/j.lfs.2005.05.074
488:Harmaline is also a RIMA.
267:. Harmala alkaloids from
3479:Epinephrine (adrenaline)
2812:Epinephrine (adrenaline)
2551:Rubidium chloride (RbCl)
670:-carboline-1-carboxylate
351:on these cancer cells."
271:have been used to treat
92:. The alkaloids include
5533:Substituted benzofurans
5268:β-carboline (norharman)
5115:AL-37350A (4,5-DHP-αMT)
4602:Desformylflustrabromine
4533:Aeruginascin (4-PO-TMT)
3956:Tooltip Diamine oxidase
2414:Atypical antipsychotics
4919:-acetylserotonin; NAS)
4760:Norbaeocystin (4-PO-T)
4483:5-(Nonyloxy)tryptamine
3856:Histidine methyl ester
1478:phytochem.nal.usda.gov
1063:"NCATS Inxight: Drugs"
877:Shulgin A, Shulgin A.
716:1-Carbamoyl-7-methoxy-
691:7-Methoxy-3,4-dihydro-
517:1-Methyl-4,9-dihydro-3
317:" caused by consuming
252:
149:central nervous system
40:
5309:DM-506 (ibogaminalog)
4981:4-HO-MPMI (lucigenol)
4799:Psilocybin (4-PO-DMT)
4707:Methylbutyltryptamine
4558:Baeocystin (4-PO-NMT)
4029:Monoamine neurotoxins
3971:Imidazole acetic acid
301:Unlike MAOIs such as
236:
35:
5207:Cyclized tryptamines
4712:Miprocin (4-HO-MiPT)
4682:Indolylethylfentanyl
4652:Ethocybin (4-PO-DET)
4577:Bufotenin (5-HO-DMT)
4572:Bufotenidine (5-HTQ)
3964:Substrates→Products:
3894:Substrates→Products:
3826:Substrates→Products:
3783:Substrates→Products:
3753:Substrates→Products:
3703:Substrates→Products:
3522:Substrates→Products:
3472:Substrates→Products:
3402:Substrates→Products:
3329:Substrates→Products:
3306:3,4-Dihydroxystyrene
3289:Substrates→Products:
2673:Substrates→Products:
2535:Hypericum perforatum
2403:Adjunctive therapies
1313:10.1155/2018/4810394
1086:Shulgin, Alexander.
403:7-Methoxy-1-methyl-9
269:Banisteriopsis caapi
212:Banisteriopsis caapi
177:Banisteriopsis caapi
125:Banisteriopsis caapi
77:Banisteriopsis caapi
5307:and related (e.g.,
4943:-Propionylmelatonin
4794:Psilocin (4-HO-DMT)
4692:Iprocin (4-HO-DiPT)
3444:Phenopicolinic acid
3168:Desmethylselegiline
1551:receptor modulators
1547:reuptake inhibitors
1436:1991PChem..30.1046A
1345:Massaro EJ (2002).
1248:2005PChem..66.1581J
741:1-Acetyl-7-methoxy-
323:monoamine oxidase B
277:benzodiazepine site
273:Parkinson's disease
145:monoamine oxidase A
4963:α-Alkyltryptamines
4935:-Butanoylmelatonin
4895:6-Methoxymelatonin
4890:6-Hydroxymelatonin
4875:5-Methoxyluzindole
4857:-Acetyltryptamines
4528:Acetryptine (5-AT)
4473:5-Methyltryptamine
4355:5-HTP (oxitriptan)
3620:2-Hydroxyestradiol
3601:4-Methoxyestradiol
3597:4-Hydroxyestradiol
3583:2-Methoxyestradiol
3579:2-Hydroxyestradiol
3349:2-Hydroxyestradiol
2595:Never to phase III
1484:on 4 February 2023
1005:10.1002/mdc3.12242
261:dimethyltryptamine
253:
159:compounds such as
151:by inhibiting the
41:
5605:
5604:
5407:Related compounds
5292:tetrahydroharmine
5105:αET (etryptamine)
4927:-Acetyltryptamine
4885:6-Fluoromelatonin
4880:6-Chloromelatonin
4870:2-Phenylmelatonin
4566:
4037:
4036:
4032:
3989:
3988:
3901:N-Methylhistamine
3831:
3798:
3797:
3786:N-Acetylserotonin
3760:N-Acetylserotonin
3730:Telotristat ethyl
3725:Fenclonine (PCPA)
3682:
3663:
3662:
3538:Homovanillic acid
3529:3-Methoxytyramine
3338:
3268:
3244:
3243:
3240:
3239:
3221:
3162:
3090:tetrahydroharmine
3070:Harmala alkaloids
2865:3-Methoxytyramine
2720:
2699:
2678:
2605:
2604:
2564:
2563:
2537:(St. John's Wort)
2488:
2487:
2453:lithium carbonate
2392:
2391:
2388:
2387:
2163:
2162:
2159:
2158:
1972:Amitriptylinoxide
1922:
1921:
1918:
1917:
1358:978-0-89603-796-0
1215:on 8 October 2007
789:Nicotiana rustica
734:Acetylnorharmine:
666:Methyl 7-methoxy-
542:Tetrahydroharmine
521:-pyridoindol-7-ol
249:ultraviolet light
141:Alexander Shulgin
131:is also found in
129:Tetrahydroharmine
44:Harmala alkaloids
18:Harmala alkaloids
16:(Redirected from
5645:
5439:7-Aza-5-MeO-DiPT
5424:5-Aza-4-MeO-DiPT
4814:Serotonin (5-HT)
4582:Convolutindole A
4564:
4087:1-Methylpsilocin
4064:
4057:
4050:
4041:
3995:
3957:
3953:
3887:
3883:
3829:
3819:
3815:
3809:
3776:
3772:
3746:
3742:
3696:
3692:
3686:
3672:
3625:2-Hydroxyestrone
3610:4-Methoxyestrone
3606:4-Hydroxyestrone
3592:2-Methoxyestrone
3588:2-Hydroxyestrone
3515:
3511:
3465:
3461:
3395:
3391:
3354:2-Hydroxyestrone
3339:-DOPA (levodopa)
3336:
3322:
3318:
3282:
3278:
3272:
3253:
3219:
3160:
3147:MAO-B selective:
3022:MAO-A-selective:
2986:Phenoxypropazine
2808:
2804:
2799:
2795:
2784:
2780:
2776:
2718:
2697:
2679:-DOPA (levodopa)
2676:
2666:
2662:
2656:
2632:
2625:
2618:
2609:
2545:
2511:
2494:
2467:triiodothyronine
2463:Thyroid hormones
2398:
2369:
2365:
2309:
2305:
2250:Phenoxypropazine
2182:
2169:
2113:
2109:
1955:
1951:
1945:
1928:
1807:
1803:
1774:
1770:
1741:
1737:
1708:
1704:
1675:
1671:
1627:
1623:
1569:
1565:
1559:
1541:
1521:
1514:
1507:
1498:
1493:
1491:
1489:
1480:. Archived from
1448:
1447:
1430:(3): 1046–1047.
