282:
583:. These drugs cause drug-appropriate responses in animals trained to recognize the effects of MDMA, but do not produce responses in animals trained selectively to respond to stimulants or hallucinogens. Because these compounds selectively release serotonin in the brain but have little effect on dopamine or noradrenaline levels, they can produce empathogenic effects but without any stimulant action, instead being somewhat sedating.
49:
40:
555:
623:
derivatives, and mixed compositions of inorganic substances, while generally containing no MDAI. The number of internet searches for MDAI has been considerably higher in the UK compared to
Germany and the USA. MDAI is only non-neurotoxic in isolation but may become neurotoxic when mixed with other
490:
MDAI can be produced from 3-(3,4-methylenedioxyphenyl)propionic acid which is converted to the acid chloride and then heated to produce 5,6-Methylenedioxy-1-indanone. Treatment of the indanone with amyl nitrite in methanol with HCl afforded the hydroxyimino ketone. This is reduced to the
541:
resulted, most significantly serotonin. This result indicates that MDAI is a potent releaser of serotonin, while effectively inhibiting the reuptake of serotonin. For comparison, MDAI is similar in potency with releasing serotonin to MDA but significantly less potent than
1198:
Johnson MP, Frescas SP, Oberlender R, Nichols DE (May 1991). "Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)".
828:
Steele TD, Nichols DE, Yim GK (July 1987). "Stereochemical effects of 3,4-methylenedioxymethamphetamine (MDMA) and related amphetamine derivatives on inhibition of uptake of monoamines into synaptosomes from different regions of rat brain".
1557:
Verordnung des EDI über die
Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Regulation of the EDI about the directories of drugs, psychotropic substances, precursors and auxiliary
1101:
Páleníček T, Lhotková E, Žídková M, Balíková M, Kuchař M, Himl M, et al. (August 2016). "Emerging toxicity of 5,6-methylenedioxy-2-aminoindane (MDAI): Pharmacokinetics, behaviour, thermoregulation and LD50 in rats".
1469:
Corkery JM, Elliott S, Schifano F, Corazza O, Ghodse AH (July 2013). "MDAI (5,6-methylenedioxy-2-aminoindane; 6,7-dihydro-5H-cyclopentabenzodioxol-6-amine; 'sparkle'; 'mindy') toxicity: a brief overview and update".
1234:
Johnson MP, Huang XM, Nichols DE (December 1991). "Serotonin neurotoxicity in rats after combined treatment with a dopaminergic agent followed by a nonneurotoxic 3,4-methylenedioxymethamphetamine (MDMA) analogue".
757:
Nichols DE, Barfknecht CF, Long JP, Standridge RT, Howell HG, Partyka RA, Dyer DC (February 1974). "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)".
586:
Very high doses can be fatal in rats with a 50% fatality rate for those subcutaneously injected with 28 mg/kg of MDAI. This is a result of the way serotonin release interferes with thermoregulation.
566:
produce their effects through multiple mechanisms of action in the body, and consequently produce three distinct cues which animals can be trained to respond to: a stimulant cue typified by drugs such as
942:
Oberlender R, Nichols DE (December 1990). "(+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity".
73:
2214:
793:
Johnson MP, Conarty PF, Nichols DE (July 1991). "monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues".
1383:
Gallagher CT, Assi S, Stair JL, Fergus S, Corazza O, Corkery JM, Schifano F (March 2012). "5,6-Methylenedioxy-2-aminoindane: from laboratory curiosity to 'legal high'".
1774:
907:
Nichols DE (1986). "Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: entactogens".
698:
4394:
722:
Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM (February 1990). "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)".
693:[Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
1340:
Cozzi NV, Frescas S, Marona-Lewicka D, Huang X, Nichols DE (March 1998). "Indan analogs of fenfluramine and norfenfluramine have reduced neurotoxic potential".
109:
595:
MDAI and other similar drugs have been widely used in scientific research, as they are able to replicate many of the effects of MDMA, but without causing the
366:
3835:
4907:
4357:
2207:
2171:
1535:
4928:
4161:
1779:
1013:
Marona-Lewicka D, Nichols DE (June 1994). "Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan".
4899:
4341:
1823:
1764:
1588:
4943:
3980:
3272:
2620:
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4903:
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3186:
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2200:
1811:
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3990:
3297:
2640:
686:
4802:
4646:
4599:
4035:
576:
492:
386:
529:
values of 512 nM, 5,920 nM, and 1,426 nM, respectively. This demonstrates that MDAI has selective affinity for the
4812:
4792:
4462:
3995:
3302:
2645:
1687:
134:
1305:
Sprague JE, Johnson MP, Schmidt CJ, Nichols DE (October 1996). "Studies on the mechanism of p-chloroamphetamine neurotoxicity".
4703:
4501:
4433:
4166:
3687:
2932:
1985:
1682:
155:
94:
4797:
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4361:
4131:
3975:
3538:
3507:
3282:
2801:
2775:
2630:
1754:
1145:
Nichols DE, Johnson MP, Oberlender R (January 1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine".
969:
Oberlender R, Nichols DE (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties".
352:
4787:
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4020:
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2128:
1975:
1828:
1724:
1719:
1692:
1672:
1549:
694:
690:
462:
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came into effect in various countries. Internet-sourced products claimed to be MDAI have been shown variously to contain
4879:
4763:
4337:
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4050:
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3910:
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2423:
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1806:
1627:
261:
611:. It started to be sold online from around 2007, but reached peak popularity between about 2010–2012, after bans on
4832:
3707:
3657:
2176:
2015:
1957:
1605:
1426:
Brandt SD, Sumnall HR, Measham F, Cole J (July 2010). "Second generation mephedrone. The confusing case of NRG-1".
599:
which may be associated with MDMA and some related drugs. No tests have been performed on cardiovascular toxicity.
538:
3121:
2418:
2231:
2223:
1581:
436:
624:
drugs. Three deaths were linked to MDAI use in the UK during 2011–2012, all involving symptoms consistent with
4758:
4457:
4403:
4106:
3905:
3628:
3181:
2901:
2478:
121:
1657:
691:"RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"
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1180:
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1083:
1058:
Kovar KA (July 1998). "Chemistry and pharmacology of hallucinogens, entactogens and stimulants".
