290:
195:
645:
hordenine in raw barley around 0.7 μg/g; in green malts (i.e. barley that had been soaked in water for 2 days then germinated for 4 days), the mean concentration was about 21 μg/g, and in kilned malts (i.e. green malts that had been heated in a kiln for 1–2 days), the mean concentration was about 28 μg/g. When only green malt roots were examined, their mean content of hordenine was roughly 3363 μg/g, whereas the mean level in kilned malt roots was around 4066 μg/g.
24:
837:
paralysis, with death occurring as a result of respiratory arrest. In a subsequent paper, Camus reported that the intravenous (IV) administration of some hundreds of mg of hordenine sulfate to dogs or rabbits caused an increase in blood pressure and changes in the rhythm and force of contraction of the heart, noting also that the drug was not orally active.
33:
454:
731:" which is listed as an ingredient on the labels of some nutritional supplements is in all likelihood simply hordenine hydrochloride, since the "description" of "methyl hordenine HCl" given by virtually all bulk suppliers of this substance corresponds to that for hordenine hydrochloride (or possibly just hordenine). Five
847:
In a 1995 study, Hapke and
Strathmann reported that in dogs and rats, hordenine produced a positive inotropic effect on the heart (i.e. increased the strength of contraction), increased systolic and diastolic blood pressure, and increased the volume of peripheral blood flow. Movements of the gut were
648:
In barley, hordenine levels reach a maximum within 5–11 days of germination, then slowly decrease until only traces remain after one month. Furthermore, hordenine is localized primarily in the roots. In comparing literature values for hordenine concentrations in "barley" or barley "malt", therefore,
832:
The first pharmacological study of hordenine to be recorded is that of
Heffter, who was also the first to isolate it. Using the sulfate salt (see "Chemistry"), Heffter gave a subcutaneous dose of 0.3 g to a 2.8-kg cat (about 107 mg/kg), and observed no effects besides violent vomiting; the cat
932:
values given in the literature are: >100 mg/kg (mouse; IP), as HCl salt: 113.5 mg/kg (mouse; route of administration unspecified) Minimum lethal dose (as sulfate salt): 300 mg/kg (dog; IV); 2000 mg/kg (dog; oral); 250 mg/kg (rabbit; IV); 300 mg/kg (guinea pig; IV);
644:
contained about 11–13 mg/L, and malt contained about 67 μg/g of hordenine. The hordenine content of various malts and malt fractions was extensively studied by
Poocharoen himself, who also provided a good coverage of related literature up to 1983. This researcher found a mean concentration of
653:
of malted barley, but not in "whole" malt, where his figures of 21-28 μg/g are more consistent with McFarlane's figure of about 67 μg/g. However, a wide range of variability is seen; a study by Lovett and co-workers of 43 different barley lines found concentrations of hordenine in roots ranging
843:
More modern studies were carried out by Frank and coworkers, who reported that IV administration of 2 mg/kg of hordenine to horses produced substantial respiratory distress, increased the rate of respiration by 250%, doubled the heart rate, and caused sweating without changes in basal body
1907:
Bunzow, James R.; Sonders, Mark S.; Arttamangkul, Seksiri; Harrison, Laura M.; Zhang, Ge; Quigley, Denise I.; Darland, Tristan; Suchland, Katherine L.; Pasumamula, Shailaja; Kennedy, James L.; Olson, Susan B.; Magenis, R. Ellen; Amara, Susan G.; Grandy, David K. (1 December 2001). "Amphetamine,
836:
Working with Léger's (see "Occurrence") hordenine sulfate, Camus determined minimum lethal doses for the dog, rabbit, guinea pig, and rat (see "Toxicology"). The associated symptoms of toxicity following parenteral doses were: excitation, vomiting, respiratory difficulties, convulsions, and
2122:
Bernays, E. A.; Oppenheim, S.; Chapman, R. F.; Kwon, H.; Gould, F. (1 February 2000). "Taste
Sensitivity of Insect Herbivores to Deterrents is Greater in Specialists Than in Generalists: A Behavioral Test of the Hypothesis with Two Closely Related Caterpillars".
943:, Australian researchers determined that the lowest doses of hordenine that would induce symptoms of "staggers" in sheep were 20 mg/kg IV, and 800 mg/kg orally. However, the cardiac symptoms of "sudden death" could not be evinced by hordenine.
535:, from which it is biosynthetically derived and with which it shares some pharmacological properties (see below). As of September 2012, hordenine is widely sold as an ingredient of nutritional supplements, with the claims that it is a stimulant of the
588:
Hordenine is present in a fairly wide range of plants, notably amongst the cacti, but has also been detected i n some algae and fungi. It occurs in grasses, and is found at significantly high concentrations in the seedlings of cereals such as
1744:
968:(NDMA), and was investigated as a possible precursor for the significant amounts of NDMA once found in beer, it was eventually established that the levels of hordenine present in malt were too low to account for the observed levels of NDMA.
886:, but a 25 μM concentration of the drug did potentiate its response to submaximal doses of NE, and inhibited its response to tyramine. However, the response to NE of isolated vas deferens taken from rats chronically treated with
649:
consideration should be made of the age and parts of the plant being analyzed: the figure of about 2,000 μg/g cited in the review by Smith, for example, is consistent with
Poocharoen's figures for the hordenine levels in the
2094:
Harley, K. L. S.; Thorsteinson, A. J. (1 May 1967). "The influence of plant chemicals on the feeding behavior, development, and survival of the two-striped grasshopper, Melanoplus bivittatus (Say), Acrididae: Orthoptera".
936:
From experiments aimed at identifying the toxin responsible for producing the locomotor disorder ("staggers") and rapidly lethal cardiac toxicosis ("sudden death") periodically observed in livestock feeding on the grass
833:
behaved normally within 45 mins. He also took a dose of 100 mg orally himself, without experiencing any observable effect. However, the alkaloid was observed to produce a paralysis of the nervous system in frogs.
654:
from 1 to 2625 μg/g fresh weight. These workers concluded that hordenine production was not under significant genetic control, but much more susceptible to environmental factors such as light duration.
2067:
Poocharoen, Boonthong.; Barbour, James F.; Libbey, Leonard M.; Scanlan, Richard A. (November 1992). "Precursors of N-nitrosodimethylamine in malted barley. 1. Determination of hordenine and gramine".
551:. These effects are generally not reproduced by oral administration of the drug in test animals, and virtually no scientific reports of the effects of hordenine in human beings have been published.
640:, beer and malt have been examined by several groups of investigators for the presence of hordenine. Citing a 1965 study by McFarlane, Poocharoen reported that beer contained ~ 12–24 mg/L,
539:, and has the ability to promote weight loss by enhancing metabolism. In experimental animals, given sufficiently large doses parenterally (by injection), hordenine does produce an increase in
1589:
Cheng, Chao-Shing; Ferber, Claus; Bashford, Raymond I.; Grillot, Gerald F. (September 1951). "A New
Synthesis of Hordenine and Other p-Dialkylaminoethylphenols and Some of Their Derivatives".
783:; the N,N-dimethyl-4-nitro-phenethylamine was reduced to N,N-dimethyl-4-amino-phenethylamine with Sn/HCl; this amine was finally converted to hordenine by diazotization/hydrolysis using NaNO
5990:
5985:
844:
temperature or behavior. All effects disappeared within 30 mins. The same dose of hordenine given orally did not produce any of the effects seen after parenteral administration.
585:
subsequently showed that these alkaloids were identical and proposed the correct molecular structure for this substance, for which the name "hordenine" was ultimately retained.
467:
2219:
1020:
Hordenine has some plant growth-inhibiting properties: Liu and Lovett reported that, at a concentration of 50 ppm, it reduced the radicle length in seedlings of white mustard (
1428:
Lovett, John V.; Hoult, Anne H. C.; Christen, Olaf (August 1994). "Biologically active secondary metabolites of barley. IV. Hordenine production by different barley lines".
1908:
3,4-Methylenedioxymethamphetamine, Lysergic Acid
Diethylamide, and Metabolites of the Catecholamine Neurotransmitters Are Agonists of a Rat Trace Amine Receptor".
2032:
Bourke, Ca; Carrigan, Mj; Dixon, Rj (July 1988). "Experimental evidence that tryptamine alkaloids do not cause
Phalaris aquatica sudden death syndrome in sheep".
1823:
Barwell, C J; Basma, A N; Lafi, M A K; Leake, L D (12 April 2011). "Deamination of hordenine by monoamine oxidase and its action on vasa deferentia of the rat".
810:-demethylated and converted to the iodide by heating with HI; the resulting p-hydroxy-phenylethyl iodide was then heated with dimethylamine to give hordenine.
339:
3840:
6020:
6015:
5068:
5018:
6035:
6010:
1493:
Kappe, Thomas; Armstrong, Marvin D. (May 1965). "Ultraviolet
Absorption Spectra and Apparent Acidic Dissociation Constants of Some Phenolic Amines 1".
6030:
6025:
6005:
6000:
4399:
4362:
2212:
1866:
Yokoo, Y.; Kohda, H.; Kusumoto, A.; Naoki, H.; Matsumoto, N.; Amachi, T.; Suwa, Y.; Fukazawa, H.; Ishida, H.; Tsuji, K.; Nukaya, H. (1 March 1999).
802:
A more efficient synthetic route was described by Chang and coworkers, who also provided references to earlier syntheses. This synthesis began with
1213:
Wheaton, T. A.; Stewart, I. (June 1970). "The distribution of tyramine, N-methyltyramine, hordenine, octopamine, and synephrine in higher plants".
4166:
912:
cells, hordenine, at a concentration of 1 μM, had almost identical potency to that of the same concentration of β-phenethylamine in stimulating
5038:
4346:
2158:
Liu, D. L.; Lovett, J. V. (October 1993). "Biologically active secondary metabolites of barley. II. Phytotoxicity of barley allelochemicals".
5563:
3985:
3277:
2625:
681:(tyramine methylpherase), but if the same enzyme is responsible for the second methylation that actually produces hordenine is uncertain.
619:) (about 0.1%). Reti, in his 1953 review of naturally occurring phenethylamines, notes that the richest source of hordenine is the cactus
1091:
The level of hordenine in ungerminated barley is negligible, but rises as germination (the first part of the "malting" process) proceeds.
6405:
3191:
2503:
2205:
1743:
Frank, M.; Weckman, T. J.; Wood, T.; Woods, W. E.; Tai, Chen L.; Chang, Shih-Ling; Ewing, A.; Blake, J. W.; Tobin, T. (November 1990).
735:
compounds would correspond to the name "methyl hordenine HCl", if it were interpreted according to the rules of chemical nomenclature:
4935:
3995:
3302:
2645:
6501:
5063:
5053:
5033:
4040:
1324:
1291:
890:
was not affected by hordenine. The investigators concluded that hordenine acted as an inhibitor of NE reuptake in rat vas deferens.
304:
848:
inhibited. Additional experiments on isolated tissue lead these investigators to conclude that hordenine was an indirectly acting
5573:
5391:
5058:
5043:
5028:
4811:
4000:
3307:
2650:
1471:
573:), naming it "anhalin". Twelve years later, E. Léger independently isolated an alkaloid which he named hordenine from germinated
1785:
Hapke, HJ; Strathmann, W (June 1995). "Pharmakologische
Wirkungen des Hordenin" [Pharmacological effects of hordenine].