1419:
1413:
1412:
1376:
1370:
1369:
1367:
1365:
1351:. Humana Press.
1342:
1336:
1335:
1325:
1315:
1291:
1285:
1279:
1268:
1267:
1231:
1225:
1224:
1222:
1220:
1196:
1190:
1189:
1187:
1185:
1171:
1165:
1164:
1162:
1160:
1146:
1140:
1139:
1129:
1097:
1091:
1084:
1078:
1077:
1075:
1073:
1059:
1053:
1052:
1041:
1035:
1034:
1024:
984:
978:
977:
949:
943:
936:
930:
929:
893:
887:
886:
879:"#13. HARMALINE"
874:
868:
867:
865:
863:
828:
822:
821:
813:
752:
727:
702:
684:Harmilinic acid:
677:
652:
622:
576:
534:
479:
420:
366:Poisons Standard
284:essential tremor
193:. The leaves of
21:
5653:
5652:
5648:
5647:
5646:
5644:
5643:
5642:
5608:
5607:
5606:
5601:
5419:4-Aza-5-MeO-DPT
5402:
5201:
5148:
4957:
4865:2-Iodomelatonin
4848:
4073:
4068:
4038:
4033:
3985:
3955:
3945:
3916:Diphenhydramine
3885:
3875:
3817:
3794:
3774:
3764:
3744:
3734:
3694:
3671:
3659:
3547:Normetanephrine
3513:
3503:
3463:
3453:
3393:
3383:
3320:
3310:
3280:
3263:
3252:
3250:Phenethylamines
3236:
3135:
3010:
3006:Tranylcypromine
2843:Normetanephrine
2806:
2797:
2778:
2768:
2664:
2647:
2636:
2606:
2601:
2600:
2585:Clinical trials
2560:
2499:
2484:
2480:
2472:
2457:lithium citrate
2405:
2384:
2367:
2364:
2354:
2307:
2304:
2294:
2270:Tranylcypromine
2176:
2155:
2139:
2111:
2101:
1953:
1939:
1914:
1823:
1805:
1795:
1772:
1762:
1739:
1729:
1706:
1696:
1673:
1663:
1644:Levomilnacipran
1625:
1615:
1567:
1553:
1535:
1528:Antidepressants
1525:
1487:
1485:
1468:Peganum harmala
1464:
1456:
1451:
1421:
1420:
1416:
1387:(11): 1041–50.
1378:
1377:
1373:
1363:
1361:
1359:
1344:
1343:
1339:
1293:
1292:
1288:
1280:
1271:
1242:(13): 1581–92.
1233:
1232:
1228:
1218:
1216:
1198:
1197:
1193:
1183:
1181:
1173:
1172:
1168:
1158:
1156:
1148:
1147:
1143:
1099:
1098:
1094:
1088:"#13 Harmaline"
1085:
1081:
1071:
1069:
1061:
1060:
1056:
1043:
1042:
1038:
986:
985:
981:
951:
950:
946:
937:
933:
895:
894:
890:
876:
875:
871:
861:
859:
830:
829:
825:
815:
814:
810:
806:
800:
791:(Aztec tobacco)
761:
640:
636:
632:
594:
590:
586:
555:
551:
547:
509:
505:
501:
454:
450:
446:
395:
391:
387:
378:
362:
357:
331:
315:cheese syndrome
296:ego dissolution
280:inverse agonist
231:
222:Peganum harmala
205:
172:Peganum harmala
64:(also known as
61:Peganum harmala
37:Peganum harmala
28:
23:
22:
15:
12:
11:
5:
5651:
5649:
5641:
5640:
5635:
5630:
5625:
5620:
5610:
5609:
5603:
5602:
5600:
5599:
5594:
5589:
5584:
5566:
5561:
5556:
5530:
5525:
5520:
5515:
5510:
5505:
5496:
5491:
5486:
5481:
5476:
5471:
5466:
5461:
5456:
5451:
5446:
5441:
5436:
5431:
5426:
5421:
5416:
5410:
5408:
5404:
5403:
5401:
5400:
5362:
5357:
5352:
5347:
5342:
5337:
5332:
5325:tabernanthalog
5299:
5246:
5241:
5227:
5222:
5217:
5211:
5209:
5203:
5202:
5200:
5199:
5194:
5189:
5184:
5179:
5174:
5169:
5164:
5158:
5156:
5150:
5149:
5147:
5146:
5141:
5132:
5127:
5122:
5117:
5112:
5107:
5102:
5089:
5076:
5063:
5058:
5053:
5048:
5043:
5038:
5033:
5028:
5023:
5018:
5013:
5008:
5003:
4998:
4993:
4988:
4983:
4978:
4973:
4967:
4965:
4959:
4958:
4956:
4955:
4950:
4945:
4937:
4929:
4921:
4915:Normelatonin (
4912:
4907:
4902:
4897:
4892:
4887:
4882:
4877:
4872:
4867:
4861:
4859:
4850:
4849:
4847:
4846:
4841:
4836:
4831:
4826:
4821:
4816:
4811:
4806:
4801:
4796:
4791:
4782:
4777:
4772:
4767:
4762:
4757:
4752:
4747:
4739:
4734:
4729:
4724:
4719:
4714:
4709:
4704:
4699:
4694:
4689:
4684:
4679:
4674:
4669:
4664:
4659:
4654:
4649:
4644:
4639:
4634:
4629:
4624:
4619:
4614:
4609:
4604:
4599:
4594:
4589:
4584:
4579:
4574:
4569:
4560:
4555:
4550:
4545:
4540:
4535:
4530:
4525:
4520:
4515:
4510:
4505:
4500:
4495:
4490:
4485:
4480:
4475:
4470:
4465:
4460:
4455:
4450:
4445:
4440:
4435:
4430:
4425:
4420:
4415:
4410:
4405:
4400:
4395:
4390:
4385:
4380:
4367:
4362:
4357:
4352:
4347:
4342:
4337:
4332:
4327:
4322:
4317:
4312:
4307:
4302:
4297:
4292:
4287:
4282:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4237:
4232:
4227:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4175:4-HO-5-MeO-DMT
4172:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4132:
4127:
4122:
4117:
4104:
4099:
4094:
4089:
4083:
4081:
4075:
4074:
4069:
4067:
4066:
4059:
4052:
4044:
4035:
4034:
3994:
3991:
3990:
3987:
3986:
3984:
3983:
3974:
3973:
3960:
3958:
3947:
3946:
3944:
3943:
3938:
3933:
3928:
3923:
3918:
3913:
3904:
3903:
3890:
3888:
3877:
3876:
3874:
3873:
3868:
3863:
3858:
3853:
3848:
3839:
3838:
3822:
3820:
3806:
3800:
3799:
3796:
3795:
3793:
3792:
3779:
3777:
3766:
3765:
3763:
3762:
3749:
3747:
3736:
3735:
3733:
3732:
3727:
3722:
3713:
3712:
3699:
3697:
3683:
3665:
3664:
3661:
3660:
3658:
3657:
3652:
3647:
3642:
3637:
3632:
3627:
3622:
3613:
3612:
3603:
3594:
3585:
3576:
3567:
3558:
3549:
3543:Norepinephrine
3540:
3531:
3518:
3516:
3505:
3504:
3502:
3501:
3496:
3491:
3482:
3481:
3468:
3466:
3455:
3454:
3452:
3451:
3446:
3441:
3436:
3431:
3426:
3421:
3412:
3411:
3398:
3396:
3385:
3384:
3382:
3381:
3376:
3371:
3366:
3361:
3359:3-Iodotyrosine
3356:
3351:
3342:
3341:
3325:
3323:
3312:
3311:
3309:
3308:
3299:
3298:
3285:
3283:
3269:
3265:norepinephrine
3246:
3245:
3242:
3241:
3238:
3237:
3235:
3234:
3229:
3224:
3215:
3210:
3205:
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3157:
3152:
3140:
3137:
3136:
3134:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3096:Methylene blue
3093:
3067:
3062:
3057:
3055:CX157 (Tyrima)
3052:
3047:
3042:
3037:
3032:
3027:
3015:
3012:
3011:
3009:
3008:
3003:
2998:
2993:
2988:
2983:
2978:
2973:
2968:
2963:
2958:
2953:
2948:
2943:
2938:
2933:
2928:
2923:
2918:
2913:
2908:
2903:
2898:
2893:
2888:Non-selective:
2881:
2880:
2871:
2862:
2853:
2840:
2831:
2818:
2787:
2781:
2770:
2769:
2767:
2766:
2761:
2756:
2751:
2746:
2737:
2736:
2727:
2715:
2713:Phenethylamine
2706:
2694:
2685:
2669:
2667:
2653:
2649:
2648:
2637:
2635:
2634:
2627:
2620:
2612:
2603:
2602:
2599:
2598:
2597:
2596:
2593:
2582:
2576:
2570:
2569:
2566:
2565:
2562:
2561:
2559:
2558:
2553:
2548:
2539:
2531:
2514:
2508:Ademetionine (
2504:
2501:
2500:
2497:
2490:
2489:
2486:
2485:
2483:
2482:
2478:
2470:
2460:
2446:
2441:
2410:
2407:
2406:
2401:
2394:
2393:
2390:
2389:
2386:
2385:
2383:
2382:
2373:
2371:
2362:
2356:
2355:
2353:
2352:
2347:
2342:
2337:
2332:
2327:
2322:
2313:
2311:
2302:
2296:
2295:
2293:
2292:
2283:
2282:
2273:
2272:
2267:
2262:
2257:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2202:
2197:
2188:
2186:
2178:
2177:
2172:
2165:
2164:
2161:
2160:
2157:
2156:
2154:
2153:
2147:
2145:
2141:
2140:
2138:
2137:
2132:
2127:
2122:
2116:
2114:
2103:
2102:
2100:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2027:Imipraminoxide
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1969:
1964:
1958:
1956:
1941:
1940:
1931:
1924:
1923:
1920:
1919:
1916:
1915:
1913:
1912:
1907:
1902:
1897:
1892:
1887:
1882:
1877:
1872:
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1831:
1829:
1825:
1824:
1822:
1821:
1816:
1810:
1808:
1797:
1796:
1794:
1793:
1788:
1783:
1777:
1775:
1764:
1763:
1761:
1760:
1755:
1750:
1744:
1742:
1731:
1730:
1728:
1727:
1722:
1717:
1711:
1709:
1698:
1697:
1695:
1694:
1689:
1684:
1678:
1676:
1665:
1664:
1662:
1661:
1656:
1651:
1646:
1641:
1636:
1634:Desvenlafaxine
1630:
1628:
1617:
1616:
1614:
1613:
1608:
1603:
1598:
1593:
1588:
1583:
1578:
1572:
1570:
1555:
1554:
1544:
1537:
1536:
1526:
1524:
1523:
1516:
1509:
1501:
1495:
1494:
1472:Zygophyllaceae
1462:
1455:
1454:External links
1452:
1450:
1449:
1424:Phytochemistry
1414:
1371:
1357:
1337:
1286:
1269:
1236:Phytochemistry
1226:
1191:
1166:
1141:
1112:(12): 1940–4.
1092:
1079:
1067:drugs.ncats.io
1054:
1036:
979:
944:
931:
888:
869:
843:(8): 795–802.
823:
807:
805:
802:
798:
797:
792:
785:
784:
778:
773:
770:Beta-carboline
767:
760:
757:
756:
755:
754:
753:
746:
736:
735:
731:
730:
729:
728:
721:
711:
710:
706:
705:
704:
703:
696:
686:
685:
681:
680:
679:
678:
671:
661:
660:
656:
655:
654:
653:
643:
642:
638:
634:
630:
626:
625:
624:
623:
613:
612:
611:
610:
596:
595:
592:
588:
584:
580:
579:
578:
577:
567:
566:
565:
564:
558:
557:
553:
549:
545:
538:
537:
536:
535:
525:
524:
523:
522:
512:
511:
507:
503:
499:
492:
491:
490:
489:
483:
482:
481:
480:
470:
469:
468:
467:
457:
456:
452:
448:
444:
437:
436:
435:
434:
424:
423:
422:
421:
411:
410:
409:
408:
398:
397:
393:
389:
385:
377:
376:Chemical forms
374:
361:
358:
356:
353:
330:
327:
230:
227:
225:(Syrian Rue).