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889:
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1111:
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1032:
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838:
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767:
731:
522:
MDAI has been shown to inhibit the reuptake of serotonin, dopamine, and norepinephrine with
421:
298:
230:
185:
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2811:
2724:
2583:
2407:
2271:
1954:
864:
Oberlender R, Nichols DE (1988). "Drug discrimination studies with MDMA and amphetamine".
568:
628:. Two of these also involved other drugs while one death appeared to be from MDAI alone.
491:
2-aminoindan following a modification of
Nichols' earlier method from a paper discussing
281:
17:
3880:
3643:
3573:
3395:
3292:
3206:
2841:
2699:
2578:
2508:
1932:
1278:
Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents".
1353:
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476:
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2317:
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2100:
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1707:
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612:
446:
429:
328:
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3191:
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2543:
2488:
2453:
2105:
2060:
1560:(in German). Das Eidgenössische Departement des Innern (EDI). December 2011.
656:
534:
1491:
1447:
1404:
1123:
579:, and an "entactogen-like" cue which is produced by drugs such as MDAI and
1566:
1361:
1326:
1291:
1256:
1220:
1176:
1079:
1071:
1044:
990:
955:
928:
885:
850:
814:
779:
743:
394:
InChI=1S/C10H11NO2/c11-8-1-6-3-9-10(13-5-12-9)4-7(6)2-8/h3-4,8H,1-2,5,11H2
48:
4666:
4589:
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4511:
4491:
4321:
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3870:
3860:
3759:
3487:
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3456:
3390:
3359:
3231:
3201:
3146:
3028:
3003:
2967:
2962:
2760:
2734:
2729:
2660:
2533:
2503:
2443:
2327:
2302:
2266:
2261:
2085:
2080:
2070:
487:
ring system, which changes its pharmacological properties substantially.
441:
1212:
771:
735:
4486:
4481:
3151:
2448:
2010:
1913:
1901:
1896:
1866:
1861:
1759:
1749:
877:
480:
196:
1439:
3825:
3815:
3251:
2821:
2110:
1908:
1891:
1886:
1881:
1871:
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1851:
1846:
1836:
1789:
1483:
1396:
484:
31:
4772:
4556:
4531:
1516:(in Chinese). China Food and Drug Administration. 27 September 2015
642:
As of
December 2011 MDAI is a controlled substance in Switzerland
4651:
4546:
4030:
3895:
3738:
3723:
3697:
3677:
3563:
2826:
2615:
2032:
2022:
1995:
1970:
1944:
1876:
1841:
1794:
1744:
1739:
553:
473:
470:
351:
342:
4561:
3985:
3915:
3733:
3702:
3287:
2635:
2027:
2005:
2000:
1980:
1920:
1816:
1769:
1699:
1104:
Progress in Neuro-Psychopharmacology & Biological
Psychiatry
651:
580:
563:
543:
523:
417:
128:
4376:
2196:
1570:
554:
39:
1536:"Lists of euphoriant substances subject to control in Denmark"
572:
636:
As of
October 2015 MDAI is a controlled substance in China.
461:
of MDAI is indirectly derived from that of the illicit drug
266:
944:
The
Journal of Pharmacology and Experimental Therapeutics
116:
103:
2933:
1834:
Benzofurans, dihydrobenzofurans and benzothiophenes:
4846:
4675:
4608:
4410:
4261:
3656:
2931:
2230:
2147:
2119:
2041:
1953:
1604:
340:
327:
297:
292:
260:
240:
220:
195:
175:
146:
93:
88:
72:
60:
55:
3658:
537:and MDAI, greater extracellular concentrations of
2232:
639:MDAI is illegal in Denmark as of September 2015.
209:
184:
1538:. The Danish Medicines Agency. September 2015.
717:
715:
571:, a psychedelic cue typified by drugs such as
4388:
2208:
1582:
8:
30:
4395:
4381:
4373:
3667:
2942:
2241:
2215:
2201:
2193:
1589:
1575:
1567:
280:
229:
47:
38:
1158:
1026:
249:
1342:Pharmacology, Biochemistry, and Behavior
1237:Pharmacology, Biochemistry, and Behavior
1147:Pharmacology, Biochemistry, and Behavior
971:Pharmacology, Biochemistry, and Behavior
420:developed in the 1990s by a team led by
2938:Tooltip Norepinephrine releasing agents
678:
391:
371:
276:
160:
479:side chain has been bound back to the
29:
7:
124:(Industrial and scientific use only)
200:
3663:Tooltip Serotonin releasing agents
25:
2237:Tooltip Dopamine releasing agents
1015:European Journal of Pharmacology
795:European Journal of Pharmacology
562:The family of drugs typified by
533:(SERT). In animals treated with
414:5,6-methylenedioxy-2-aminoindane
315:
309:
4908:Monoamine metabolism modulators
4358:Monoamine metabolism modulators
1805:1-Phenylbutan-2-amines: {
701:from the original on 2023-08-27
399:Key:FQDRMHHCWZAXJM-UHFFFAOYSA-N
167:-cyclopenta benzodioxol-6-amine
4929:Drugs not assigned an ATC code
1201:Journal of Medicinal Chemistry
921:10.1080/02791072.1986.10472362
760:Journal of Medicinal Chemistry
724:Journal of Medicinal Chemistry
607:MDAI has been advertised as a
318:
303:
1:
4900:Monoamine reuptake inhibitors
4880:Receptor/signaling modulators
4342:Monoamine reuptake inhibitors
4338:Receptor/signaling modulators
1354:10.1016/s0091-3057(97)00557-1
909:Journal of Psychoactive Drugs
539:monoamine neural transmitters
4294:Adrenergic release blockers:
1514:"关于印发《非药用类麻醉药品和精神药品列管办法》的通知"
1319:10.1016/0006-2952(96)00482-0
1249:10.1016/0091-3057(91)90106-c
1169:10.1016/0091-3057(91)90601-w
1037:10.1016/0014-2999(94)90051-5
983:10.1016/0091-3057(91)90017-V
843:10.1016/0006-2952(87)90594-6
807:10.1016/0014-2999(91)90659-e
4944:Entactogens and empathogens
1116:10.1016/j.pnpbp.2016.04.004
135:Psychoactive Substances Act
4970:
4954:Serotonin releasing agents
4904:Monoamine releasing agents
2224:Monoamine releasing agents
603:Use as a recreational drug
591:Use in scientific research
374:C1C(CC2=CC3=C(C=C21)OCO3)N
293:Chemical and physical data
112:(Prohibited psychotropics)
4949:Monoaminergic neurotoxins
4872:
4764:HHMA (α-methylepinine, α,
4404:Monoaminergic neurotoxins
4330:
4236:
4175:
4094:
3778:
3747:
3716:
3670:
3531:
3480:
3042:
2991:
2945:
2794:
2753:
2341:
2290:
2244:
1280:Drug Design and Discovery
437:serotonin releasing agent
382:
362:
151:
46:
37:
18:Methylenedioxyaminoindane
3629:Phthalimidopropiophenone
2902:Phthalimidopropiophenone
1472:Human Psychopharmacology
1385:Human Psychopharmacology
1307:Biochemical Pharmacology
831:Biochemical Pharmacology
697:(published 2023-07-25).