775:
The first synthesis of hordenine is due to Barger: 2-phenylethyl alcohol was first converted to 2-phenylethyl chloride using PCl
5686:
5386:
5336:
5048:
4171:
3692:
2937:
916:
production through the rTAR1. The potency of tyramine in this receptor preparation was slightly higher than that of hordenine.
6126:
5995:
5980:
5975:
5558:
4366:
4136:
3980:
3543:
3512:
3287:
2806:
2780:
2635:
913:
901:: 83 nM/kg of hordenine (corresponding to about 14 mg/kg of the free base) enhancing gastrin release by roughly 60%.
5970:
5965:
5553:
5548:
5313:
4392:
4025:
3975:
3970:
3687:
3282:
2630:
1955:[Studies on Chemical Protectors against Radiation. XVII. Radioprotective Activities of Phenethylamine Compounds].
474:
5927:
4930:
4342:
4151:
4141:
4121:
4080:
4055:
4005:
3915:
3522:
3517:
3312:
2790:
2785:
2655:
678:
247:
779:; this chloride was reacted with dimethylamine to form N,N-dimethyl-phenylethylamine, which was then nitrated using HNO
6400:
5907:
5902:
4947:
4161:
4156:
4131:
4085:
3795:
3527:
3507:
3131:
3059:
2428:
2358:
268:
1705:
Rietschel, Hans Georg (1 March 1937). "Zur Pharmakologie des Hordenins" [On the pharmacology of hordenine].
821:
in the presence of 10% Pd-on-charcoal catalyst. The labelled C in the hordenine is thus the C which is β- to the N.
559:
The first report of the isolation from a natural source of the compound which is now known as hordenine was made by
5538:
4416:
4408:
3712:
3662:
5851:
5681:
4878:
3126:
2423:
2236:
2228:
976:
The pharmacokinetics of hordenine have been studied in horses. After IV administration of the drug, the α-phase T
1643:
Russo, C. A.; Gros, E. G. (August 1981). "Synthesis of 4-|2-(dimethylamino) ethyl-2-C| phenol (hordenine-α-C)".
4385:
4111:
3910:
3633:
3186:
2906:
2483:
1247:
764:
677:, and which, in turn is methylated to hordenine. The first step in this sequence is accomplished by the enzyme
1616:
Digenis, George A.; Burkett, J. W.; Mihranian, V. (April 1972). "A convenient synthesis of 2 - - hordenine".
112:
5917:
5876:
5600:
5468:
5463:
5453:
5381:
5371:
5125:
5115:
5098:
4957:
4197:
4075:
3890:
3850:
3815:
3805:
3079:
3069:
2378:
2368:
1188:
190:
6077:
6045:
5954:
5593:
5361:
4998:
4907:
4899:
4891:
4883:
4358:
4354:
4222:
4126:
4090:
4065:
3502:
3387:
2775:
2683:
1067:
962:
752:
728:
536:
510:
840:
The cardiovascular and other effects of hordenine were reviewed in detail by Reitschel, writing in 1937.
152:
6511:
5912:
5856:
5729:
5714:
5703:
5356:
5093:
5073:
4217:
4060:
3379:
3337:
2675:
2593:
1004:; the estimated concentration of hordenine that reduced feeding duration to 50% of control was 0.4M for
748:
744:
740:
736:
569:
544:
1134:
Léger, E. (1906). "Sur l'hordenine: alcaloide nouveau retiré des germes, dits touraillons, de l'orge".
694:
Since the hordenine molecule contains both a basic (amine) and acidic (phenol) functional group, it is
6233:
6092:
6087:
5744:
5734:
5724:
5588:
5376:
5328:
5273:
5263:
5013:
4350:
4070:
4045:
3905:
3860:
3810:
3425:
3369:
3251:
3181:
2896:
2691:
2553:
2478:
1057:
1052:
905:
625:
45:
6395:
6141:
5944:
5891:
5543:
5458:
5448:
5396:
5366:
5302:
5189:
5120:
5110:
4993:
4212:
3950:
3800:
3642:
3420:
3342:
3176:
3074:
3064:
2987:
2921:
2598:
2488:
2373:
2363:
2286:
732:
285:
78:
5754:
5749:
4851:
4227:
3563:
3558:
3054:
2821:
2353:
2183:
2140:
1933:
1848:
1722:
1453:
1170:
497:
class that occurs naturally in a variety of plants, taking its name from one of the most common,
4284:
4709:
6082:
5829:
5819:
5789:
5719:
5411:
5154:
4826:
3438:
3262:
3109:
2724:
2558:
2407:
2175:
2049:
1974:
1925:
1889:
1840:
1802:
1794:
1767:
1510:
1445:
1320:
1287:
1222:
947:
939:
605:
4754:
4749:
4744:
4739:
4729:
4724:
4719:
4714:
4704:
4694:
4684:
4664:
4654:
4649:
4644:
4459:
6506:
5824:
5804:
5644:
5308:
5283:
5227:
4867:
4624:
4619:
4569:
4116:
3960:
3870:
3759:
3623:
3497:
3410:
3267:
3003:
2891:
2770:
2714:
2563:
2302:
2167:
2132:
2104:
2076:
2041:
1964:
1917:
1879:
1832:
1759:
1714:
1652:
1625:
1598:
1571:
1546:
1502:
1437:
1408:
1372:
1312:
1279:
1256:
1162:
1042:
898:
671:
514:
432:
362:
4589:
4479:
4469:
4464:
1868:"Isolation from beer and structural determination of a potent stimulant of gastrin release"
256:
172:
6420:
6263:
6184:
5431:
5416:
5323:
5298:
5223:
5158:
5003:
4915:
4050:
3895:
3638:
3553:
3443:
3332:
3114:
2977:
2916:
2911:
2816:
2729:
2588:
2412:
2276:
615:
595:
88:
289:
194:
6454:
6335:
6248:
5578:
5199:
4862:
3885:
3648:
3578:
3400:
3297:
3211:
2846:
2704:
2583:
2513:
2045:
1836:
1763:
933:
2000 mg/kg (guinea pig; subcutaneous); about 1000 mg/kg (rat; subcutaneous).
853:
582:
560:
548:
540:
529:
494:
445:
132:
1479:
1413:
1396:
1316:
1283:
6495:
6470:
6465:
6380:
6289:
6268:
6242:
6200:
6065:
5809:
5664:
5513:
5436:
5174:
4796:
4781:
3618:
3608:
3548:
3471:
3349:
3327:
3136:
2982:
2886:
2876:
2811:
2744:
2605:
2438:
2281:
1260:
1174:
814:
421:
411:
183:
1937:
1852:
1726:
1672:
L. Camus (1906). "L'hordénine, son degré de toxicité, symptômes de l'intoxication."
6460:
6375:
6253:
6208:
6156:
6097:
6055:
5794:
5441:
5219:
5214:
5164:
5145:
4821:
4321:
4248:
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4187:
3935:
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3790:
3593:
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3094:
2962:
2957:
2861:
2841:
2749:
2523:
2518:
2498:
2418:
2393:
2261:
2256:
2187:
2144:
1969:
1952:
1457:
887:
883:
818:
600:
236:
1343:
McFarlane, W. D. (1965). "Tyrosine derived amines and phenols in wort and beer".
6480:
6445:
6415:
6345:
6340:
6315:
6213:
6116:
5769:
5759:
5739:
5693:
5674:
5654:
5633:
5421:
5406:
5341:
5293:
5233:
5204:
5184:
5150:
5078:
4872:
4806:
4316:
4301:
4146:
4030:
3940:
3880:
3588:
3433:
3415:
3231:
3226:
3171:
3166:
3104:
3099:
3038:
3018:
2856:
2719:
2615:
2533:
2528:
2468:
2463:
2403:
2398:
2337:
2317:
1745:"Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse"
1072:
426:
173 °C (343 °F; 446 K) at 11 mm Hg; sublimes at 140–150 °C
1369:
Determination of selected secondary and tertiary amine alkaloids in barley malt
23:
6450:
6385:
6365:
6360:
6355:
6350:
6330:
6320:
6294:
6273:
6228:
6223:
6192:
6161:
6146:
6136:
6050:
5881:
5844:
5834:
5814:
5774:
5764:
5619:
5615:
5605:
5401:
5351:
5346:
5278:
5268:
5253:
5248:
5238:
5169:
5140:
5135:
5008:
4942:
4925:
4836:
4831:
4801:
4291:
4232:
4015:
4010:
3965:
3955:
3945:
3855:
3845:
3774:
3769:
3603:
3598:
3583:
3452:
3448:
3405:
3374:
3354:
3322:
3272:
3241:
3146:
3141:
3089:
3084:
3028:
3023:
3013:
2871:
2866:
2851:
2836:
2709:
2699:
2670:
2610:
2578:
2568:
2543:
2473:
2443:
2433:
2388:
2383:
2327:
2322:
2312:
2136:
1884:
1867:
1062:
959:
849:
824:
Hordenine labelled with C at the position α- to the N has also been prepared,
695:
390:
163:
2197:
1994:"Central effects of the constituents of Mimosa opthalmocentra Mart. ex Benth"
1798:
6430:
6325:
6238:
6218:
6151:
6040:
5871:
5839:
5784:
5779:
5288:
5258:
5209:
5194:
5130:
4816:
4447:
4442:
4437:
4432:
4427:
4311:
4306:
4279:
4253:
4207:
4202:
4020:
3733:
3628:
3613:
3359:
3317:
3196:
3161:
2901:
2881:
2660:
2573:
2493:
2458:
1656:
1629:
1278:. The Alkaloids: Chemistry and Pharmacology. Vol. 35. pp. 77–154.
1153:
Späth, E. (1919). "Über die Anhalonium-Alkaloide. I. Anhalin und Mezcalin".
1047:
760:
2179:
1929:
1893:
1707:
Naunyn-Schmiedebergs Archiv für experimentelle Pathologie und Pharmakologie
1514:
1449:
2053:
1921:
1844:
1806:
1771:
1311:. The Alkaloids: Chemistry and Physiology. Vol. 3. pp. 313–338.
1226:
6435:
6281:
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5861:
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5659:
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5426:
5318:
5243:
4791:
4326:
4106:
3930:
3925:
3875:
3865:
3764:
3492:
3466:
3461:
3395:
3364:
3236:
3206:
3151:
3033:
3008:
2972:
2967:
2765:
2739:
2734:
2665:
2538:
2508:
2448:
2332:
2307:
2271:
2266:
1978:
1575:
1037:
928:
in mice, by intraperitoneal (IP) administration: 299 mg/kg. Other LD
879:
705:
s for protonated hordenine are 9.78 (phenolic H) and 10.02 (ammonium H).
667:
532:
490:
2080:
1602:
1506:
992:
Hordenine has been found to act as a feeding deterrent to grasshoppers (
6475:
6440:
6370:
6131:
5533:
5498:
5179:
5103:
5088:
4734:
4699:
4689:
4679:
4674:
4669:
4659:
3156:
2453:
2171:
2021:(10th ed.). Rahway, New Jersey: Merck & Co. 1983. p. 687.