204:
201:
165:norepinephrine
118:beta-carboline
74:), as well as
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
5650:
5639:
5636:
5634:
5631:
5629:
5626:
5624:
5621:
5619:
5616:
5615:
5613:
5598:
5595:
5593:
5590:
5588:
5585:
5582:
5578:
5574:
5570:
5567:
5565:
5562:
5560:
5557:
5554:
5550:
5546:
5542:
5538:
5534:
5531:
5529:
5526:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5506:
5504:
5502:
5497:
5495:
5492:
5490:
5487:
5485:
5482:
5480:
5477:
5475:
5472:
5470:
5467:
5465:
5462:
5460:
5457:
5455:
5452:
5450:
5447:
5445:
5442:
5440:
5437:
5435:
5432:
5430:
5427:
5425:
5422:
5420:
5417:
5415:
5414:2-Azapsilocin
5412:
5411:
5409:
5405:
5398:
5394:
5390:
5386:
5382:
5378:
5374:
5370:
5366:
5363:
5361:
5358:
5356:
5353:
5351:
5348:
5346:
5343:
5341:
5338:
5336:
5333:
5330:
5329:tabernanthine
5326:
5322:
5318:
5314:
5310:
5306:
5304:
5300:
5297:
5293:
5289:
5285:
5281:
5277:
5273:
5269:
5265:
5261:
5257:
5253:
5251:
5247:
5245:
5242:
5239:
5235:
5231:
5228:
5226:
5223:
5221:
5218:
5216:
5213:
5212:
5210:
5208:
5204:
5198:
5195:
5193:
5190:
5188:
5185:
5183:
5180:
5178:
5175:
5173:
5170:
5168:
5165:
5163:
5160:
5159:
5157:
5155:
5151:
5145:
5142:
5140:
5138:
5133:
5131:
5128:
5126:
5123:
5121:
5118:
5116:
5113:
5111:
5108:
5106:
5103:
5101:
5099:
5095:
5090:
5088:
5086:
5082:
5077:
5075:
5073:
5069:
5064:
5062:
5059:
5057:
5054:
5052:
5049:
5047:
5044:
5042:
5039:
5037:
5034:
5032:
5029:
5027:
5024:
5022:
5019:
5017:
5014:
5012:
5009:
5007:
5004:
5002:
4999:
4997:
4994:
4992:
4989:
4987:
4984:
4982:
4979:
4977:
4974:
4972:
4969:
4968:
4966:
4964:
4960:
4954:
4951:
4949:
4946:
4944:
4942:
4938:
4936:
4934:
4930:
4928:
4926:
4922:
4920:
4918:
4913:
4911:
4908:
4906:
4903:
4901:
4898:
4896:
4893:
4891:
4888:
4886:
4883:
4881:
4878:
4876:
4873:
4871:
4868:
4866:
4863:
4862:
4860:
4858:
4856:
4851:
4845:
4842:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4820:
4817:
4815:
4812:
4810:
4807:
4805:
4802:
4800:
4797:
4795:
4792:
4790:
4788:
4783:
4781:
4778:
4776:
4773:
4771:
4768:
4766:
4763:
4761:
4758:
4756:
4753:
4751:
4748:
4746:
4744:
4740:
4738:
4735:
4733:
4730:
4728:
4725:
4723:
4720:
4718:
4715:
4713:
4710:
4708:
4705:
4703:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4673:
4670:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4650:
4648:
4645:
4643:
4640:
4638:
4635:
4633:
4630:
4628:
4625:
4623:
4620:
4618:
4615:
4613:
4610:
4608:
4605:
4603:
4600:
4598:
4595:
4593:
4590:
4588:
4585:
4583:
4580:
4578:
4575:
4573:
4570:
4568:
4561:
4559:
4556:
4554:
4551:
4549:
4546:
4544:
4541:
4539:
4536:
4534:
4531:
4529:
4526:
4524:
4521:
4519:
4516:
4514:
4511:
4509:
4506:
4504:
4501:
4499:
4496:
4494:
4491:
4489:
4486:
4484:
4481:
4479:
4476:
4474:
4471:
4469:
4466:
4464:
4461:
4459:
4456:
4454:
4453:5-MeO-T-NBOMe
4451:
4449:
4446:
4444:
4441:
4439:
4436:
4434:
4431:
4429:
4426:
4424:
4421:
4419:
4416:
4414:
4411:
4409:
4406:
4404:
4401:
4399:
4396:
4394:
4391:
4389:
4386:
4384:
4381:
4379:
4377:
4373:
4368:
4366:
4365:5-MeO-34MPEMT
4363:
4361:
4358:
4356:
4353:
4351:
4348:
4346:
4343:
4341:
4338:
4336:
4333:
4331:
4328:
4326:
4323:
4321:
4318:
4316:
4313:
4311:
4308:
4306:
4303:
4301:
4298:
4296:
4293:
4291:
4288:
4286:
4283:
4281:
4278:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4236:
4233:
4231:
4228:
4226:
4223:
4221:
4218:
4216:
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4173:
4171:
4170:4-F-5-MeO-DMT
4168:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4114:
4110:
4105:
4103:
4102:2-Methyl-5-HT
4100:
4098:
4095:
4093:
4090:
4088:
4085:
4084:
4082:
4080:
4076:
4072:
4065:
4060:
4058:
4053:
4051:
4046:
4045:
4042:
4031:
4030:
4026:
4022:
4018:
4017:Serotonergics
4014:
4013:Melatonergics
4010:
4009:Dopaminergics
4006:
4002:
3999:
3992:
3982:
3979:
3976:
3975:
3972:
3968:
3965:
3962:
3961:
3959:
3954:
3948:
3942:
3939:
3937:
3934:
3932:
3929:
3927:
3924:
3922:
3919:
3917:
3914:
3912:
3909:
3906:
3905:
3902:
3898:
3895:
3892:
3891:
3889:
3884:
3878:
3872:
3869:
3867:
3864:
3862:
3859:
3857:
3854:
3852:
3849:
3847:
3844:
3841:
3840:
3837:
3833:
3827:
3824:
3823:
3821:
3816:
3810:
3807:
3805:
3801:
3791:
3787:
3784:
3781:
3780:
3778:
3773:
3767:
3761:
3757:
3754:
3751:
3750:
3748:
3743:
3737:
3731:
3728:
3726:
3723:
3721:
3718:
3715:
3714:
3711:
3707:
3704:
3701:
3700:
3698:
3693:
3687:
3684:
3680:
3676:
3670:
3666:
3656:
3653:
3651:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3618:
3615:
3614:
3611:
3607:
3604:
3602:
3598:
3595:
3593:
3589:
3586:
3584:
3580:
3577:
3575:
3571:
3568:
3566:
3562:
3559:
3557:
3553:
3550:
3548:
3544:
3541:
3539:
3535:
3532:
3530:
3526:
3523:
3520:
3519:
3517:
3512:
3506:
3500:
3497:
3495:
3492:
3490:
3487:
3484:
3483:
3480:
3476:
3473:
3470:
3469:
3467:
3462:
3456:
3450:
3447:
3445:
3442:
3440:
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3414:
3413:
3410:
3406:
3403:
3400:
3399:
3397:
3392:
3386:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3344:
3343:
3340:
3333:
3330:
3327:
3326:
3324:
3319:
3313:
3307:
3304:
3301:
3300:
3297:
3293:
3292:Phenylalanine
3290:
3287:
3286:
3284:
3279:
3273:
3270:
3266:
3261:
3257:
3251:
3247:
3233:
3230:
3228:
3225:
3223:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3158:
3156:
3153:
3151:
3148:
3145:
3142:
3141:
3138:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3091:
3087:
3083:
3079:
3075:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3020:
3017:
3016:
3013:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2987:
2984:
2982:
2979:
2977:
2974:
2972:
2969:
2967:
2964:
2962:
2959:
2957:
2956:Metfendrazine
2954:
2952:
2949:
2947:
2944:
2942:
2939:
2937:
2936:Isocarboxazid
2934:
2932:
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2907:
2904:
2902:
2901:Echinopsidine
2899:
2897:
2894:
2892:
2889:
2886:
2883:
2882:
2879:
2875:
2872:
2870:
2866:
2863:
2861:
2857:
2854:
2852:
2848:
2844:
2841:
2839:
2835:
2832:
2830:
2826:
2822:
2819:
2817:
2813:
2810:
2805:
2796:
2789:
2788:
2785:
2782:
2777:
2771:
2765:
2762:
2760:
2757:
2755:
2752:
2750:
2747:
2745:
2742:
2739:
2738:
2735:
2731:
2728:
2726:
2722:
2716:
2714:
2710:
2709:Phenylalanine
2707:
2705:
2701:
2695:
2693:
2689:
2686:
2684:
2680:
2674:
2671:
2670:
2668:
2663:
2657:
2654:
2650:
2646:
2643:
2640:
2633:
2628:
2626:
2621:
2619:
2614:
2613:
2610:
2594:
2592:
2589:
2588:
2586:
2583:
2580:
2577:
2575:
2572:
2571:
2567:
2557:
2554:
2552:
2549:
2547:
2540:
2538:
2536:
2532:
2529:
2525:
2521:
2520:neurosteroids
2518:
2515:
2513:
2506:
2505:
2502:
2498:Miscellaneous
2495:
2491:
2476:
2475:levothyroxine
2468:
2464:
2461:
2458:
2454:
2450:
2447:
2445:
2442:
2439:
2435:
2431:
2427:
2423:
2422:brexpiprazole
2419:
2415:
2412:
2411:
2408:
2404:
2399:
2395:
2381:
2378:
2377:Irreversible:
2375:
2374:
2372:
2366:
2357:
2351:
2348:
2346:
2343:
2341:
2338:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2315:
2314:
2312:
2306:
2297:
2291:
2288:
2285:
2284:
2281:
2278:
2275:
2274:
2271:
2268:
2266:
2263:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2243:
2241:
2238:
2236:
2233:
2231:
2228:
2226:
2223:
2221:
2218:
2216:
2213:
2211:
2210:Isocarboxazid
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2192:Irreversible:
2190:
2189:
2187:
2185:Non-selective
2183:
2179:
2175:
2170:
2166:
2152:
2149:
2148:
2146:
2142:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2117:
2115:
2110:
2104:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2082:Protriptyline
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2057:Nortriptyline
2055:
2053:
2052:Nitroxazepine
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1992:Demexiptiline
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1967:Amitriptyline
1965:
1963:
1960:
1959:
1957:
1952:
1946:
1942:
1938:
1934:
1929:
1925:
1911:
1908:
1906:
1903:
1901:
1898:
1896:
1893:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1832:
1830:
1826:
1820:
1817:
1815:
1812:
1811:
1809:
1804:
1798:
1792:
1789:
1787:
1784:
1782:
1779:
1778:
1776:
1771:
1765:
1759:
1756:
1754:
1751:
1749:
1746:
1745:
1743:
1738:
1732:
1726:
1723:
1721:
1718:
1716:
1713:
1712:
1710:
1705:
1699:
1693:
1690:
1688:
1685:
1683:
1680:
1679:
1677:
1672:
1666:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1631:
1629:
1624:
1618:
1612:
1609:
1607:
1604:
1602:
1599:
1597:
1594:
1592:
1589:
1587:
1584:
1582:
1579:
1577:
1574:
1573:
1571:
1566:
1560:
1556:
1552:
1548:
1542:
1538:
1533:
1529:
1522:
1517:
1515:
1510:
1508:
1503:
1502:
1499:
1483:
1479:
1475:
1473:
1469:
1463:
1461:
1458:
1457:
1453:
1445:
1441:
1437:
1433:
1429:
1425:
1418:
1415:
1410:
1406:
1402:
1398:
1394:
1390:
1386:
1382:
1375:
1372:
1360:
1354:
1350:
1349:
1341:
1338:
1333:
1329:
1324:
1319:
1314:
1309:
1305:
1301:
1297:
1290:
1287:
1284:
1278:
1276:
1274:
1270:
1265:
1261:
1257:
1253:
1249:
1245:
1241:
1237:
1230:
1227:
1214:
1210:
1206:
1202:
1195:
1192:
1180:
1176:
1170:
1167:
1155:
1151:
1145:
1142:
1137:
1133:
1128:
1123:
1119:
1115:
1111:
1107:
1103:
1096:
1093:
1089:
1083:
1080:
1068:
1064:
1058:
1055:
1050:
1046:
1040:
1037:
1032:
1028:
1023:
1018:
1014:
1010:
1006:
1002:
998:
994:
990:
983:
980:
975:
971:
967:
963:
959:
955:
948:
945:
941:
940:Phytochemical
935:
932:
927:
923:
919:
915:
911:
907:
904:(3): 839–45.