2157:Substituted amphetamine
1725:3,4-MDA (tenamfetamine)
1706:Phenethylamine: {
1598:Empathogens/entactogens
695:Diário Oficial da União
4759:HHA (α-methyldopamine)
4424:-MPTP (2′-methyl-MPTP)
559:
4803:MDMA (midomafetamine)
4689:-MPTP (2′-amino-MPTP)
4622:-MPTP (2′-amino-MPTP)
4362:Monoamine neurotoxins
3986:MDMA (midomafetamine)
3333:Dextromethamphetamine
3288:MDMA (midomafetamine)
2636:MDMA (midomafetamine)
2589:Dextromethamphetamine
1822:Phentermines: {
1770:MDMA (midomafetamine)
1713:Amphetamines: {
1620:Unfused benzene ring:
1072:10.1055/s-2007-979349
621:substituted cathinone
557:
531:serotonin transporter
4662:Oxidopamine (6-OHDA)
4580:Oxidopamine (6-OHDA)
4570:-Methylnorsalsolinol
3365:Naphthylaminopropane
3247:4-Hydroxyamphetamine
2892:Naphthylaminopropane
2549:4-Hydroxyamphetamine
1938:Naphthylaminopropane
499:catalyst in glacial
4788:MDA (tenamfetamine)
4719:4-CAB (α-ethyl-PCA)
4657:MDA (tenamfetamine)
3971:MDA (tenamfetamine)
3638:Levopropylhexedrine
3416:Phenylpropanolamine
3338:Levomethamphetamine
3278:MDA (tenamfetamine)
3172:Dimethylamphetamine
2983:Pseudophenmetrazine
2917:Levopropylhexedrine
2626:MDA (tenamfetamine)
2594:Levomethamphetamine
2484:Dimethylamphetamine
2282:Pseudophenmetrazine
1213:10.1021/jm00109a020
772:10.1021/jm00248a004
736:10.1021/jm00164a037
558:MDAI in powder form
495:analogues, using a
483:nucleus to form an
449:effects in humans.
428:. It acts as a non-
34:
4768:-dimethyldopamine)
4443:-Cysteinyldopamine
1066:(Suppl 2): 69–72.
1060:Pharmacopsychiatry
878:10.1007/bf00212770
866:Psychopharmacology
626:serotonin syndrome
560:
459:chemical structure
4916:
4915:
4911:
4370:
4369:
4365:
4257:
4256:
3652:
3651:
3434:Propylamphetamine
3258:Iofetamine (123I)
3105:Dextroamphetamine
2927:
2926:
2720:Propylamphetamine
2554:Iofetamine (123I)
2403:Dextroamphetamine
2190:
2189:
1440:10.1136/bmj.c3564
426:Purdue University
407:
406:
353:Interactive image
262:CompTox Dashboard
132:
119:
107:
27:Chemical compound
16:(Redirected from
4961:
4874:
4517:Dopamine quinone
4397:
4390:
4383:
4374:
4332:
4284:Antagonist-like:
3956:Levofenfluramine
3866:Chlorphentermine
3783:Phenethylamines:
3755:4-Methylaminorex
3668:
3664:
3660:
3619:Methylhexanamine
3450:
3406:Phenpromethamine
3263:Lisdexamfetamine
3047:Phenethylamines:
2943:
2939:
2935:
2887:Methylhexanamine
2710:Phenpromethamine
2559:Lisdexamfetamine
2346:Phenethylamines:
2242:
2238:
2234:
2217:
2210:
2203:
2194:
2149:Chemical classes
1591:
1584:
1577:
1568:
1562:
1561:
1554:
1546:
1540:
1539:
1532:
1526:
1525:
1523:
1521:
1510:
1504:
1503:
1484:10.1002/hup.2298
1466:
1460:
1459:
1423:
1417:
1416:
1397:10.1002/hup.1255
1380:
1374:
1373:
1337:
1331:
1330:
1302:
1296:
1295:
1286:(3–4): 299–312.
1275:
1269:
1268:
1231:
1225:
1224:
1195:
1189:
1188:
1162:
1142:
1136:
1135:
1098:
1092:
1091:
1055:
1049:
1048:
1030:
1010:
1004:
1002:
966:
960:
959:
939:
933:
932:
904:
898:
897:
861:
855:
854:
837:(14): 2297–303.
825:
819:
818:
790:
784:
783:
754:
748:
747:
719:
710:
709:
707:
706:
683:
465:, but the alpha-
422:David E. Nichols
355:
335:
320:
317:
311:
305:
285:
284:
270:
268:
253:
233:
213:
203:
202:
188:
139:Illegal in China
130:
127:
118:
115:
105:
102:
51:
42:
35:
33:
21:
4969:
4968:
4964:
4963:
4962:
4960:
4959:
4958:
4919:
4918:
4917:
4912:
4868:
4842:
4818:Norfenfluramine
4808:Methamphetamine
4688:
4671:
4621:
4604:
4557:MPP (cyperquat)
4552:Methamphetamine
4463:ALDH inhibitors
4423:
4406:
4401:
4371:
4366:
4326:
4269:DAT modulators:
4253:
4232:
4171:
4090:
4046:Norfenfluramine
3891:Dexfenfluramine
3774:
3743:
3721:Aminotetralins:
3712:
3662:
3648:
3634:Propylhexedrine
3527:
3476:
3448:
3439:Pseudoephedrine
3328:Methamphetamine
3110:Levoamphetamine
3038:
2987:
2973:Phendimetrazine
2937:
2923:
2912:Propylhexedrine
2907:Phenylbiguanide
2790:
2749:
2725:Pseudoephedrine
2584:Methamphetamine
2408:Levoamphetamine
2337:
2286:
2272:Phendimetrazine
2236:
2226:
2221:
2191:
2186:
2182:Sub. tryptamine
2162:Sub. benzofuran
2143:
2115:
2037:
2020:Aminotetralins:
2018:
1959:
1949:
1940:
1928:
1916:
1904:
1832:
1702:
1695:
1612:
1610:
1607:
1600:
1595:
1565:
1552:
1548:
1547:
1543:
1534:
1533:
1529:
1519:
1517:
1512:
1511:
1507:
1468:
1467:
1463:
1425:
1424:
1420:
1382:
1381:
1377:
1339:
1338:
1334:
1304:
1303:
1299:
1277:
1276:
1272:
1233:
1232:
1228:
1197:
1196:
1192:
1144:
1143:
1139:
1100:
1099:
1095:
1057:
1056:
1052:
1028:10.1.1.688.1895
1012:
1011:
1007:
968:
967:
963:
950:(3): 1098–106.