1993:
1718:
1441:
1245:
Smith, T. A. (1977). "Phenethylamine and related compounds in plants".
1166:
1025:
951:
909:
894:
610:
223:
1377:
32:
6390:
6310:
6175:
6166:
6107:
5610:
5528:
5518:
5508:
5493:
5483:
5478:
5083:
4983:
4786:
4764:
4759:
4639:
4634:
4629:
4614:
4609:
4604:
4579:
4544:
4539:
4534:
4529:
4524:
4519:
4514:
3830:
3820:
3256:
2826:
590:
574:
498:
143:
2108:
1559:
852:
agent that produced its pharmacological effects by releasing stored
444:
Except where otherwise noted, data are given for materials in their
313:
InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
767:
that cannot be protonated, hence cannot form a hydrochloride salt.
323:
InChI=1/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
211:
6425:
5583:
5503:
5473:
5023:
4973:
4968:
4841:
4769:
4594:
4559:
4499:
4484:
4377:
4035:
3900:
3743:
3728:
3702:
3682:
3568:
2831:
2620:
1688:
L. Camus (1906), "Action de sulfate d'hordenine sur circulation."
904:
In a study of the effects of a large number of compounds on a rat
872:
860:
123:
111:
101:
5937:
5568:
5523:
5488:
4988:
4978:
4774:
4599:
4584:
4574:
4564:
4554:
4549:
4509:
4504:
4494:
4489:
4474:
4454:
3990:
3920:
3738:
3707:
3697:
3292:
2640:
641:
637:
633:
202:
4381:
2201:
6410:
273:
416:
116 to 117 °C (241 to 243 °F; 389 to 390 K)
1951:
Shinoda, Masato; Ohta, Setsuko; Takagi, Yoshinari (1977).
1560:"CCXXXV.—Synthesis of hordenine, the alkaloid from barley"
1276:
Chapter 2 β-Phenethylamines and Ephedrines of Plant Origin
1547:
http://www.alibaba.com/showroom/methyl-hordenine-hcl.html
763:, but is excluded from the possibilities because it is a
759:-methyl hordenine is better known as the natural product
882:, hordenine did not produce contraction of isolated rat
629:), which was found to contain 0.5–5.0% of the alkaloid.
2938:
806:-methoxy-phenylethyl alcohol, which was simultaneously
712:
Cl, m.p. 178 °C, and hordenine sulfate, (R-NH
462:
1992:
Batista, Leonia Maria; Almeida, R. Nobrega de (1997).
1645:
Journal of Labelled Compounds and Radiopharmaceuticals
897:
release in the rat, being essentially equipotent with
893:
Hordenine has been found to be a potent stimulant of
701:
The apparent (see original article for discussion) pK
563:
in 1894, who extracted this alkaloid from the cactus
859:
Hordenine was found to be a selective substrate for
6303:
6064:
5953:
5890:
5702:
5632:
4956:
4415:
4266:
3661:
2936:
2235:
3663:
1024:) by around 7%; admixture with an equal amount of
813:Radio-labelled hordenine has been prepared by the
2237:
1953:"放射線障害防護薬剤に関する研究(第17報)フェネチラミン系化合物の放射線障害防護効力について"
980:was found to be about 3 mins., and the β-phase T
871:= 128 nM/mg protein/h. It was not deaminated by
235:
946:Although hordenine is capable of reacting with
87:
1395:Mann, Jay D.; Mudd, S. Harvey (January 1963).
708:Common salts are hordenine hydrochloride, R-NH
4393:
2213:
8:
662:Hordenine is biosynthesized by the stepwise
636:, is used extensively in the production of
4400:
4386:
4378:
3672:
2947:
2246:
2220:
2206:
2198:
2069:Journal of Agricultural and Food Chemistry
1028:markedly enhanced this inhibitory effect.
288:
193:
171:
15:
1968:
1883:
1472:"Tyrosine metabolism - Reference pathway"
1412:
1376:
255:
1738:
1736:
1591:Journal of the American Chemical Society
1362:
1360:
1358:
1356:
1354:
2943:Tooltip Norepinephrine releasing agents
1476:Kyoto Encyclopedia of Genes and Genomes
1390:
1388:
1240:
1238:
1236:
1104:
1084:
543:, as well as other disturbances of the
528:-dimethyl derivative of the well-known
505:species). Chemically, hordenine is the
344:
309:
284:
66:-Dimethyltyramine; Peyocactin; Anhaline
1818:
1816:
1668:
1666:
1110:
1108:
184:
1338:
1336:
1115:Heffter, A. (1894). "Ueber Pellote".
316:Key: KUBCEEMXQZUPDQ-UHFFFAOYSA-N
151:
131:
7:
1825:Journal of Pharmacy and Pharmacology
1787:Deutsche Tierärztliche Wochenschrift
1482:on 2019-07-26 – via genome.jp.
817:of a mixture of 2--tyramine and 40%
755:- each in the form of its HCl salt;
632:Since barley, via its conversion to
438:high in: ethanol; ether; chloroform
6406:Lysergic acid 2,4-dimethylazetidide
326:Key: KUBCEEMXQZUPDQ-UHFFFAOYAA
226:
210:
3668:Tooltip Serotonin releasing agents
2046:10.1111/j.1751-0813.1988.tb14462.x
1837:10.1111/j.2042-7158.1989.tb06492.x
1764:10.1111/j.2042-3306.1990.tb04312.x
14:
2242:Tooltip Dopamine releasing agents
1397:"Alkaloids and Plant Metabolism"
875:from rat intestinal epithelium.
452:
380:
374:
31:
22:
5337:N,alpha-Diethylphenylethylamine
4363:Monoamine metabolism modulators
1401:Journal of Biological Chemistry
448:(at 25 °C , 100 kPa).
1970:10.1248/yakushi1947.97.10_1117
1495:Journal of Medicinal Chemistry
1367:Poocharoen, Boonthong (1983).
670:, which is first converted to
599:) (about 0.2%, or 2000 μg/g),
383:
368:
1:
4347:Monoamine reuptake inhibitors
4343:Receptor/signaling modulators
2034:Australian Veterinary Journal
1618:Journal of Labelled Compounds
1414:10.1016/S0021-9258(19)84008-5
1317:10.1016/S1876-0813(08)60144-X
1284:10.1016/S0099-9598(08)60123-6
4299:Adrenergic release blockers:
2001:Acta Farmaceutica Bonaerense
1309:Chapter 22 β-Phenethylamines
1261:10.1016/0031-9422(77)83004-5
1117:Arch. Exp. Pathol. Pharmakol
679:tyramine N-methyltransferase
6401:Lysergic acid 2-butyl amide
2160:Journal of Chemical Ecology
2125:Journal of Chemical Ecology
2097:Canadian Journal of Zoology
1430:Journal of Chemical Ecology
6528:
6411:Lysergic acid diethylamide
2229:Monoamine releasing agents
996:), and to caterpillars of
4335:
4241:
4180:
4099:
3783:
3752:
3721:
3675:
3536:
3485:
3047:
2996:
2950:
2799:
2758:
2346:
2295:
2249:
1752:Equine Veterinary Journal
724:, m.p. 211 °C.
442:
355:
335:
300:
71:
56:
44:
39:
30:
21:
6502:Phenethylamine alkaloids
5301:(Dextromethamphetamine,
3634:Phthalimidopropiophenone
2907:Phthalimidopropiophenone
1345:Proc. Europ. Brew. Conv.
1189:"Visionary Cactus Guide"
863:, from rat liver, with K
765:quaternary ammonium salt
5955:Phenylalkylpyrrolidines
5877:Methylenedioxycathinone
5554:3,4-MDA (tenamfetamine)
2137:10.1023/A:1005430010314
1885:10.1093/alcalc/34.2.161
1657:10.1002/jlcr.2580180813
1630:10.1002/jlcr.2590080208
1558:Barger, George (1909).
1274:Lundström, Jan (1989).
4879:β-Methylphenethylamine
4873:α-Methylphenethylamine
1910:Molecular Pharmacology
1872:Alcohol and Alcoholism
1155:Monatshefte für Chemie
1068:O-desmethylvenlafaxine
621:Trichocereus candicans
537:central nervous system
6070:(and close relatives)
5569:MDMA (midomafetamine)
4911:-Methylphenethylamine
4903:-Methylphenethylamine
4895:-Methylphenethylamine
4887:-Methylphenethylamine
4367:Monoamine neurotoxins
3991:MDMA (midomafetamine)
3338:Dextromethamphetamine
3293:MDMA (midomafetamine)
2641:MDMA (midomafetamine)
2594:Dextromethamphetamine
1922:10.1124/mol.60.6.1181
994:Melanoplus bivittatus
966:-nitrosodimethylamine
908:(rTAR1) expressed in
623:(now reclassified as
570:Ariocarpus fissuratus
567:(now reclassified as
565:Anhalonium fissuratus
6234:N,N-Dimethyldopamine
5892:Phenylisobutylamines
5589:Naphthylaminopropane
5274:Isopropylamphetamine
5264:4-Hydroxyamphetamine
3370:Naphthylaminopropane
3252:4-Hydroxyamphetamine
2897:Naphthylaminopropane
2554:4-Hydroxyamphetamine
1576:10.1039/CT9099502193
1564:J. Chem. Soc., Trans
1058:4-Hydroxyamphetamine
1053:N,N-Dimethyldopamine
906:trace amine receptor
753:4-O-methyl hordenine
729:methyl hordenine HCl
626:Echinopsis candicans
609:) (about 0.2%), and
46:Preferred IUPAC name
6396:Lysergic acid amide
6142:Ethylnorepinephrine
5945:Phenylisobutylamine
5397:Phenylpropanolamine
5332:-Norpseudoephedrine
5303:Levomethamphetamine
5190:Dimethylamphetamine
3976:MDA (tenamfetamine)
3643:Levopropylhexedrine
3421:Phenylpropanolamine
3343:Levomethamphetamine
3283:MDA (tenamfetamine)
3177:Dimethylamphetamine
2988:Pseudophenmetrazine
2922:Levopropylhexedrine
2631:MDA (tenamfetamine)
2599:Levomethamphetamine
2489:Dimethylamphetamine
2287:Pseudophenmetrazine
2081:10.1021/jf00023a033
1603:10.1021/ja01153a008
1507:10.1021/jm00327a018
998:Heliothis virescens
988:Insect interactions
984:was about 35 mins.
547:, respiratory, and
433:Solubility in water
398: g·mol
18:
4852:Phenylethanolamine
2172:10.1007/BF00979660
1719:10.1007/BF01929674
1442:10.1007/BF02066235
1167:10.1007/BF01524590
1016:Plant interactions
1002:Heliothis subflexa
948:nitrosating agents
749:3-methyl hordenine
745:2-methyl hordenine
741:β-methyl hordenine
737:α-methyl hordenine
475:Infobox references
347:Oc1ccc(cc1)CCN(C)C
16:
6489:
6488:
5830:N-Ethylpentedrone
5790:Dimethylcathinone
5412:Propylamphetamine
5155:Dextroamphetamine
4827:Methallylescaline
4375:
4374:
4370:
4262:
4261:
3657:
3656:
3439:Propylamphetamine
3263:Iofetamine (123I)
3110:Dextroamphetamine
2932:
2931:
2725:Propylamphetamine
2559:Iofetamine (123I)
2408:Dextroamphetamine
2166:(10): 2231–2244.