903:
899:
892:
889:
884:
880:
873:
870:
858:
854:
850:
846:
842:
838:
837:Life Sciences
834:
827:
824:
819:
812:
809:
803:
801:
796:
793:
790:
787:
786:
782:
779:
777:
774:
771:
768:
766:
763:
762:
758:
751:
747:
744:
740:
739:
738:
737:
733:
732:
726:
722:
719:
715:
714:
713:
712:
708:
707:
701:
697:
694:
690:
689:
688:
687:
683:
682:
676:
672:
669:
665:
664:
663:
662:
658:
657:
651:
647:
646:
645:
644:
629:Isoharmine: C
628:
627:
621:
617:
616:
615:
614:
608:
604:
600:
599:
598:
597:
582:
581:
575:
571:
570:
569:
568:
562:
561:
560:
559:
543:
540:
539:
533:
529:
528:
527:
526:
520:
516:
515:
514:
513:
497:
494:
493:
487:
486:
485:
484:
478:
474:
473:
472:
471:
466:-pyridoindole
465:
461:
460:
459:
458:
442:
439:
438:
432:
429:Harmine is a
428:
427:
426:
425:
419:
415:
414:
413:
412:
407:-pyridoindole
406:
402:
401:
400:
399:
383:
380:
379:
375:
373:
369:
367:
359:
354:
352:
350:
349:
344:
340:
336:
328:
326:
324:
320:
316:
312:
308:
304:
299:
297:
292:
287:
285:
281:
278:
274:
270:
266:
262:
258:
250:
246:
243:
239:
235:
228:
226:
224:
223:
217:
213:
209:
202:
200:
198:
197:
192:
191:
185:
183:
178:
173:
168:
166:
162:
158:
154:
150:
146:
142:
138:
134:
130:
126:
122:
119:
115:
111:
107:
103:
99:
95:
91:
87:
84:), leaves of
83:
79:
78:
73:
69:
68:
63:
62:
57:
53:
49:
45:
38:
34:
30:
19:
5633:Nitrariaceae
5500:
5484:Latrepirdine
5397:rescinnamine
5381:corynanthine
5335:Metralindole
5302:
5256:β-carbolines
5249:
5248:
5234:lysergamides
5225:Cyclic 3-OHM
5197:Zolmitriptan
5177:Frovatriptan
5136:
5097:
5093:
5084:
5080:
5074:-methyl-αMT)
5071:
5067:
5051:7-Methyl-αET
5046:7-Chloro-αMT
5041:6-Fluoro-αMT
5036:5-Methyl-αET
5011:5-Fluoro-αMT
5006:5-Fluoro-αET
5001:5-Ethoxy-αMT
4996:5-Chloro-αMT
4948:Piromelatine
4940:
4932:
4924:
4916:
4854:
4786:
4785:Psilacetin (
4742:
4677:Idalopirdine
4567:-tryptophan)
4523:7-Methyl-DMT
4518:6-Fluoro-DMT
4503:5,6-MDO-MiPT
4493:5,6-MDO-DiPT
4488:5,6-MeO-MiPT
4468:5-Methyl-DMT
4448:5-MeO-NBpBrT
4375:
4371:
4345:5-Fluoro-MET
4340:5-Fluoro-EPT
4335:5-Fluoro-DMT
4330:5-Fluoro-DET
4320:5-Ethoxy-DMT
4315:5-Chloro-DMT
4295:4,5-MDO-DiPT
4112:
4108:
3997:
3996:
3977:
3963:
3907:
3893:
3871:Tritoqualine
3842:
3825:
3782:
3752:
3716:
3702:
3650:Quinalizarin
3635:Neluxicapone
3616:
3556:Metanephrine
3521:
3485:
3471:
3434:Fusaric acid
3415:
3401:
3369:Bulbocapnine
3345:
3328:
3302:
3288:
3232:Tisolagiline
3227:Sembragiline
3218:Selegiline (
3146:
3143:
3121:Sercloremine
3101:Metralindole
3069:
3021:
3018:
2996:Procarbazine
2991:Pivhydrazine
2981:Pheniprazine
2906:Furazolidone
2887:
2884:
2821:Metanephrine
2790:
2740:
2672:
2652:Non-specific
2542:Oxitriptan (
2534:
2418:aripiprazole
2376:
2325:Metralindole
2316:
2286:
2276:
2255:Pivhydrazine
2245:Pheniprazine
2191:
2097:Trimipramine
2087:Quinupramine
1987:Clomipramine
1982:Butriptyline
1905:Teniloxazine
1900:Tandospirone
1885:Metryptamine
1880:Medifoxamine
1865:Indeloxazine
1819:Vortioxetine
1581:Escitalopram
1486:. Retrieved
1482:the original
1477:
1471:
1467:
1427:
1423:
1417:
1384:
1380:
1374:
1362:. Retrieved
1347:
1340:
1303:
1299:
1289:
1239:
1235:
1229:
1217:. Retrieved
1213:the original
1208:
1204:
1194:
1182:. Retrieved
1178:
1169:
1157:. Retrieved
1153:
1144:
1109:
1105:
1095:
1082:
1070:. Retrieved
1066:
1057:
1048:
1039:
999:(1): 19–26.
996:
992:
982:
957:
953:
947:
934:
901:
897:
891:
882:
872:
860:. Retrieved
840:
836:
826:
817:
811:
799:
772:(norharmane)
742:
717:
709:Harmanamide:
692:
667:
606:
602:
601:1-Methyl-3,4
583:Harmalane: C
518:
463:
404:
370:
363:
355:Legal status
346:
332:
300:
288:
268:
254:
245:fluorescence
220:
211:
207:
206:
196:P. incarnata
195:
188:
186:
176:
171:
169:
136:
132:
124:
113:
109:
90:coffee beans
75:
71:
65:
59:
50:that act as
46:are several
43:
42:
36:
29:
5638:Tryptamines
5581:naratriptan
5559:Tepirindole
5393:deserpidine
5373:rauwolscine
5321:noribogaine
5192:Sumatriptan
5187:Rizatriptan
5167:Donitriptan
5162:Almotriptan
4844:Z2876442907
4819:Solypertine
4727:Milipertine
4697:Lespedamine
4498:5,6-MDO-DMT
4478:5-MT-NB3OMe
4443:5-MeO-pyr-T
4360:5-MeO-2-TMT
4325:5-Ethyl-DMT
4305:5-Bromo-DMT
4290:4,5-MDO-DMT
4120:4,5-DHP-DMT
4079:Tryptamines
4071:Tryptamines
4005:Adrenergics
3978:Inhibitors:
3911:Amodiaquine
3908:Inhibitors:
3843:Inhibitors:
3717:Inhibitors:
3669:Tryptamines
3617:Inhibitors:
3552:Epinephrine
3486:Inhibitors:
3416:Inhibitors:
3364:Aquayamycin
3346:Inhibitors:
3303:Inhibitors:
3260:epinephrine
3150:Adarigiline
3144:Inhibitors:
3111:Moclobemide
3040:Brofaromine
3035:Befloxatone
3030:Bazinaprine
3019:Inhibitors:
2926:Iproclozide
2916:Hydralazine
2885:Inhibitors:
2807:Tooltip ALR
2744:Benserazide
2741:Inhibitors:
2581:from market
2524:brexanolone
2438:risperidone
2335:Moclobemide
2317:Reversible:
2277:Reversible:
2200:Iproclozide
2135:Setiptiline
2130:Mirtazapine
2120:Maprotiline
2077:Propizepine
2062:Noxiptiline
2047:Metapramine
2037:Lofepramine
2007:Dimetacrine
1997:Desipramine
1870:Flupentixol
1855:Etryptamine
1840:Amisulpride
1835:Agomelatine
1781:Etoperidone
1758:Setiptiline
1753:Mirtazapine
1725:Nomifensine
1682:Atomoxetine
1659:Venlafaxine
1649:Milnacipran
1591:Fluvoxamine
1306:: 4810394.