941:
940:
936:
906:
905:
901:
863:
862:
858:
827:
826:
822:
792:
791:
787:
756:
755:
751:
721:
720:
713:
704:
702:
685:
684:
680:
676:
668:
664:
660:
648:
634:
605:
593:
569:methamphetamine
552:
527:
520:
512:
508:
503:with catalytic
455:
403:
400:
395:
390:
389:
378:
375:
370:
369:
358:
333:
323:
314:
308:
288:
264:
256:
236:
216:
199:
191:
171:
168:
159:
158:
142:
84:
63:
28:
23:
22:
15:
12:
11:
5:
4967:
4965:
4957:
4956:
4951:
4946:
4941:
4939:Designer drugs
4936:
4931:
4921:
4920:
4914:
4913:
4873:
4870:
4869:
4867:
4866:
4861:
4856:
4850:
4848:
4844:
4843:
4841:
4840:
4835:
4830:
4825:
4820:
4815:
4810:
4805:
4800:
4795:
4790:
4785:
4780:
4775:
4770:
4761:
4756:
4751:
4746:
4741:
4736:
4731:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4691:
4686:
4681:
4679:
4673:
4672:
4670:
4669:
4664:
4659:
4654:
4649:
4644:
4639:
4634:
4629:
4624:
4619:
4614:
4612:
4606:
4605:
4603:
4602:
4597:
4592:
4587:
4582:
4577:
4572:
4564:
4559:
4554:
4549:
4544:
4539:
4534:
4529:
4524:
4519:
4514:
4509:
4504:
4499:
4494:
4489:
4484:
4479:
4474:
4460:
4458:6-OHDA quinone
4455:
4450:
4445:
4436:
4431:
4426:
4421:
4416:
4414:
4408:
4407:
4402:
4400:
4399:
4392:
4385:
4377:
4368:
4367:
4331:
4328:
4327:
4325:
4324:
4319:
4314:
4309:
4304:
4299:
4290:
4289:
4277:
4265:
4263:
4259:
4258:
4255:
4254:
4252:
4251:
4246:
4237:
4234:
4233:
4231:
4230:
4225:
4220:
4215:
4210:
4205:
4200:
4195:
4190:
4185:
4176:
4173:
4172:
4170:
4169:
4164:
4159:
4154:
4149:
4144:
4139:
4134:
4129:
4124:
4119:
4114:
4109:
4104:
4095:
4092:
4091:
4089:
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:
3883:
3881:Metamfepramone
3878:
3873:
3868:
3863:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3803:
3798:
3793:
3788:
3779:
3776:
3775:
3773:
3772:
3767:
3762:
3757:
3748:
3745:
3744:
3742:
3741:
3736:
3731:
3726:
3717:
3714:
3713:
3711:
3710:
3705:
3700:
3695:
3690:
3685:
3680:
3671:
3665:
3654:
3653:
3650:
3649:
3647:
3646:
3644:Tuaminoheptane
3641:
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3574:Cyclopentamine
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3532:
3529:
3528:
3526:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3481:
3478:
3477:
3475:
3474:
3469:
3464:
3459:
3454:
3441:
3436:
3431:
3426:
3418:
3413:
3408:
3403:
3398:
3396:Phenethylamine
3393:
3388:
3380:
3372:
3367:
3362:
3357:
3352:
3347:
3342:
3341:
3340:
3335:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3293:Metamfepramone
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3249:
3244:
3239:
3234:
3229:
3224:
3219:
3214:
3209:
3207:Etilamfetamine
3204:
3199:
3194:
3189:
3184:
3179:
3174:
3169:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3114:
3113:
3112:
3107:
3097:
3092:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3043:
3040:
3039:
3037:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2992:
2989:
2988:
2986:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2946:
2940:
2929:
2928:
2925:
2924:
2922:
2921:
2920:
2919:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2842:Cyclopentamine
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2804:
2795:
2792:
2791:
2789:
2788:
2783:
2778:
2773:
2768:
2763:
2754:
2751:
2750:
2748:
2747:
2742:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2700:Phenethylamine
2697:
2692:
2684:
2676:
2668:
2663:
2658:
2653:
2648:
2643:
2638:
2633:
2628:
2623:
2618:
2613:
2608:
2603:
2598:
2597:
2596:
2591:
2581:
2579:Metamfepramone
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2536:
2531:
2526:
2521:
2516:
2511:
2509:Etilamfetamine
2506:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2441:
2436:
2431:
2426:
2421:
2416:
2411:
2405:
2396:
2391:
2386:
2381:
2376:
2371:
2366:
2361:
2356:
2351:
2342:
2339:
2338:
2336:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2300:
2291:
2288:
2287:
2285:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2245:
2239:
2228:
2227:
2222:
2220:
2219:
2212:
2205:
2197:
2188:
2187:
2185:
2184:
2179:
2174:
2169:
2167:Sub. cathinone
2164:
2159:
2153:
2151:
2145:
2144:
2142:
2141:
2136:
2131:
2125:
2123:
2117:
2116:
2114:
2113:
2108:
2103:
2098:
2093:
2088:
2083:
2078:
2073:
2068:
2063:
2058:
2053:
2047:
2045:
2039:
2038:
2036:
2035:
2030:
2025:
2013:
2008:
2003:
1998:
1993:
1988:
1983:
1978:
1973:
1964:
1962:
1951:
1950:
1948:
1947:
1935:
1933:Methamnetamine
1923:
1911:
1899:
1894:
1889:
1884:
1879:
1874:
1869:
1864:
1859:
1854:
1849:
1844:
1839:
1826:
1820:
1814:
1809:
1803:
1797:
1792:
1787:
1782:
1777:
1772:
1767:
1762:
1757:
1752:
1747:
1742:
1737:
1732:
1727:
1722:
1717:
1711:
1704:Benzodioxoles:
1690:
1685:
1680:
1675:
1670:
1665:
1660:
1655:
1650:
1645:
1640:
1635:
1630:
1625:
1616:
1614:
1602:
1601:
1596:
1594:
1593:
1586:
1579:
1571:
1564:
1563:
1541:
1527:
1505:
1461:
1418:
1375:
1332:
1297:
1270:
1226:
1190:
1160:10.1.1.670.504
1137:
1093:
1050:
1005:
961:
934:
899:
856:
820:
785:
749:
711:
689:(2023-07-24).