2075:(11): 2216–2221.
1963:(10): 1117–1124.
1545:See, for example:
1527:CAS No. 6027-23-2
1307:Reti, L. (1953).
940:Phalaris aquatica
606:Panicum miliaceum
483:Chemical compound
481:
480:
269:CompTox Dashboard
113:Interactive image
6519:
6195:
6187:
6178:
6169:
6110:
6071:
5825:N-Ethylhexedrone
5805:Hydroxybupropion
5645:Chlorphentermine
5622:
5331:
5309:Methoxyphenamine
5284:Lisdexamfetamine
5228:Levofenfluramine
4868:Phenpromethamine
4402:
4395:
4388:
4379:
4337:
4289:Antagonist-like:
3961:Levofenfluramine
3871:Chlorphentermine
3788:Phenethylamines:
3760:4-Methylaminorex
3673:
3669:
3665:
3624:Methylhexanamine
3455:
3411:Phenpromethamine
3268:Lisdexamfetamine
3052:Phenethylamines:
2948:
2944:
2940:
2892:Methylhexanamine
2715:Phenpromethamine
2564:Lisdexamfetamine
2351:Phenethylamines:
2247:
2243:
2239:
2222:
2215:
2208:
2199:
2192:
2191:
2155:
2149:
2148:
2119:
2113:
2112:
2091:
2085:
2084:
2064:
2058:
2057:
2029:
2023:
2022:
2015:
2009:
2008:
1998:
1989:
1983:
1982:
1972:
1948:
1942:
1941:
1916:(6): 1181–1188.
1904:
1898:
1897:
1887:
1863:
1857:
1856:
1820:
1811:
1810:
1782:
1776:
1775:
1749:
1740:
1731:
1730:
1702:
1696:
1686:
1680:
1670:
1661:
1660:
1651:(8): 1185–1187.
1640:
1634:
1633:
1613:
1607:
1606:
1597:(9): 4081–4084.
1586:
1580:
1579:
1555:
1549:
1543:
1537:
1536:CAS No. 622-64-0
1534:
1528:
1525:
1519:
1518:
1490:
1484:
1483:
1478:. Archived from
1468:
1462:
1461:
1436:(8): 1945–1954.
1425:
1419:
1418:
1416:
1392:
1383:
1382:
1380:
1364:
1349:
1348:
1340:
1331:
1330:
1304:
1298:
1297:
1271:
1265:
1264:
1242:
1231:
1230:
1210:
1204:
1203:
1201:
1199:
1185:
1179:
1178:
1150:
1144:
1143:
1131:
1125:
1124:
1112:
1092:
1089:
1043:N-Methyltyramine
972:Pharmacokinetics
899:N-methyltyramine
666:-methylation of
465:
459:
456:
455:
406:colorless solid
397:
385:
382:
376:
370:
363:Chemical formula
293:
292:
277:
275:
259:
239:
228:
214:
197:
186:
175:
155:
135:
115:
91:
35:
26:
19:
6527:
6526:
6522:
6521:
6520:
6518:
6517:
6516:
6492:
6491:
6490:
6485:
6421:Methoxphenidine
6299:
6264:Normetanephrine
6193:
6185:
6176:
6167:
6108:
6069:
6068:
6060:
5949:
5940:
5886:
5847:
5698:
5689:
5677:
5628:
5620:
5596:
5444:
5432:Tranylcypromine
5417:Pseudoephedrine
5329:
5324:Norfenfluramine
5299:Methamphetamine
5224:Dexfenfluramine
5159:Levoamphetamine
5106:
5004:Bromo-DragonFLY
4952:
4938:
4916:Methylphenidate
4847:
4417:Phenethylamines
4411:
4409:Phenethylamines
4406:
4376:
4371:
4331:
4274:DAT modulators:
4258:
4237:
4176:
4095:
4051:Norfenfluramine
3896:Dexfenfluramine
3779:
3748:
3726:Aminotetralins:
3717:
3667:
3653:
3639:Propylhexedrine
3532:
3481:
3453:
3444:Pseudoephedrine
3333:Methamphetamine
3115:Levoamphetamine
3043:
2992:
2978:Phendimetrazine
2942:
2928:
2917:Propylhexedrine
2912:Phenylbiguanide
2795:
2754:
2730:Pseudoephedrine
2589:Methamphetamine
2413:Levoamphetamine
2342:
2291:
2277:Phendimetrazine
2241:
2231:
2226:
2196:
2195:
2157:
2156:
2152:
2121:
2120:
2116:
2109:10.1139/z67-043
2093:
2092:
2088:
2066:
2065:
2061:
2031:
2030:
2026:
2017:
2016:
2012:
1996:
1991:
1990:
1986:
1959:(in Japanese).
1957:Yakugaku Zasshi
1950:
1949:
1945:
1906:
1905:
1901:
1865:
1864:
1860:
1822:
1821:
1814:
1784:
1783:
1779:
1747:
1742:
1741:
1734:
1704:
1703:
1699:
1687:
1683:
1671:
1664:
1642:
1641:
1637:
1615:
1614:
1610:
1588:
1587:
1583:
1557:
1556:
1552:
1544:
1540:
1535:
1531:
1526:
1522:
1492:
1491:
1487:
1470:
1469:
1465:
1427:
1426:
1422:
1394:
1393:
1386:
1366:
1365:
1352:
1342:
1341:
1334:
1327:
1306:
1305:
1301:
1294:
1273:
1272:
1268:
1244:
1243:
1234:
1212:
1211:
1207:
1197:
1195:
1187:
1186:
1182:
1152:
1151:
1147:
1133:
1132:
1128:
1114:
1113:
1106:
1101:
1096:
1095:
1090:
1086:
1081:
1034:
1018:
990:
983:
979:
974:
957:
931:
927:
922:
878:In contrast to
870:
867:= 479 μM, and V
866:
830:
798:
794:
790:
786:
782:
778:
773:
723:
719:
715:
711:
704:
692:
687:
675:-methyltyramine
660:
616:Sorghum vulgare
596:Hordeum vulgare
579:Hordeum vulgare
557:
549:nervous systems
518:-methyltyramine
484:
477:
472:
471:
470: ?)
461:
457:
453:
449:
435:
395:
379:
373:
365:
351:
348:
343:
342:
331:
328:
327:
324:
318:
317:
314:
308:
307:
296:
278:
271:
262:
242:
229:
217:
178:
158:
138:
118:
105:
94:
81:
67:
52:
51:
12:
11:
5:
6525:
6523:
6515:
6514:
6509:
6504:
6494:
6493:
6487:
6486:
6484:
6483:
6478:
6473:
6468:
6463:
6458:
6455:Levosalbutamol
6448:
6443:
6438:
6433:
6428:
6423:
6418:
6413:
6408:
6403:
6398:
6393:
6388:
6383:
6378:
6373:
6368:
6363:
6358:
6353:
6348:
6343:
6338:
6336:Desvenlafaxine
6333:
6328:
6323:
6318:
6313:
6307:
6305:
6301:
6300:
6298:
6297:
6292:
6287:
6279:
6271:
6266:
6261:
6251:
6249:Norepinephrine
6246:
6236:
6231:
6226:
6221:
6216:
6211:
6206:
6198:
6190:
6188:-Phenylalanine
6182:
6173:
6164:
6159:
6154:
6149:
6144:
6139:
6134:
6129:
6124:
6119:
6114:
6105:
6100:
6095:
6090:
6085:
6080:
6074:
6072:
6066:Catecholamines
6062:
6061:
6059:
6058:
6053:
6048:
6043:
6038:
6033:
6028:
6023:
6018:
6013:
6008:
6003:
5998:
5993:
5988:
5983:
5978:
5973:
5968:
5959:
5957:
5951:
5950:
5948:
5947:
5935:
5930:
5925:
5920:
5915:
5910:
5905:
5896:
5894:
5888:
5887:
5885:
5884:
5879:
5874:
5869:
5864:
5859:
5854:
5842:
5837:
5832:
5827:
5822:
5817:
5812:
5807:
5802:
5797:
5792:
5787:
5782:
5777:
5772:
5767:
5762:
5757:
5752:
5747:
5742:
5737:
5732:
5727:
5722:
5717:
5708:
5706:
5700:
5699:
5697:
5696:
5684:
5672:
5667:
5662:
5657:
5652:
5647:
5638:
5636:
5630:
5629:
5627:
5626:
5613:
5608:
5603:
5591:
5586:
5581:
5579:Methamnetamine
5576:
5571:
5566:
5561:
5556:
5551:
5546:
5541:
5536:
5531:
5526:
5521:
5516:
5511:
5506:
5501:
5496:
5491:
5486:
5481:
5476:
5471:
5466:
5461:
5456:
5451:
5439:
5434:
5429:
5424:
5419:
5414:
5409:
5404:
5399:
5394:
5389:
5384:
5379:
5374:
5369:
5364:
5359:
5354:
5349:
5344:
5339:
5334:
5326:
5321:
5316:
5311:
5306:
5296:
5291:
5286:
5281:
5276:
5271:
5266:
5261:
5256:
5251:
5246:
5241:
5236:
5231:
5217:
5212:
5207:
5202:
5200:Etilamfetamine
5197:
5192:
5187:
5182:
5177:
5172:
5167:
5162:
5148:
5143:
5138:
5133:
5128:
5123:
5118:
5113:
5101:
5096:
5091:
5086:
5081:
5076:
5071:
5066:
5061:
5056:
5051:
5046:
5041:
5036:
5031:
5026:
5021:
5016:
5011:
5006:
5001:
4996:
4991:
4986:
4981:
4976:
4971:
4962:
4960:
4954:
4953:
4951:
4950:
4945:
4933:
4928:
4919:
4918:
4913:
4905:
4897:
4889:
4881:
4876:
4870:
4865:
4863:Phenethylamine
4860:
4845:
4844:
4839:
4834:
4829:
4824:
4819:
4814:
4809:
4804:
4799:
4794:
4789:
4784:
4778:
4777:
4772:
4767:
4762:
4757:
4752:
4747:
4742:
4737:
4732:
4727:
4722:
4717:
4712:
4707:
4702:
4697:
4692:
4687:
4682:
4677:
4672:
4667:
4662:
4657:
4652:
4647:
4642:
4637:
4632:
4627:
4622:
4617:
4612:
4607:
4602:
4597:
4592:
4587:
4582:
4577:
4572:
4567:
4562:
4557:
4552:
4547:
4542:
4537:
4532:
4527:
4522:
4517:
4512:
4507:
4502:
4497:
4492:
4487:
4482:
4477:
4472:
4467:
4462:
4457:
4451:
4450:
4445:
4440:
4435:
4430:
4421:
4419:
4413:
4412:
4407:
4405:
4404:
4397:
4390:
4382:
4373:
4372:
4336:
4333:
4332:
4330:
4329:
4324:
4319:
4314:
4309:
4304:
4295:
4294:
4282:
4270:
4268:
4264:
4263:
4260:
4259:
4257:
4256:
4251:
4242:
4239:
4238:
4236:
4235:
4230:
4225:
4220:
4215:
4210:
4205:
4200:
4195:
4190:
4181:
4178:
4177:
4175:
4174:
4169:
4164:
4159:
4154:
4149:
4144:
4139:
4134:
4129:
4124:
4119:
4114:
4109:
4100:
4097:
4096:
4094:
4093:
4088:
4083:
4078:
4073:
4068:
4063:
4058:
4053:
4048:
4043:
4038:
4033:
4028:
4023:
4018:
4013:
4008:
4003:
3998:
3993:
3988:
3983:
3978:
3973:
3968:
3963:
3958:
3953:
3948:
3943:
3938:
3933:
3928:
3923:
3918:
3913:
3908:
3903:
3898:
3893:
3888:
3886:Metamfepramone
3883:
3878:
3873:
3868:
3863:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3803:
3798:
3793:
3784:
3781:
3780:
3778:
3777:
3772:
3767:
3762:
3753:
3750:
3749:
3747:
3746:
3741:
3736:
3731:
3722:
3719:
3718:
3716:
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3676:
3670:
3659:
3658:
3655:
3654:
3652:
3651:
3649:Tuaminoheptane
3646:
3636:
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3579:Cyclopentamine
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3537:
3534:
3533:
3531:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3486:
3483:
3482:
3480:
3479:
3474:
3469:
3464:
3459:
3446:
3441:
3436:
3431:
3423:
3418:
3413:
3408:
3403:
3401:Phenethylamine
3398:
3393:
3385:
3377:
3372:
3367:
3362:
3357:
3352:
3347:
3346:
3345:
3340:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3298:Metamfepramone
3295:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3254:
3249:
3244:
3239:
3234:
3229:
3224:
3219:
3214:
3212:Etilamfetamine
3209:
3204:
3199:
3194:
3189:
3184:
3179:
3174:
3169:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3118:
3117:
3112:
3102:
3097:
3092:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3048:
3045:
3044:
3042:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
2997:
2994:
2993:
2991:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2951:
2945:
2934:
2933:
2930:
2929:
2927:
2926:
2925:
2924:
2914:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2847:Cyclopentamine
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2800:
2797:
2796:
2794:
2793:
2788:
2783:
2778:
2773:
2768:
2759:
2756:
2755:
2753:
2752:
2747:
2742:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2705:Phenethylamine
2702:
2697:
2689:
2681:
2673:
2668:
2663:
2658:
2653:
2648:
2643:
2638:
2633:
2628:
2623:
2618:
2613:
2608:
2603:
2602:
2601:
2596:
2586:
2584:Metamfepramone
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2536:
2531:
2526:
2521:
2516:
2514:Etilamfetamine
2511:
2506:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2441:
2436:
2431:
2426:
2421:
2416:
2410:
2401:
2396:
2391:
2386:
2381:
2376:
2371:
2366:
2361:
2356:
2347:
2344:
2343:
2341:
2340:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2296:
2293:
2292:
2290:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2250:
2244:
2233:
2232:
2227:
2225:
2224:
2217:
2210:
2202:
2194:
2193:
2150:
2131:(2): 547–563.