960:(1): 1–23.
918:10261/77694
862:21 November
820:. Elsevier.
208:Telepathine
203:Telepathine
114:banisterine
110:telepathine
5612:Categories
5573:avitriptan
5564:Tetrindole
5541:5-MeO-DiBF
5523:Sertindole
5503:)-69 (3IQ)
5494:Pirlindole
5469:EMD-386088
5385:ajmalicine
5377:spegatrine
5355:PNU-181731
5296:tryptoline
5244:Flucindole
5220:Ciclindole
5215:Bay R 1531
5172:Eletriptan
5031:5-MeO-MPMI
5021:5-MeO-αET
5016:5-iPrO-αMT
4839:Yuremamine
4834:Tryptophan
4829:Tryptamine
4775:Oxypertine
4687:Indorenate
4587:CP-132,484
4433:5-MeO-MiPT
4423:5-MeO-MALT
4413:5-MeO-EiPT
4398:5-MeO-DiPT
4383:5-MeO-DALT
4280:4-MeO-MiPT
4270:4-MeO-DiPT
4265:4-HO-pyr-T
4230:4-HO-McPeT
4165:4-AcO-MiPT
4150:4-AcO-MALT
4135:4-AcO-DiPT
4125:4-AcO-DALT
3931:Quinacrine
3866:Naringenin
3861:Meciadanol
3832:-Histidine
3706:Tryptophan
3640:Nitecapone
3630:Entacapone
3489:CGS-19281A
3439:Nepicastat
3424:Disulfiram
3419:Bupicomide
3374:Metirosine
3222:-Deprenyl)
3213:Safinamide
3208:Rasagiline
3193:Mofegiline
3188:Milacemide
3183:Lazabemide
3178:Ladostigil
3155:Almoxatone
3131:Toloxatone
3126:Tetrindole
3116:Pirlindole
3060:Eprobemide
3050:Clorgiline
3045:Cimoxatone
3025:Amiflamine
2976:Phenelzine
2971:Paraxazone
2951:Mebanazine
2931:Iproniazid
2921:Indantadol
2911:Guineesine
2896:Caroxazone
2764:Methyldopa
2734:Tryptamine
2730:Tryptophan
2700:-Histidine
2645:modulators
2642:metabolism
2556:Tryptophan
2528:zuranolone
2434:quetiapine
2430:olanzapine
2426:lurasidone
2380:Selegiline
2370:-selective
2350:Toloxatone
2345:Tetrindole
2340:Pirlindole
2320:Eprobemide
2310:-selective
2290:Bifemelane
2280:Caroxazone
2240:Phenelzine
2225:Mebanazine
2205:Iproniazid
2092:Tianeptine
2072:Pipofezine
2042:Melitracen
2022:Imipramine
2002:Dibenzepin
1962:Amineptine
1910:Tianeptine
1895:Pivagabine
1890:Oxaflozane
1850:Esketamine
1814:Vilazodone
1786:Nefazodone
1715:Amineptine
1692:Viloxazine
1687:Reboxetine
1639:Duloxetine
1611:Zimelidine
1606:Sertraline
1601:Paroxetine
1586:Fluoxetine
1576:Citalopram
1488:11 January
1179:erowid.org
1154:erowid.org
1072:28 January
804:References
745:-carboline
720:-carboline
348:P. harmala
337:effect on
329:Anticancer
307:reversible
303:phenelzine
216:telepathic
190:Passiflora
182:hypnagogic
153:metabolism
137:P. harmala
72:Syrian Rue
5623:Ayahuasca
5592:VU6067416
5577:LY-334370
5549:dimemebfe
5518:RU-24,969
5513:Ro60-0213
5508:Ro60-0175
5489:LY-367265
5459:BRL-54443
5454:AL-38022A
5444:AAZ-A-154
5389:reserpine
5369:yohimbine
5365:Yohimbans
5350:PNU-22394
5345:PHA-57378
5317:ibogamine
5305:alkaloids
5272:harmaline
5260:6-MeO-THH
5252:alkaloids
5230:Ergolines
5130:CP-135807
5125:BW-723C86
5026:5-MeO-αMT
4910:Melatonin
4905:Luzindole
4458:5-MeS-DMT
4438:5-MeO-NMT
4428:5-MeO-MET
4418:5-MeO-EPT
4408:5-MeO-DPT
4403:5-MeO-DMT
4393:5-MeO-DET
4388:5-MeO-DBT
4350:5-HO-DiPT
4285:4-PrO-DMT
4275:4-MeO-DMT
4260:4-HO-PiPT
4250:4-HO-NALT
4245:4-HO-MsBT
4235:4-HO-MiPT
4225:4-HO-McPT
4215:4-HO-MALT
4205:4-HO-DSBT
4195:4-HO-DiPT
4180:4-HO-DALT
4160:4-AcO-DPT
4155:4-AcO-MET
4145:4-AcO-NMT
4140:4-AcO-EPT
4130:4-AcO-DET
3998:See also:
3967:Histamine
3936:SKF-91488
3926:Metoprine
3921:Harmaline
3897:Histamine
3836:Histamine
3804:Histamine
3790:Melatonin
3756:Serotonin
3679:melatonin
3675:serotonin
3655:Tolcapone
3645:Opicapone
3494:SKF-64139
3449:Tropolone
3203:Pargyline
3163:-Deprenyl
3106:Minaprine
3086:norharman
3078:harmaline
3001:Safrazine
2966:Octamoxin
2961:Nialamide
2946:Linezolid
2941:Isoniazid
2874:Serotonin
2759:Genistein
2749:Carbidopa
2721:-Tyrosine
2704:Histamine
2692:Serotonin
2639:Monoamine
2591:Phase III
2579:Withdrawn
2444:Buspirone
2330:Minaprine
2265:Tedizolid
2260:Safrazine
2235:Octamoxin
2230:Nialamide
2220:Linezolid
2215:Isoniazid
2125:Mianserin
2067:Opipramol
2032:Iprindole
2012:Dosulepin
1977:Amoxapine
1933:Tricyclic
1791:Trazodone
1748:Mianserin
1720:Bupropion
1654:Tofenacin
1596:Indalpine
1545:Specific
1409:216644379
1106:Neurology
1013:2330-1619
885:. Erowid.