677:
675:
672:
671:
670:
666:
662:
658:
654:
647:
644:
633:
630:
604:
601:
592:
589:
551:
548:
525:
519:
516:
510:
506:
454:
451:
405:
404:
402:
401:
398:
396:
393:
385:
384:
383:
380:
379:
377:
376:
373:
365:
364:
363:
360:
359:
357:
356:
348:
346:
338:
337:
331:
325:
324:
321:
312:
306:
301:
295:
294:
290:
289:
287:
286:
278:DTXSID60157741
273:
271:
258:
257:
255:
254:
246:
244:
238:
237:
235:
234:
226:
224:
218:
217:
215:
214:
206:
204:
193:
192:
190:
189:
181:
179:
173:
172:
170:
169:
162:
154:
153:
152:
149:
148:
144:
143:
141:
140:
137:
125:
113:
99:
97:
91:
90:
86:
85:
83:
82:
78:
76:
70:
69:
66:
64:administration
58:
57:
53:
52:
44:
43:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4966:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4934:Benzodioxoles
4932:
4930:
4927:
4926:
4924:
4910:
4909:
4905:
4901:
4897:
4896:Serotonergics
4893:
4892:Melatonergics
4889:
4888:Dopaminergics
4885:
4881:
4878:
4871:
4865:
4862:
4860:
4857:
4855:
4852:
4851:
4849:
4845:
4839:
4836:
4834:
4831:
4829:
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4767:
4762:
4760:
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4740:
4737:
4735:
4732:
4730:
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4683:
4682:
4680:
4678:
4674:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4650:
4648:
4645:
4643:
4642:6-Hydroxydopa
4640:
4638:
4635:
4633:
4630:
4628:
4625:
4623:
4616:
4615:
4613:
4611:
4610:Noradrenergic
4607:
4601:
4598:
4596:
4593:
4591:
4588:
4586:
4583:
4581:
4578:
4576:
4575:Norsalsolinol
4573:
4571:
4569:
4565:
4563:
4560:
4558:
4555:
4553:
4550:
4548:
4545:
4543:
4540:
4538:
4535:
4533:
4530:
4528:
4525:
4523:
4522:Fenpropathrin
4520:
4518:
4515:
4513:
4510:
4508:
4507:DOPAL quinone
4505:
4503:
4500:
4498:
4495:
4493:
4490:
4488:
4485:
4483:
4480:
4478:
4475:
4472:
4471:methylmercury
4468:
4464:
4461:
4459:
4456:
4454:
4453:6-Hydroxydopa
4451:
4449:
4446:
4444:
4442:
4437:
4435:
4432:
4430:
4427:
4425:
4418:
4417:
4415:
4413:
4409:
4405:
4398:
4393:
4391:
4386:
4384:
4379:
4378:
4375:
4364:
4363:
4359:
4355:
4354:Serotonergics
4351:
4350:Dopaminergics
4347:
4343:
4339:
4336:
4329:
4323:
4320:
4318:
4315:
4313:
4310:
4308:
4305:
4303:
4300:
4298:
4295:
4292:
4291:
4288:
4285:
4281:
4278:
4276:
4273:
4272:Agonist-like:
4270:
4267:
4266:
4264:
4260:
4250:
4247:
4245:
4242:
4239:
4238:
4235:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4178:
4177:
4174:
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:
4103:
4100:
4097:
4096:
4093:
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:
3787:
3784:
3781:
3780:
3777:
3771:
3768:
3766:
3763:
3761:
3758:
3756:
3753:
3750:
3749:
3746:
3740:
3737:
3735:
3732:
3730:
3727:
3725:
3722:
3719:
3718:
3715:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3675:Aminoindanes:
3673:
3672:
3669:
3666:
3661:
3655:
3645:
3642:
3639:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3614:Isometheptene
3612:
3610:
3607:
3605:
3604:Hexacyclonate
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:
3540:
3537:
3534:
3533:
3530:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3483:
3482:
3479:
3473:
3470:
3468:
3467:Xylopropamine
3465:
3463:
3460:
3458:
3455:
3452:
3445:
3442:
3440:
3437:
3435:
3432:
3430:
3427:
3425:
3423:
3419:
3417:
3414:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3394:
3392:
3389:
3387:
3385:
3381:
3379:
3377:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3346:
3345:Methcathinone
3343:
3339:
3336:
3334:
3331:
3330:
3329:
3326:
3324:
3323:Mephentermine
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:
3259:
3256:
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:
3135:
3133:
3132:Benzphetamine
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3111:
3108:
3106:
3103:
3102:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3045:
3044:
3041:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2994:
2993:
2990:
2984:
2981:
2979:
2978:Phenmetrazine
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2948:
2947:
2944:
2941:
2936:
2930:
2918:
2915:
2914:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2882:Isometheptene
2880:
2878:
2875:
2873:
2872:Hexacyclonate
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:
2803:
2800:
2797:
2796:
2793:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2762:
2759:
2756:
2755:
2752:
2746:
2743:
2741:
2740:Xylopropamine
2738:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2689:
2685:
2683:
2681:
2677:
2675:
2673:
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:
2604:
2602:
2601:Methcathinone
2599:
2595:
2592:
2590:
2587:
2586:
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:
2437:
2435:
2434:Benzphetamine
2432:
2430:
2427:
2425:
2422:
2420:
2417:
2415:
2412:
2409:
2406:
2404:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2380:
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2350:
2347:
2344:
2343:
2340:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2306:
2304:
2301:
2299:
2296:
2293:
2292:
2289:
2283:
2280:
2278:
2277:Phenmetrazine
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2247:
2246:
2243:
2240:
2235:
2229:
2225:
2218:
2213:
2211:
2206:
2204:
2199:
2198:
2195:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2154:
2152:
2150:
2146:
2140:
2137:
2135:
2132:
2130:
2127:
2126:
2124:
2122:
2118:
2112:
2109:
2107:
2104:
2102:
2099:
2097:
2094:
2092:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2072:
2069:
2067:
2064:
2062:
2059:
2057:
2054:
2052:
2049:
2048:
2046:
2044:
2040:
2034:
2031:
2029:
2026:
2024:
2021:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1968:Aminoindanes:
1966:
1965:
1963:
1961:
1956:
1952:
1946:
1943:
1939:
1936:
1934:
1931:
1930:Naphthalenes:
1927:
1924:
1922:
1919:
1915:
1912:
1910:
1907:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1845:
1843:
1840:
1838:
1835:
1830:
1827:
1825:
1821:
1818:
1815:
1813:
1810:
1808:
1804:
1801:
1798:
1796:
1793:
1791:
1788:
1786:
1783:
1781:
1778:
1776:
1773:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1746:
1743:
1741:
1738:
1736:
1733:
1731:
1728:
1726:
1723:
1721:
1718:
1716:
1712:
1709:
1705:
1701:
1698:
1697:Benzodioxine:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1671:
1669:
1666:
1664:
1661:
1659:
1656:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1618:
1617:
1615:
1609:
1603:
1599:
1592:
1587:
1585:
1580:
1578:
1573:
1572:
1569:
1559:
1551:
1545:
1542:
1537:
1531:
1528:
1515:
1509:
1506:
1501:
1497:
1493:
1489:
1485:
1481:
1478:(4): 345–55.