2114:
2103:(3): 305–319.
2086:
2059:
2040:(7): 218–220.
2024:
2010:
1984:
1943:
1899:
1878:(2): 161–168.
1858:
1831:(6): 421–423.
1812:
1793:(6): 228–232.
1777:
1758:(6): 437–441.
1732:
1713:(2): 387–408.
1697:
1681:
1662:
1635:
1624:(2): 231–235.
1608:
1581:
1550:
1538:
1529:
1520:
1501:(3): 368–374.
1485:
1463:
1420:
1407:(1): 381–385.
1384:
1350:
1332:
1325:
1299:
1292:
1266:
1248:Phytochemistry
1232:
1205:
1180:
1145:
1126:
1103:
1102:
1100:
1097:
1094:
1093:
1083:
1082:
1080:
1077:
1076:
1075:
1070:
1065:
1060:
1055:
1050:
1045:
1040:
1033:
1030:
1017:
1014:
1008:and 0.08M for
989:
986:
981:
977:
973:
970:
958:) to form the
955:
929:
925:
921:
918:
868:
864:
854:norepinephrine
829:
826:
796:
792:
788:
784:
780:
776:
772:
769:
721:
717:
713:
709:
702:
691:
688:
686:
683:
659:
656:
561:Arthur Heffter
556:
553:
545:cardiovascular
541:blood pressure
530:biogenic amine
495:phenethylamine
482:
479:
478:
473:
451:
450:
446:standard state
443:
440:
439:
436:
431:
428:
427:
424:
418:
417:
414:
408:
407:
404:
400:
399:
393:
387:
386:
377:
371:
366:
361:
358:
357:
353:
352:
350:
349:
346:
338:
337:
336:
333:
332:
330:
329:
325:
322:
321:
319:
315:
312:
311:
303:
302:
301:
298:
297:
295:
294:
281:
279:
267:
264:
263:
261:
260:
252:
250:
244:
243:
241:
240:
232:
230:
222:
219:
218:
216:
215:
207:
205:
199:
198:
188:
180:
179:
177:
176:
168:
166:
160:
159:
157:
156:
148:
146:
140:
139:
137:
136:
128:
126:
120:
119:
117:
116:
108:
106:
99:
96:
95:
93:
92:
84:
82:
77:
74:
73:
69:
68:
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
13:
10:
9:
6:
4:
3:
2:
6524:
6513:
6510:
6508:
6505:
6503:
6500:
6499:
6497:
6482:
6479:
6477:
6474:
6472:
6471:Thiamphenicol
6469:
6467:
6466:Theodrenaline
6464:
6462:
6459:
6456:
6452:
6449:
6447:
6444:
6442:
6439:
6437:
6434:
6432:
6429:
6427:
6424:
6422:
6419:
6417:
6414:
6412:
6409:
6407:
6404:
6402:
6399:
6397:
6394:
6392:
6389:
6387:
6384:
6382:
6381:Fluorolintane
6379:
6377:
6374:
6372:
6369:
6367:
6364:
6362:
6359:
6357:
6354:
6352:
6349:
6347:
6344:
6342:
6339:
6337:
6334:
6332:
6329:
6327:
6324:
6322:
6319:
6317:
6314:
6312:
6309:
6308:
6306:
6304:Miscellaneous
6302:
6296:
6293:
6291:
6290:Phenylephrine
6288:
6286:
6284:
6280:
6278:
6276:
6272:
6270:
6269:Orciprenaline
6267:
6265:
6262:
6259:
6255:
6252:
6250:
6247:
6244:
6243:Levonordefrin
6240:
6237:
6235:
6232:
6230:
6227:
6225:
6222:
6220:
6217:
6215:
6212:
6210:
6207:
6205:
6203:
6199:
6197:
6191:
6189:
6183:
6180:
6174:
6171:
6165:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
6140:
6138:
6135:
6133:
6130:
6128:
6125:
6123:
6120:
6118:
6115:
6112:
6106:
6104:
6101:
6099:
6096:
6094:
6091:
6089:
6086:
6084:
6081:
6079:
6076:
6075:
6073:
6067:
6063:
6057:
6054:
6052:
6049:
6047:
6044:
6042:
6039:
6037:
6034:
6032:
6029:
6027:
6024:
6022:
6019:
6017:
6014:
6012:
6009:
6007:
6004:
6002:
5999:
5997:
5994:
5992:
5989:
5987:
5984:
5982:
5979:
5977:
5974:
5972:
5969:
5967:
5964:
5961:
5960:
5958:
5956:
5952:
5946:
5943:
5939:
5936:
5934:
5931:
5929:
5926:
5924:
5921:
5919:
5916:
5914:
5911:
5909:
5906:
5904:
5901:
5898:
5897:
5895:
5893:
5889:
5883:
5880:
5878:
5875:
5873:
5870:
5868:
5865:
5863:
5860:
5858:
5855:
5853:
5850:
5846:
5843:
5841:
5838:
5836:
5833:
5831:
5828:
5826:
5823:
5821:
5818:
5816:
5813:
5811:
5810:Methcathinone
5808:
5806:
5803:
5801:
5798:
5796:
5793:
5791:
5788:
5786:
5783:
5781:
5778:
5776:
5773:
5771:
5768:
5766:
5763:
5761:
5758:
5756:
5753:
5751:
5748:
5746:
5743:
5741:
5738:
5736:
5733:
5731:
5728:
5726:
5723:
5721:
5718:
5716:
5713:
5710:
5709:
5707:
5705:
5701:
5695:
5692:
5688:
5685:
5683:
5680:
5676:
5673:
5671:
5668:
5666:
5665:Mephentermine
5663:
5661:
5658:
5656:
5653:
5651:
5648:
5646:
5643:
5640:
5639:
5637:
5635:
5631:
5624:
5617:
5614:
5612:
5609:
5607:
5604:
5602:
5599:
5595:
5592:
5590:
5587:
5585:
5582:
5580:
5577:
5575:
5572:
5570:
5567:
5565:
5562:
5560:
5557:
5555:
5552:
5550:
5547:
5545:
5542:
5540:
5537:
5535:
5532:
5530:
5527:
5525:
5522:
5520:
5517:
5515:
5514:6-Chloro-MDMA
5512:
5510:
5507:
5505:
5502:
5500:
5497:
5495:
5492:
5490:
5487:
5485:
5482:
5480:
5477:
5475:
5472:
5470:
5467:
5465:
5462:
5460:
5457:
5455:
5452:
5450:
5447:
5443:
5440:
5438:
5437:Xylopropamine
5435:
5433:
5430:
5428:
5425:
5423:
5420:
5418:
5415:
5413:
5410:
5408:
5405:
5403:
5400:
5398:
5395:
5393:
5390:
5388:
5385:
5383:
5380:
5378:
5375:
5373:
5370:
5368:
5365:
5363:
5360:
5358:
5355:
5353:
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5333:
5327:
5325:
5322:
5320:
5317:
5315:
5312:
5310:
5307:
5304:
5300:
5297:
5295:
5292:
5290:
5287:
5285:
5282:
5280:
5277:
5275:
5272:
5270:
5267:
5265:
5262:
5260:
5257:
5255:
5252:
5250:
5247:
5245:
5242:
5240:
5237:
5235:
5232:
5229:
5225:
5221:
5218:
5216:
5213:
5211:
5208:
5206:
5203:
5201:
5198:
5196:
5193:
5191:
5188:
5186:
5183:
5181:
5178:
5176:
5175:Benzphetamine
5173:
5171:
5168:
5166:
5163:
5160:
5156:
5152:
5149:
5147:
5144:
5142:
5139:
5137:
5134:
5132:
5129:
5127:
5124:
5122:
5119:
5117:
5114:
5112:
5109:
5105:
5102:
5100:
5097:
5095:
5092:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5067:
5065:
5062:
5060:
5057:
5055:
5052:
5050:
5047:
5045:
5042:
5040:
5037:
5035:
5032:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4967:
4966:Psychedelics:
4964:
4963:
4961:
4959:
4955:
4949:
4946:
4944:
4941:
4937:
4934:
4932:
4929:
4927:
4924:
4921:
4920:
4917:
4914:
4912:
4910:
4906:
4904:
4902:
4898:
4896:
4894:
4890:
4888:
4886:
4882:
4880:
4877:
4875:(amphetamine)
4874:
4871:
4869:
4866:
4864:
4861:
4859:
4856:
4855:
4854:
4853:
4850:
4843:
4840:
4838:
4835:
4833:
4830:
4828:
4825:
4823:
4820:
4818:
4815:
4813:
4810:
4808:
4805:
4803:
4800:
4798:
4797:Isoproscaline
4795:
4793:
4790:
4788:
4785:
4783:
4782:Allylescaline
4780:
4779:
4776:
4773:
4771:
4768:
4766:
4763:
4761:
4758:
4756:
4753:
4751:
4748:
4746:
4743:
4741:
4738:
4736:
4733:
4731:
4728:
4726:
4723:
4721:
4718:
4716:
4713:
4711:
4708:
4706:
4703:
4701:
4698:
4696:
4693:
4691:
4688:
4686:
4683:
4681:
4678:
4676:
4673:
4671:
4668:
4666:
4663:
4661:
4658:
4656:
4653:
4651:
4648:
4646:
4643:
4641:
4638:
4636:
4633:
4631:
4628:
4626:
4623:
4621:
4618:
4616:
4613:
4611:
4608:
4606:
4603:
4601:
4598:
4596:
4593:
4591:
4588:
4586:
4583:
4581:
4578:
4576:
4573:
4571:
4568:
4566:
4563:
4561:
4558:
4556:
4553:
4551:
4548:
4546:
4543:
4541:
4538:
4536:
4533:
4531:
4528:
4526:
4523:
4521:
4518:
4516:
4513:
4511:
4508:
4506:
4503:
4501:
4498:
4496:
4493:
4491:
4488:
4486:
4483:
4481:
4478:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4453:
4452:
4449:
4446:
4444:
4441:
4439:
4436:
4434:
4431:
4429:
4426:
4425:Psychedelics:
4423:
4422:
4420:
4418:
4414:
4410:
4403:
4398:
4396:
4391:
4389:
4384:
4383:
4380:
4369:
4368:
4364:
4360:
4359:Serotonergics
4356:
4355:Dopaminergics
4352:
4348:
4344:
4341:
4334:
4328:
4325:
4323:
4320:
4318:
4315:
4313:
4310:
4308:
4305:
4303:
4300:
4297:
4296:
4293:
4290:
4286:
4283:
4281:
4278:
4277:Agonist-like:
4275:
4272:
4271:
4269:
4265:
4255:
4252:
4250:
4247:
4244:
4243:
4240:
4234:
4231:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4183:
4182:
4179:
4173:
4170:
4168:
4165:
4163:
4160:
4158:
4155:
4153:
4150:
4148:
4145:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4123:
4120:
4118:
4115:
4113:
4110:
4108:
4105:
4102:
4101:
4098:
4092:
4089:
4087:
4084:
4082:
4079:
4077:
4074:
4072:
4069:
4067:
4064:
4062:
4059:
4057:
4054:
4052:
4049:
4047:
4044:
4042:
4039:
4037:
4034:
4032:
4029:
4027:
4024:
4022:
4019:
4017:
4014:
4012:
4009:
4007:
4004:
4002:
3999:
3997:
3994:
3992:
3989:
3987:
3984:
3982:
3979:
3977:
3974:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3954:
3952:
3949:
3947:
3944:
3942:
3939:
3937:
3934:
3932:
3929:
3927:
3924:
3922:
3919:
3917:
3914:
3912:
3909:
3907:
3904:
3902:
3899:
3897:
3894:
3892:
3889:
3887:
3884:
3882:
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3862:
3859:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3794:
3792:
3789:
3786:
3785:
3782:
3776:
3773:
3771:
3768:
3766:
3763:
3761:
3758:
3755:
3754:
3751:
3745:
3742:
3740:
3737:
3735:
3732:
3730:
3727:
3724:
3723:
3720:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3680:Aminoindanes:
3678:
3677:
3674:
3671:
3666:
3660:
3650:
3647:
3644:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3619:Isometheptene
3617:
3615:
3612:
3610:
3609:Hexacyclonate
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3539:
3538:
3535:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3488:
3487:
3484:
3478:
3475:
3473:
3472:Xylopropamine
3470:
3468:
3465:
3463:
3460:
3457:
3450:
3447:
3445:
3442:
3440:
3437:
3435:
3432:
3430:
3428:
3424:
3422:
3419:
3417:
3414:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3394:
3392:
3390:
3386:
3384:
3382:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3350:Methcathinone
3348:
3344:
3341:
3339:
3336:
3335:
3334:
3331:
3329:
3328:Mephentermine
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3137:Benzphetamine
3135:
3133:
3130:
3128:
3125:
3123:
3120:
3116:
3113:
3111:
3108:
3107:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3050:
3049:
3046:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
2999:
2998:
2995:
2989:
2986:
2984:
2983:Phenmetrazine
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2953:
2952:
2949:
2946:
2941:
2935:
2923:
2920:
2919:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2887:Isometheptene
2885:
2883:
2880:
2878:
2877:Hexacyclonate
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2833:
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2802:
2801:
2798:
2792:
2789:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2761:
2760:
2757:
2751:
2748:
2746:
2745:Xylopropamine
2743:
2741:
2738:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2694:
2690:
2688:
2686:
2682:
2680:
2678:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2639:
2637:
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2606:Methcathinone
2604:
2600:
2597:
2595:
2592:
2591:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2510:
2507:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2477:
2475:
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2455:
2452:
2450:
2447:
2445:
2442:
2440:
2439:Benzphetamine
2437:
2435:
2432:
2430:
2427:
2425:
2422:
2420:
2417:
2414:
2411:
2409:
2405:
2402:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2380:
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2349:
2348:
2345:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2306:
2304:
2301:
2298:
2297:
2294:
2288:
2285:
2283:
2282:Phenmetrazine
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2252:
2251:
2248:
2245:
2240:
2234:
2230:
2223:
2218:
2216:
2211:
2209:
2204:
2203:
2200:
2189:
2185:
2181:
2177:
2173:
2169:
2165:
2161:
2154:
2151:
2146:
2142:
2138:
2134:
2130:
2126:
2118:
2115:
2110:
2106:
2102:
2098:
2090:
2087:
2082:
2078:
2074:
2070:
2063:
2060:
2055:
2051:
2047:
2043:
2039:
2035:
2028:
2025:
2020:
2014:
2011:
2006:
2002:
1995:
1988:
1985:
1980:
1976:
1971:
1966:
1962:
1958:
1954:
1947:
1944:
1939:
1935:
1931:
1927:
1923:
1919:
1915:
1911:
1903:
1900:
1895:
1891:
1886:
1881:
1877:
1873:
1869:
1862:
1859:
1854:
1850:
1846:
1842:
1838:
1834:
1830:
1826:
1819:
1817:
1813:
1808:
1804:
1800:
1796:
1792:
1789:(in German).
1788:
1781:
1778:
1773:
1769:
1765:
1761:
1757:
1753:
1746:
1739:
1737:
1733:
1728:
1724:
1720:
1716:
1712:
1709:(in German).
1708:
1701:
1698:
1694:
1691:
1685:
1682:
1678:
1675:
1669:
1667:
1663:
1658:
1654:
1650:
1646:
1639:
1636:
1631:
1627:
1623:
1619:
1612:
1609:
1604:
1600:
1596:
1592:
1585:
1582:
1577:
1573:
1570:: 2193–2197.
1569:
1565:
1561:
1554:
1551:
1548:
1542:
1539:
1533:
1530:
1524:
1521:
1516:
1512:
1508:
1504:
1500:
1496:
1489:
1486:
1481:
1477:
1473:
1467:
1464:
1459:
1455:
1451:
1447:
1443:
1439:
1435:
1431:
1424:
1421:
1415:
1410:
1406:
1402:
1398:
1391:
1389:
1385:
1379:
1374:
1370:
1363:
1361:
1359:
1357:
1355:
1351:
1346:
1339:
1337:
1333:
1328:
1326:9780124695030
1322:
1318:
1314:
1310:
1303:
1300:
1295:
1293:9780124695351
1289:
1285:
1281:
1277:
1270:
1267:
1262:
1258:
1254:
1250:
1249:
1241:
1239:
1237:
1233:
1228:
1224:
1221:(2): 244–54.
1220:
1216:
1209:
1206:
1194:
1190:
1184:
1181:
1176:
1172:
1168:
1164:
1161:(2): 129–54.
1160:
1157:(in German).
1156:
1149:
1146:
1141:
1138:(in French).
1137:
1130:
1127:
1122:
1118:
1111:
1109:
1105:
1098:
1088:
1085:
1078:
1074:
1071:
1069:
1066:
1064:
1061:
1059:
1056:
1054:
1051:
1049:
1046:
1044:
1041:
1039:
1036:
1035:
1031:
1029:
1027:
1023:
1015:
1013:
1011:
1007:
1003:
999:
995:
987:
985:
971:
969:
967:
965:
961:
953:
949:
944:
942:
941:
934:
919:
917:
915:
911:
907:
902:
900:
896:
891:
889:
885:
881:
876:
874:
862:
857:
855:
851:
845:
841:
838:
834:
827:
825:
822:
820:
816:
815:hydrogenation
811:
809:
805:
800:
770:
768:
766:
762:
758:
754:
750:
746:
742:
738:
734:
733:regioisomeric
730:
725:
706:
699:
697:
689:
684:
682:
680:
676:
674:
669:
665:
657:
655:
652:
646:
643:
639:
635:
630:
628:
627:
622:
618:
617:
612:
608:
607:
602:
598:
597:
592:
586:
584:
580:
576:
572:
571:
566:
562:
554:
552:
550:
546:
542:
538:
534:
531:
527:
523:
519:
517:
512:
508:
504:
500:
496:
492:
488:
476:
469:
464:
447:
441:
437:
434:
430:
429:
425:
423:
422:Boiling point
420:
419:
415:
413:
412:Melting point
410:
409:
405:
402:
401:
394:
392:
389:
388:
367:
364:
360:
359:
354:
345:
341:
334:
320:
310:
306:
299:
291:
287:
286:DTXSID2046096
283:
282:
280:
270:
266:
265:
258:
254:
253:
251:
249:
246:
245:
238:
234:
233:
231:
225:
221:
220:
213:
209:
208:
206:
204:
201:
200:
196:
192:
189:
187:
185:ECHA InfoCard
182:
181:
174:
170:
169:
167:
165:
162:
161:
154:
150:
149:
147:
145:
142:
141:
134:
130:
129:
127:
125:
122:
121:
114:
110:
109:
107:
103:
98:
97:
90:
86:
85:
83:
80:
76:
75:
70:
65:
61:
55:
47:
43:
38:
34:
29:
25:
20:
6512:Plant toxins
6461:Solriamfetol
6376:Famprofazone
6282:
6274:
6260:-Octopamine)
6257:
6254:Norfenefrine
6209:Metanephrine
6201:
6157:Isoprenaline
6113:(Dextrodopa)
6098:Adrenochrome
6056:Pyrovalerone
5962:
5941:
5900:Entactogens:
5899:
5849:Entactogens:
5848:
5795:Ethcathinone
5711:
5690:
5679:Entactogens:
5678:
5641:
5634:Phentermines
5597:
5446:Entactogens:
5445:
5442:Zylofuramine
5220:Fenfluramine
5215:Fenethylline
5165:Amphetaminil
5146:Amfepentorex
5107:
4965:
4958:Amphetamines
4939:
4923:Entactogens:
4922:
4908:
4900:
4892:
4884:
4857:
4848:
4846:
4822:Metaescaline
4424:
4339:
4338:
4322:Guanethidine
4298:
4288:
4276:
4273:
4249:Indeloxazine
4245:
4193:4-Methyl-αMT
4188:4-Methyl-αET
4185:Tryptamines:
4184:
4104:Piperazines:
4103:
3936:Fenfluramine
3836:6-Methyl-MDA
3826:5-Methyl-MDA
3791:2-Methyl-MDA
3787:
3756:
3725:
3679:
3594:Feprosidnine
3574:Clofenciclan
3540:
3490:Piperazines:
3489:
3477:Zylofuramine
3426:
3388:
3380:
3246:
3222:Fenethylline
3217:Famprofazone
3202:Ethcathinone
3122:Amphetaminil
3095:Amfepentorex
3051:
3000:
2963:Fenmetramide
2958:Fenbutrazate
2955:Morpholines:
2954:
2862:Feprosidnine
2842:Clofenciclan
2803:
2763:Piperazines:
2762:
2750:Zylofuramine
2692:
2684:
2676:
2548:
2524:Fenethylline
2519:Famprofazone
2499:Ethcathinone
2419:Amphetaminil
2394:Amfepentorex
2350:
2299:
2262:Fenmetramide
2257:Fenbutrazate
2254:Morpholines:
2253:
2163:
2159:
2153:
2128:
2124:
2117:
2100:
2096:
2089:
2072:
2068:
2062:
2037:
2033:
2027:
2018:
2013:
2004:
2000:
1987:
1960:
1956:
1946:
1913:
1909:
1902:
1875:
1871:
1861:
1828:
1824:
1790:
1786:
1780:
1755:
1751:
1710:
1706:
1700:
1692:
1690:Compt. Rend.