795:Hordenine
441:Harmaline
360:Australia
335:cytotoxic
311:selective
265:purgative
238:Harmaline
161:serotonin
157:monoamine
106:shamanism
98:harmaline
82:ayahuasca
48:alkaloids
5587:VER-3323
5569:Triptans
5464:CP-94253
5449:AL-34662
5360:RU-28306
5313:ibogaine
5288:pinoline
5276:harmalol
5182:L-694247
5154:Triptans
5135:IPAP (α,
4991:4-Me-αMT
4986:4-Me-αET
4976:4-HO-αMT
4809:RS134-49
4662:FGIN-143
4657:FGIN-127
4370:5-MeO-7,
4255:4-HO-NMT
4240:4-HO-MPT
4220:4-HO-MET
4210:4-HO-EPT
4200:4-HO-DPT
4190:4-HO-DET
4185:4-HO-DBT
4097:2-Me-DET
4092:2-HO-NMT
3846:Catechin
3720:AGN-2979
3525:Dopamine
3499:SKF-7698
3429:Dopastin
3405:Dopamine
3379:Oudenone
3332:Tyrosine
3296:Tyrosine
3256:dopamine
3198:Nicotine
3065:Esuprone
2891:Benmoxin
2856:Dopamine
2725:Tyramine
2683:Dopamine
2517:GABAkine
2195:Benmoxin
2151:Tiazesim
1875:Ketamine
1860:Gepirone
1401:15764332
1332:29568754
1264:15949825
1136:12499487
1031:30713897
974:15261959
926:20036304
857:16139309
759:See also
603:-dihydro
496:Harmalol
319:tyramine
291:cannabis
133:B. caapi
121:alkaloid
102:harmalol
5571:(e.g.,
5535:(e.g.,
5367:(e.g.,
5284:harmine
5280:harmane
5264:9-Me-BC
5258:(e.g.,
5250:Harmala
5236:(e.g.,
5120:BNC-210
4971:2,α-DMT
4953:TIK-301
4824:ST-1936
4543:AGH-192
4538:AGH-107
4513:5,7-DHT
4508:5,6-DHT
3941:Tacrine
3173:Ethanol
3074:harmine
3072:(e.g.,
2449:Lithium
2017:Doxepin
1549:and/or
1432:Bibcode
1323:5820675
1244:Bibcode
1127:4992345
1022:6353393
765:Harmane
433:(RIMA).
382:Harmine
275:. As a
242:harmine
94:harmine
86:tobacco
5597:YM-348
5553:mebfap
5434:5-MIAL
5429:5-HIAL
5070:-DMT (
4770:O-4310
4732:MS-245
4667:FT-104
4632:E-6837
4627:E-6801
4548:AH-494
3082:harman
2878:5-HIAA
2574:WHO-EM
2287:Mixed:
2144:Others
1828:Others
1736:NaSSAs
1407:
1399:
1364:4 June
1355:
1330:
1320:
1262:
1219:4 June
1184:19 May
1159:19 May
1134:
1124:
1029:
1019:
1011:
972:
924:
855:
783:(RIMA)
247:under
139:. Dr.
67:Harmal
5537:3-APB
5528:SN-22
5340:NDTDI
5303:Iboga
5139:-DPT)
4804:Pyr-T
4553:ALiPT
3741:AANAT
3710:5-HTP
3565:MOPEG
3561:DOPEG
3534:DOPAC
2860:DOPAC
2688:5-HTP
2544:5-HTP
2108:TeCAs
1769:SARIs
1703:NDRIs
1622:SNRIs
1564:SSRIs
1405:S2CID
56:seeds
5545:BPAP
5474:I-32
5254:and
5232:and
5144:MPMI
5100:-TMS
5087:-TMT
4780:PiPT
4765:NTBT
4737:MSBT
4717:MiPT
4672:HIOC
4642:EMDT
4637:EiPT
4612:DiPT
4592:DALT
4378:-TMT
4310:5-CT
4300:5-BT
4115:-TMT
3882:HNMT
3771:ASMT
3570:DOMA
3510:COMT
3460:PNMT
2847:MHPG
2838:DHMA
2825:MHPG
2816:DHMA
2794:ALDH
2754:DFMD
2661:AAAD
2510:SAMe
1950:TCAs
1935:and
1670:NRIs
1532:N06A
1490:2023
1397:PMID
1366:2020
1353:ISBN
1328:PMID
1304:2018
1260:PMID
1221:2007
1186:2022
1161:2022
1132:PMID
1074:2020
1027:PMID
1009:ISSN
970:PMID
922:PMID
864:2023
853:PMID
743:beta
718:beta
693:beta
668:beta
607:beta
343:K562
341:and
339:HL60
309:and
240:and
229:Uses
163:and
135:and
112:and
88:and
5479:IAL
5238:LSD
5110:αMT
4755:NMT
4750:NET
4722:MPT
4702:MET
4647:EPT
4622:DPT
4617:DMT
4607:DET
4597:DBT
3952:DAO
3814:HDC
3691:TPH
3574:VMA
3390:DBH
3277:PAH
2869:HVA
2851:VMA
2829:VMA
2803:ALR
2775:MAO
2473:),
2361:MAO
2301:MAO
1802:SMS
1440:doi
1389:doi
1318:PMC
1308:doi
1252:doi
1122:PMC
1114:doi
1017:PMC
1001:doi
962:doi
914:hdl
906:doi
845:doi
544:: C
498:: C
443:: C
384:: C
155:of
70:or
58:of
5614::
5579:,
5575:,
5551:,
5547:,
5543:,
5539:,
5395:,
5391:,
5387:,
5383:,
5379:,
5375:,
5371:,
5327:,
5323:,
5319:,
5315:,
5311:,
5294:,
5290:,
5286:,
5282:,
5278:,
5274:,
5270:,
5266:,
5262:,
5092:α,
5079:α,
5066:α,
4107:2,
4027:•
4023:•
4019:•
4015:•
4011:•
4007:•
4003:•
3677:,
3317:TH
3258:,
3088:,
3084:,
3080:,
3076:,
2809:):
2587::
2526:,
2481:))
2477:(T
2469:(T
2455:,
2436:,
2432:,
2428:,
2424:,
2420:,
1476:.
1438:.
1428:30
1426:.
1403:.
1395:.
1385:21
1383:.
1326:.
1316:.
1302:.
1298:.
1272:^
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