1477:
1473:
1465:
1462:
1457:
1453:
1449:
1445:
1441:
1437:
1433:
1429:
1422:
1419:
1414:
1410:
1406:
1402:
1398:
1394:
1391:(2): 106–12.
1390:
1386:
1379:
1376:
1371:
1367:
1363:
1359:
1355:
1351:
1348:(3): 709–15.
1347:
1343:
1336:
1333:
1328:
1324:
1320:
1316:
1313:(8): 1271–7.
1312:
1308:
1301:
1298:
1293:
1289:
1285:
1281:
1274:
1271:
1266:
1262:
1258:
1254:
1250:
1246:
1243:(4): 915–22.
1242:
1238:
1230:
1227:
1222:
1218:
1214:
1210:
1207:(5): 1662–8.
1206:
1202:
1194:
1191:
1186:
1182:
1178:
1174:
1170:
1166:
1161:
1156:
1152:
1148:
1141:
1138:
1133:
1129:
1125:
1121:
1117:
1113:
1109:
1105:
1097:
1094:
1089:
1085:
1081:
1077:
1073:
1069:
1065:
1061:
1054:
1051:
1046:
1042:
1038:
1034:
1029:
1024:
1021:(1–2): 1–13.
1020:
1016:
1009:
1006:
1000:
996:
992:
988:
984:
980:
976:
972:
965:
962:
957:
953:
949:
945:
938:
935:
930:
926:
922:
918:
915:(4): 305–13.
914:
910:
903:
900:
895:
891:
887:
883:
879:
875:
871:
867:
860:
857:
852:
848:
844:
840:
836:
832:
824:
821:
816:
812:
808:
804:
800:
796:
789:
786:
781:
777:
773:
769:
765:
761:
753:
750:
745:
741:
737:
733:
730:(2): 703–10.
729:
725:
718:
716:
712:
700:
696:
692:
688:
682:
679:
673:
669:
655:
653:
650:
649:
645:
643:
640:
637:
631:
629:
627:
622:
618:
614:
610:
609:designer drug
602:
600:
598:
597:neurotoxicity
590:
588:
584:
582:
578:
574:
570:
565:
556:
549:
547:
545:
540:
536:
532:
528:
517:
515:
513:
502:
498:
494:
488:
486:
482:
478:
475:
472:
468:
464:
460:
452:
450:
448:
445:and produces
444:
443:
438:
435:
431:
427:
423:
419:
415:
411:
397:
392:
388:
381:
372:
368:
361:
354:
350:
349:
347:
344:
339:
332:
330:
326:
302:
300:
296:
291:
283:
279:
275:
274:
272:
263:
259:
252:
248:
247:
245:
243:
239:
232:
228:
227:
225:
223:
219:
212:
208:
207:
205:
198:
194:
187:
183:
182:
180:
178:
174:
166:
163:6,7-Dihydro-5
161:
157:
150:
145:
138:
136:
126:
123:
114:
111:
101:
100:
98:
96:
92:
87:
80:
79:
77:
75:
71:
67:
65:
59:
56:Clinical data
54:
50:
45:
41:
36:
19:
4876:
4875:
4765:
4749:Fenfluramine
4677:Serotonergic
4567:
4497:DOPA quinone
4440:
4412:Dopaminergic
4334:
4333:
4317:Guanethidine
4293:
4283:
4271:
4268:
4244:Indeloxazine
4240:
4188:4-Methyl-αMT
4183:4-Methyl-αET
4180:Tryptamines:
4179:
4099:Piperazines:
4098:
3931:Fenfluramine
3831:6-Methyl-MDA
3821:5-Methyl-MDA
3786:2-Methyl-MDA
3782:
3751:
3720:
3692:
3674:
3589:Feprosidnine
3569:Clofenciclan
3535:
3485:Piperazines:
3484:
3472:Zylofuramine
3421:
3383:
3375:
3217:Fenethylline
3212:Famprofazone
3197:Ethcathinone
3117:Amphetaminil
3090:Amfepentorex
3046:
2995:
2958:Fenmetramide
2953:Fenbutrazate
2950:Morpholines:
2949:
2857:Feprosidnine
2837:Clofenciclan
2798:
2758:Piperazines:
2757:
2745:Zylofuramine
2687:
2679:
2671:
2519:Fenethylline
2514:Famprofazone
2494:Ethcathinone
2414:Amphetaminil
2389:Amfepentorex
2345:
2294:
2257:Fenmetramide
2252:Fenbutrazate
2249:Morpholines:
2248:
2129:4-Methyl-αET
2019:
1990:
1967:
1941:
1929:
1917:
1905:
1833:
1800:N-t-BOC-MDMA
1735:6-Methyl-MDA
1730:5-Methyl-MDA
1715:2-Methyl-MDA
1703:
1696:
1668:Metaescaline
1619:
1606:Phenylalkyl-
1556:
1550:"812.121.11"
1544:
1530:
1518:. Retrieved
1508:
1475:
1471:
1464:
1431:
1427:
1421:
1388:
1384:
1378:
1345:
1341:
1335:
1310:
1306:
1300:
1283:
1279:
1273:
1240:
1236:
1229:
1204:
1200:
1193:
1153:(1): 135–9.