1689:
1684:
1676:
1674:Compt. Rend.
1673:
1648:
1644:
1638:
1621:
1617:
1611:
1594:
1590:
1584:
1567:
1563:
1553:
1541:
1532:
1523:
1498:
1494:
1488:
1480:the original
1475:
1466:
1433:
1429:
1423:
1404:
1400:
1368:
1344:
1308:
1302:
1275:
1269:
1252:
1246:
1218:
1214:
1208:
1196:. Retrieved
1192:
1183:
1158:
1154:
1148:
1139:
1136:Compt. Rend.
1135:
1129:
1120:
1116:
1087:
1022:Sinapis alba
1021:
1019:
1009:
1006:H. virescens
1005:
1001:
997:
993:
991:
975:
963:
945:
938:
935:
923:
903:
892:
888:guanethidine
884:vas deferens
877:
858:
846:
842:
839:
835:
831:
828:Pharmacology
823:
819:formaldehyde
812:
807:
803:
801:
774:
756:
726:
707:
700:
693:
672:
663:
661:
658:Biosynthesis
650:
647:
631:
624:
620:
614:
604:
601:proso millet
594:
587:
578:
568:
564:
558:
525:
521:
515:
506:
502:
486:
485:
153:ChEMBL505789
72:Identifiers
63:
59:
57:Other names
6481:Venlafaxine
6446:Pronethalol
6416:Methoxamine
6346:Dizocilpine
6341:Diphenidine
6316:Amidephrine
6277:-Octopamine
6214:Metaraminol
6181:(Droxidopa)
6127:Epinephrine
6117:Dimetofrine
5963:Stimulants:
5942:Stimulants:
5770:Brephedrone
5760:Amfepramone
5712:Stimulants:
5694:Cericlamine
5675:Phentermine
5655:Clortermine
5642:Stimulants:
5422:Sibutramine
5407:Prenylamine
5342:Oxifentorex
5294:Metaraminol
5234:Fenproporex
5205:Fencamfamin
5185:Clobenzorex
5151:Amphetamine
5108:Stimulants:
4849:Stimulants:
4807:Macromerine
4351:Adrenergics
4317:Guanazodine
4302:Bethanidine
4147:Mepiprazole
3941:Flephedrone
3881:Amfepramone
3861:Brephedrone
3757:Oxazolines:
3589:Cyprodenate
3434:Prenylamine
3416:Phentermine
3232:Flephedrone
3227:Fenproporex
3172:Clortermine
3167:Clobenzorex
3105:Amphetamine
3100:Amfepramone
3039:Thozalinone
3019:Cyclazodone
3001:Oxazolines:
2857:Cyprodenate
2720:Prenylamine
2534:Flephedrone
2529:Fenproporex
2469:Clortermine
2464:Clobenzorex
2404:Amphetamine
2399:Amfepramone
2338:Thozalinone
2318:Cyclazodone
2300:Oxazolines:
2019:Merck Index
2007:(2): 83–86.
1198:January 14,
1073:Venlafaxine
1010:H. subflexa
583:Ernst Späth
403:Appearance
356:Properties
191:100.007.920
6496:Categories
6451:Salbutamol
6386:Hexapradol
6366:Etafedrine
6361:Ephenidine
6356:Dopexamine
6351:Dobutamine
6331:Denopamine
6321:Arbutamine
6295:Synephrine
6229:Methyldopa
6224:Metirosine
6172:(Levodopa)
6162:Isoetarine
6147:Fenclonine
6137:Etilefrine
6051:Prolintane
5882:Mephedrone
5845:Radafaxine
5835:Pentedrone
5815:Methedrone
5775:Buphedrone
5765:Benzedrone
5704:Cathinones
5616:Selegiline
5606:Amiflamine
5402:Pholedrine
5352:Ortetamine
5347:Oxilofrine
5279:Lefetamine
5269:Iofetamine
5254:Furfenorex
5249:Formetorex
5239:Flucetorex
5170:Benfluorex
5141:Amfecloral
5136:Alfetamine
5009:D-Deprenyl
4926:Lophophine
4837:Psi-2C-T-4
4832:Proscaline
4802:Jimscaline
4292:SoRI-20041
4285:SoRI-20040
4233:Tryptamine
4016:Methedrone
4011:Mephedrone
3966:Lophophine
3956:Iofetamine
3946:Flucetorex
3846:Amiflamine
3775:Fluminorex
3770:Clominorex
3604:Heptaminol
3599:Gilutensin
3584:Cypenamine
3449:Selegiline
3406:Pholedrine
3375:Ortetamine
3355:Methedrone
3323:Mephedrone
3273:Lophophine
3242:Furfenorex
3147:Buphedrone
3090:Amfecloral
3085:Alfetamine
3029:Fluminorex
3024:Fenozolone
3014:Clominorex
2872:Heptaminol
2867:Gilutensin
2852:Cypenamine
2837:Amineptine
2710:Pholedrine
2700:Pholedrine
2671:Ortetamine
2611:Methedrone
2579:Mephedrone
2569:Lophophine
2544:Furfenorex
2474:D-Deprenyl
2444:Buphedrone
2389:Amfecloral
2384:Alfetamine
2328:Fluminorex
2323:Fenozolone
2313:Clominorex
1378:1957/27227
1371:(Thesis).
1193:erowid.org
1099:References
1063:Pholedrine
960:carcinogen
920:Toxicology
850:adrenergic
696:amphoteric
555:Occurrence
520:, and the
511:derivative
391:Molar mass
257:K3489CA082
164:ChemSpider
133:CHEBI:5764
100:3D model (
79:CAS Number
17:Hordenine
6431:PARGY-LAD
6326:Cafedrine
6285:-Tyramine
6239:Nordefrin
6219:Metaterol
6204:-Tyramine
6196:-Tyrosine
6152:Ibopamine
6041:Naphyrone
5872:Methylone
5840:Pentylone
5785:Cathinone
5780:Bupropion
5623:-Deprenyl
5289:Mefenorex
5259:Gepefrine
5210:Fencamine
5195:Ephedrine
5131:Acridorex
4858:Hordenine
4817:Mescaline
4710:2C-T-22.5
4448:25N-NBOMe
4443:25I-NBOMe
4438:25D-NBOMe
4433:25C-NBOMe
4428:25B-NBOMe
4340:See also:
4312:Guanadrel
4307:Bretylium
4280:SoRI-9804
4254:Viqualine
4208:5-MeO-αMT
4203:5-MeO-αET
4021:Methylone
3734:8-OH-DPAT
3629:Octodrine
3614:Indanorex
3456:-Deprenyl
3360:Methylone
3318:Mefenorex
3247:Hordenine
3197:Ephedrine
3162:Cathinone
2902:Octodrine
2882:Indanorex
2661:Methylone
2574:Mefenorex
2549:Hordenine
2494:Ephedrine
2459:Cathinone
1799:121700602
1175:104408477
1142:: 108–10.
1048:Candicine
771:Synthesis
761:candicine
685:Chemistry
581:) seeds.
487:Hordenine
6436:Phenibut
6122:Dopamine
6103:Ciladopa
6093:a-Me-TRA
5933:Eutylone
5923:Butylone
5867:Ethylone
5862:Butylone
5852:3,4-DMMC
5800:Eutylone
5750:4-MeMABP
5670:Pentorex
5660:Etolorex
5650:Cloforex
5427:Tiflorex
5319:Morforex
5244:Fludorex
4999:Beatrice
4792:Escaline
4327:Guanoxan
4107:2C-B-BZP
3931:Etolorex
3926:Ethylone
3876:Cloforex
3866:Butylone
3765:Aminorex
3493:2C-B-BZP
3467:Tyramine
3462:Tiflorex
3396:Pentorex
3365:Morforex
3237:Fludorex
3207:Ethylone
3152:Butylone
3127:β-Me-PEA
3055:2-OH-PEA
3034:Pemoline
3009:Aminorex
2973:Morforex
2968:Morazone
2766:2C-B-BZP
2740:Tyramine
2735:Tiflorex
2666:Morforex
2539:Fludorex
2509:Ethylone
2449:Butylone
2424:β-Me-PEA
2354:2-OH-PEA
2333:Pemoline
2308:Aminorex
2272:Morforex
2267:Morazone
2180:24248572
1938:14140873
1930:11723224
1894:10344776
1853:10301433
1727:37359919
1695:237-239.
1679:110-113.
1515:14323148
1450:24242721
1255:: 9–18.