1150:
1146:
1140:
1107:
1103:
1096:
1063:
1059:
1053:
1018:
1014:
1008:
977:(3): 581–6.
974:
970:
964:
947:
943:
937:
912:
908:
902:
869:
865:
859:
834:
830:
823:
798:
794:
788:
766:(2): 161–6.
763:
759:
752:
727:
723:
703:. Retrieved
681:
641:
638:
635:
632:Legal Status
606:
594:
585:
561:
521:
518:Pharmacology
489:
467:methyl group
456:
440:
413:
409:
408:
164:
133: Under
95:Legal status
89:Legal status
4884:Adrenergics
4754:Haloperidol
4527:Haloperidol
4477:Amphetamine
4346:Adrenergics
4312:Guanazodine
4297:Bethanidine
4142:Mepiprazole
3936:Flephedrone
3876:Amfepramone
3856:Brephedrone
3752:Oxazolines:
3584:Cyprodenate
3429:Prenylamine
3411:Phentermine
3227:Flephedrone
3222:Fenproporex
3167:Clortermine
3162:Clobenzorex
3100:Amphetamine
3095:Amfepramone
3034:Thozalinone
3014:Cyclazodone
2996:Oxazolines:
2852:Cyprodenate
2715:Prenylamine
2529:Flephedrone
2524:Fenproporex
2464:Clortermine
2459:Clobenzorex
2399:Amphetamine
2394:Amfepramone
2333:Thozalinone
2313:Cyclazodone
2295:Oxazolines:
2121:Tryptamines
2091:Flephedrone
2076:Dimethylone
2066:Brephedrone
1960:alkylamines
1613:cathinones)
1611:(other than
872:(1): 71–6.
801:(1): 9–16.
501:acetic acid
477:amphetamine
432:and highly
336: g·mol
186:132741-81-2
147:Identifiers
4923:Categories
4704:2,4,5-THMA
4595:Salsolinol
4467:disulfiram
4434:2,4,5-THMA
4287:SoRI-20041
4280:SoRI-20040
4228:Tryptamine
4011:Methedrone
4006:Mephedrone
3961:Lophophine
3951:Iofetamine
3941:Flucetorex
3841:Amiflamine
3770:Fluminorex
3765:Clominorex
3599:Heptaminol
3594:Gilutensin
3579:Cypenamine
3444:Selegiline
3401:Pholedrine
3370:Ortetamine
3350:Methedrone
3318:Mephedrone
3268:Lophophine
3237:Furfenorex
3142:Buphedrone
3085:Amfecloral
3080:Alfetamine
3024:Fluminorex
3019:Fenozolone
3009:Clominorex
2867:Heptaminol
2862:Gilutensin
2847:Cypenamine
2832:Amineptine
2705:Pholedrine
2695:Pholedrine
2666:Ortetamine
2606:Methedrone
2574:Mephedrone
2564:Lophophine
2539:Furfenorex
2469:D-Deprenyl
2439:Buphedrone
2384:Amfecloral
2379:Alfetamine
2323:Fluminorex
2318:Fenozolone
2308:Clominorex
2172:Sub. MDPEA
2101:Methedrone
2096:Mephedrone
2043:Cathinones
1708:Lophophine
1558:chemicals)
705:2023-08-27
674:References
617:mephedrone
613:mephedrone
447:entactogen
430:neurotoxic
341:3D model (
329:Molar mass
251:0DMJ6G3XBF
222:ChemSpider
177:CAS Number
156:IUPAC name
4877:See also:
4699:2,4,5-THA
4627:2,4,5-THA
4429:2,4,5-THA
4335:See also:
4307:Guanadrel
4302:Bretylium
4275:SoRI-9804
4249:Viqualine
4203:5-MeO-αMT
4198:5-MeO-αET
4016:Methylone
3729:8-OH-DPAT
3624:Octodrine
3609:Indanorex
3451:-Deprenyl
3355:Methylone
3313:Mefenorex
3242:Hordenine
3192:Ephedrine
3157:Cathinone
2897:Octodrine
2877:Indanorex
2656:Methylone
2569:Mefenorex
2544:Hordenine
2489:Ephedrine
2454:Cathinone
2106:Methylone
2061:BK-5-MAPB
1942:Tetralin:
1658:4,4'-DMAR
1520:1 October
1434:: c3564.
1413:205924978
1155:CiteSeerX
1110:: 49–59.