1038:Tyramine
1032:See also
880:tyramine
690:Basicity
668:tyramine
533:tyramine
509:-methyl
491:alkaloid
89:539-15-1
50:4-phenol
6507:Phenols
6476:UWA-101
6441:PRO-LAD
6371:ETH-LAD
6132:Epinine
6088:a-Me-DA
6011:4-MePPP
6006:4-MePHP
6001:4-MePBP
5913:Ariadne
5691:Others:
5601:3,4-DCA
5598:Others:
5549:2,3-MDA
5534:6-MAPDB
5499:5-MAPDB
5180:Cathine
5104:ZDCM-04
5089:Psi-DOM
5074:Ganesha
4940:Others:
4755:2C-T-33
4750:2C-T-32
4745:2C-T-31
4740:2C-T-30
4735:2C-T-28
4730:2C-T-27
4725:2C-T-25
4720:2C-T-24
4715:2C-T-23
4705:2C-T-22
4700:2C-T-21
4695:2C-T-20
4690:2C-T-19
4685:2C-T-18
4680:2C-T-17
4675:2C-T-16
4670:2C-T-15
4665:2C-T-14
4660:2C-T-13
4655:2C-T-12
4650:2C-T-11
4645:2C-T-10
4460:2C-B-AN
4246:Others:
4112:3-MeOPP
3541:Others:
3157:Cathine
2804:Others:
2454:Cathine
2188:8193525
2145:5695174
2054:3421887
1845:2570842
1807:8582256
1772:2269269
1458:6435423
1227:5495514
1215:Lloydia
1123:: 6586.
1026:gramine
954:ion, NO
952:nitrite
910:HEK 293
895:gastrin
611:sorghum
503:Hordeum
493:of the
468:what is
466: (
396:165.236
224:PubChem
6391:IP-LAD
6311:AL-LAD
6083:6-OHDA
5618:(also
5611:DiFMDA
5529:6-MAPB
5519:6-EAPB
5509:6-APDB
5494:5-MAPB
5484:5-EAPB
5479:5-APDB
5084:MMDA-2
4984:3C-MAL
4936:MDMPEA
4787:DESOXY
4765:2C-TFM
4760:2C-TFE
4640:2C-T-9
4635:2C-T-8
4630:2C-T-7
4625:2C-T-6
4620:2C-T-5
4615:2C-T-4
4610:2C-T-3
4605:2C-T-2
4580:2C-O-4
4570:2C-NH2
4545:2C-G-N
4540:2C-G-6
4535:2C-G-5
4530:2C-G-4
4525:2C-G-3
4520:2C-G-2
4515:2C-G-1
4267:Others
4167:pTFMPP
4056:4-TFMA
3996:MDMPEA
3831:6-APDB
3821:5-APDB
3451:(also
3303:MDMPEA
3257:5-APDI
2827:5-APDI
2646:MDMPEA
2186:
2178:
2143:
2052:
1979:592104
1977:
1936:
1928:
1892:
1851:
1843:
1805:
1797:
1770:
1725:
1513:
1456:
1448:
1347:: 387.
1323:
1290:
1225:
1173:
950:(e.g.
856:(NE).
751:, and
591:barley
575:barley
499:barley
489:is an
463:verify
460:
340:SMILES
212:C06199
144:ChEMBL
40:Names
6426:MT-45
6179:-DOPS
6170:-DOPA
6111:-DOPA
6078:6-FNE
6021:MOPVP
6016:MOPPP
5991:MDPPP
5986:MDPBP
5981:α-PVP
5976:α-PPP
5971:α-PHP
5966:α-PBP
5908:4-MAB
5903:4-CAB
5857:3-MMC
5755:4-MPD
5745:4-MEC
5740:4-FMC
5735:4-EMC
5730:4-CMC
5725:4-BMC
5715:3-FMC
5687:MDMPH
5584:MMDMA
5564:MDHMA
5504:6-APB
5474:5-APB
5469:4-MTA
5464:4-MMA
5454:4-FMA
5126:3-FMA
5116:2-FMA
5069:DOTFM
5024:DMMDA
5019:DMCPA
4994:Aleph
4974:3C-BZ
4969:3C-AL
4948:DMPEA
4931:MDPEA
4842:TCB-2
4812:MEPEA
4770:2C-YN
4595:2C-SE
4590:2C-Ph
4560:2C-iP
4500:2C-EF
4485:2C-CP
4480:2C-CN
4470:2C-Bu
4465:2C-Bn
4172:TFMPP
4142:MeOPP
4137:MDBZP
4036:MMDMA
4006:MDPEA
3986:MDHMA
3901:DFMDA
3841:AEMMA
3816:4-MTA
3806:4-FMA
3796:4-CAB
3744:MDMAT
3729:6-CAT
3703:MDMAI
3683:5-IAI
3569:5-IAI
3544:2-ADN
3518:MeOPP
3513:MDBZP
3313:MDPEA
3259:(IAP)
3080:4-MMA
3070:4-FMA
3060:4-CAB
3004:4-MAR
2832:5-IAI
2807:2-ADN
2786:MeOPP
2781:MDBZP
2656:MDPEA
2621:MMDMA
2379:4-MMA
2369:4-FMA
2359:4-CAB
2303:4-MAR
2184:S2CID
2141:S2CID
1997:(PDF)
1934:S2CID
1849:S2CID
1748:(PDF)
1723:S2CID
1454:S2CID
1171:S2CID
1079:Notes
873:MAO-A
861:MAO-B
727:The "
651:roots
305:InChI
237:68313
173:61609
124:ChEBI
102:JSmol
6036:MPPP
6031:MPHP
6026:MPBP
5996:MDPV
5938:MBDB
5928:EBDB
5720:4-MC
5682:MDPH
5574:MDOH
5559:MDEA
5524:6-IT
5489:5-IT
5459:4-MA
5449:4-FA
5392:PMMA
5387:PMEA
5372:PFMA
5121:3-FA
5111:2-FA
5099:TeMA
5079:MMDA
5064:DOPR
5044:DOET
5039:DOEF
4989:3C-P
4979:3C-E
4775:2C-V
4600:2C-T
4585:2C-P
4575:2C-O
4565:2C-N
4555:2C-I
4550:2C-H
4510:2C-G
4505:2C-F
4495:2C-E
4490:2C-D
4475:2C-C
4455:2C-B
4213:5-MT
4198:5-CT
4162:pFPP
4157:pCPP
4152:oMPP
4132:mCPP
4127:MBZP
4122:DCPP
4086:PMMA
4081:PMEA
4041:MMMA
4031:MMDA
4001:MDOH
3981:MDEA
3971:MBDB
3921:EDMA
3916:EBDB
3911:DMMA
3811:4-HA
3801:4-FA
3739:MDAT
3708:MMAI
3698:MDAI
3693:ETAI
3688:AMMI
3664:SRAs
3564:4-BP
3559:2-BP
3554:2-AT
3549:2-AI
3528:pFPP
3523:oMPP
3508:mCPP
3503:MBZP
3308:MDOH
3288:MDEA
3278:MBDB
3192:EBDB
3187:DMMA
3075:4-MA
3065:4-FA
2939:NRAs
2822:4-BP
2817:2-AT
2812:2-AI
2791:oMPP
2776:MBZP
2651:MDOH
2636:MDEA
2626:MBDB
2616:MMDA
2504:EBDB
2484:DMMA
2374:4-MA
2364:4-FA
2238:DRAs
2176:PMID
2050:PMID
1975:PMID
1926:PMID
1890:PMID
1841:PMID
1803:PMID
1795:OCLC
1768:PMID
1511:PMID
1446:PMID
1321:ISBN
1288:ISBN
1223:PMID
1200:2021
1000:and
914:cAMP
642:wort
638:beer
634:malt
248:UNII
203:KEGG
6046:PEP
5918:BDB
5820:NEB
5594:TAP
5544:IAP
5539:EDA
5382:PMA
5377:PIA
5367:PFA
5362:PCA
5357:PBA
5314:MMA
5094:TMA
5059:DON
5054:DOM
5049:DOI
5034:DOC
5029:DOB
5014:DMA
4943:BOH
4228:DMT
4223:αMT
4218:αET
4117:BZP
4091:TAP
4076:PMA
4071:pIA
4066:pCA
4061:pBA
4046:NAP
4026:MMA
3951:IAP
3906:DMA
3891:DCA
3856:BOH
3851:BDB
3713:TAI
3498:BZP
3182:DMA
3142:BOH
3132:BDB
2771:BZP
2479:DMA
2434:BOH
2429:BDB
2168:doi
2133:doi
2105:doi
2077:doi
2042:doi
1965:doi
1918:doi
1880:doi
1833:doi
1791:102
1760:doi
1715:doi
1711:186
1693:142
1677:142
1653:doi
1626:doi
1599:doi
1572:doi
1503:doi
1438:doi
1409:doi
1405:238
1373:hdl
1313:doi
1280:doi
1257:doi
1163:doi
1140:142
982:1/2
978:1/2
869:max
799:O.
513:of
274:EPA
227:CID
6498::
5226:,
5157:,
4365:•
4361:•
4357:•
4353:•
4349:•
4345:•
4287:;
3429:IA
3391:CA
3383:BA
2695:IA
2687:CA
2679:BA
2182:.
2174:.
2164:19
2162:.
2139:.
2129:26
2127:.
2101:45
2099:.
2073:40
2071:.
2048:.
2038:65
2036:.
2005:16
2003:.
1999:.
1973:.
1961:97
1932:.
1924:.
1914:60
1912:.
1888:.
1876:34
1874:.
1870:.
1847:.
1839:.
1829:41
1827:.
1815:^
1801:.
1766:.
1756:22
1754:.
1750:.
1735:^
1721:.
1665:^
1649:18
1647:.
1620:.
1595:73
1593:.
1568:95
1566:.
1562:.
1509:.
1497:.
1474:.
1452:.
1444:.
1434:20
1432:.
1403:.
1399:.
1387:^
1353:^
1335:^
1319:.
1286:.
1253:16
1251:.
1235:^
1219:33
1217:.
1191:.
1169:.
1159:40
1121:34
1119:.
1107:^
1012:.
930:50
926:50
924:LD
795:/H
791:SO
787:/H
747:,
743:,
739:,
720:SO
698:.
378:15
372:10
6457:)
6453:(
6283:p
6275:p
6258:m
6256:(
6245:)
6241:(
6202:m
6194:L
6186:L
6177:L
6168:L
6109:D
5625:)
5621:D
5330:L
5305:)
5230:)
5222:(
5161:)
5153:(
4909:p
4901:o
4893:N
4885:m
4401:e
4394:t
4387:v
3645:)
3641:(
3458:)
3454:D
3427:p
3389:p
3381:p
2693:p
2685:p
2677:p
2415:)
2406:(
2221:e
2214:t
2207:v
2190:.
2170::
2147:.
2135::
2111:.
2107::
2083:.
2079::
2056:.
2044::
1981:.
1967::
1940:.
1920::
1896:.
1882::
1855:.
1835::
1809:.
1774:.
1762::
1729:.
1717::
1659:.
1655::
1632:.
1628::
1622:8
1605:.
1601::
1578:.
1574::
1517:.
1505::
1499:8
1460:.
1440::
1417:.
1411::
1381:.
1375::
1329:.
1315::
1296:.
1282::
1263:.
1259::
1229:.
1202:.
1177:.
1165::
964:N
956:2
865:m
808:O
804:p
797:2
793:4
789:2
785:2
781:3
777:5
757:N
722:4
718:2
716:)
714:3
710:3
703:a
673:N
664:N
613:(
603:(
593:(
577:(
526:N
524:,
522:N
516:N
507:N
501:(
458:N
384:O
381:N
375:H
369:C
276:)
272:(
104:)
64:N
62:,
60:N
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