1023:CiteSeerX
619:or other
535:reserpine
453:Chemistry
434:selective
62:Routes of
4847:Unsorted
4667:Xylamine
4590:Rotenone
4585:Paraquat
4542:Mancozeb
4512:Dopamine
4492:Dieldrin
4322:Guanoxan
4102:2C-B-BZP
3926:Etolorex
3921:Ethylone
3871:Cloforex
3861:Butylone
3760:Aminorex
3488:2C-B-BZP
3462:Tyramine
3457:Tiflorex
3391:Pentorex
3360:Morforex
3232:Fludorex
3202:Ethylone
3147:Butylone
3122:β-Me-PEA
3050:2-OH-PEA
3029:Pemoline
3004:Aminorex
2968:Morforex
2963:Morazone
2761:2C-B-BZP
2735:Tyramine
2730:Tiflorex
2661:Morforex
2534:Fludorex
2504:Ethylone
2444:Butylone
2419:β-Me-PEA
2349:2-OH-PEA
2328:Pemoline
2303:Aminorex
2267:Morforex
2262:Morazone
2177:Sub. PEA
2086:Eutylone
2081:Ethylone
2071:Butylone
1955:Cyclized
1918:Indoles:
1906:Indanes:
1500:12322724
1492:23881883
1456:20354123
1448:20605894
1405:22389075
1370:41048219
1185:20485505
1132:33032545
1124:27083855
1088:28388528
999:19069907
894:19664637
699:Archived
646:See also
442:in vitro
110:Class F2
74:ATC code
4734:5,7-DHT
4729:5,6-DHT
4714:3,4-DCA
4694:2,4-DCA
4647:DOPEGAL
4637:5,7-DHT
4632:5,6-DHT
4487:Daidzin
4482:Benomyl
4465:(e.g.,
4448:5,6-DHT
4241:Others:
4107:3-MeOPP
3536:Others:
3152:Cathine
2799:Others:
2449:Cathine
2011:NM-2-AI
1958:phenyl-
1914:5-MAPDI
1902:IBF5MAP
1897:6-MAPDB
1867:5-MAPBT
1862:5-MAPDB
1831: }
1819: }
1802: }
1760:Lys-MDA
1750:DMMDA-2
1720:2,3-MDA
1710: }
1663:Ariadne
1362:9512076
1327:8937435
1292:8400010
1265:7199902
1257:1726189
1221:1674539
1177:1826785
1080:9754836
1045:7925587
991:2068194
956:1979813
929:2880944
886:2898791
851:2886126
815:1685125
780:4809251
744:1967651
550:Effects
481:benzene
469:of the
439:(SSRA)
416:) is a
334:177.203
299:Formula
197:PubChem
120::
4854:5-HIAL
4262:Others
4162:pTFMPP
4051:4-TFMA
3991:MDMPEA
3826:6-APDB
3816:5-APDB
3446:(also
3298:MDMPEA
3252:5-APDI
2822:5-APDI
2641:MDMPEA
2111:TH-PVP
1909:5-APDI
1892:6-MAPB
1887:6-EAPB
1882:6-APDB
1872:5-MBPB
1857:5-MAPB
1852:5-EAPB
1847:5-APDB
1837:2-MAPB
1790:MMDA-2
1608:amines
1498:
1490:
1454:
1446:
1411:
1403:
1368:
1360:
1325:
1290:
1263:
1255:
1219:
1183:
1175:
1157:
1130:
1122:
1086:
1078:
1043:
1025:
997:
989:
954:
927:
892:
884:
849:
813:
778:
742:
687:Anvisa
485:indane
367:SMILES
231:111694
211:125558
108:
4864:RHPTP
4724:5-IAI
4685:2′-NH
4652:DSP-4
4618:2′-NH
4600:Ziram
4547:Maneb
4502:DOPAL
4420:2′-CH
4167:TFMPP
4137:MeOPP
4132:MDBZP
4031:MMDMA
4001:MDPEA
3981:MDHMA
3896:DFMDA
3836:AEMMA
3811:4-MTA
3801:4-FMA
3791:4-CAB
3739:MDMAT
3724:6-CAT
3698:MDMAI
3678:5-IAI
3564:5-IAI
3539:2-ADN
3513:MeOPP
3508:MDBZP
3308:MDPEA
3254:(IAP)
3075:4-MMA
3065:4-FMA
3055:4-CAB
2999:4-MAR
2827:5-IAI
2802:2-ADN
2781:MeOPP
2776:MDBZP
2651:MDPEA
2616:MMDMA
2374:4-MMA
2364:4-FMA
2354:4-CAB
2298:4-MAR
2056:4-EMC
2051:3-MMC
2033:MDMAT
2023:6-CAT
1996:MDMAI
1971:5-IAI
1945:6-APT
1926:6-API
1877:6-APB
1842:5-APB
1795:MMDMA
1775:MDMOH
1745:DMMDA
1740:DFMDA
1653:4-MTA
1648:4-FMA
1643:4-MMA
1628:4-CAB
1623:3-CMA
1553:(PDF)
1496:S2CID
1452:S2CID
1409:S2CID
1366:S2CID
1261:S2CID
1181:S2CID
1128:S2CID
1084:S2CID
995:S2CID
890:S2CID
474:amino
471:alkyl
387:InChI
343:JSmol
4859:RHPP
4833:PCMA
4813:MMAI
4798:MDEA
4793:MDAI
4783:MBDB
4778:HPTP
4709:3-CA
4562:MPTP
4537:HPTP
4208:5-MT
4193:5-CT
4157:pFPP
4152:pCPP
4147:oMPP
4127:mCPP
4122:MBZP
4117:DCPP
4081:PMMA
4076:PMEA
4036:MMMA
4026:MMDA
3996:MDOH
3976:MDEA
3966:MBDB
3916:EDMA
3911:EBDB
3906:DMMA
3806:4-HA
3796:4-FA
3734:MDAT
3703:MMAI
3693:MDAI
3688:ETAI
3683:AMMI
3659:SRAs
3559:4-BP
3554:2-BP
3549:2-AT
3544:2-AI
3523:pFPP
3518:oMPP
3503:mCPP
3498:MBZP
3303:MDOH
3283:MDEA
3273:MBDB
3187:EBDB
3182:DMMA
3070:4-MA
3060:4-FA
2934:NRAs
2817:4-BP
2812:2-AT
2807:2-AI
2786:oMPP
2771:MBZP
2646:MDOH
2631:MDEA
2621:MBDB
2611:MMDA
2499:EBDB
2479:DMMA
2369:4-MA
2359:4-FA
2233:DRAs
2028:MDAT
2006:MEAI
2001:MMAI
1991:MDAI
1986:ETAI
1981:BFAI
1976:AMMI
1921:5-IT
1829:MDPH
1824:MDMP
1817:MBDB
1812:EBDB
1785:MMDA
1780:MDOH
1765:MDEA
1755:EIDA
1700:EDMA
1693:mMMA
1688:PMMA
1683:PMEA
1638:4-MA
1633:4-FA
1522:2015
1488:PMID
1444:PMID
1401:PMID
1358:PMID
1323:PMID
1288:PMID
1253:PMID
1217:PMID
1173:PMID
1120:PMID
1076:PMID
1041:PMID
1003:PMID
987:PMID
952:PMID
925:PMID
882:PMID
847:PMID
811:PMID
776:PMID
740:PMID
652:MEAI
581:MBDB
575:and
564:MDMA
544:MDMA
497:Pd/C
457:The
418:drug
410:MDAI
242:UNII
122:NpSG
81:none
68:Oral
32:MDAI
4838:PIA
4828:PCA
4823:PBA
4773:HPP
4744:DCA
4739:αET
4532:HPP
4223:DMT
4218:αMT
4213:αET
4112:BZP
4086:TAP
4071:PMA
4066:pIA
4061:pCA
4056:pBA
4041:NAP
4021:MMA
3946:IAP
3901:DMA
3886:DCA
3851:BOH
3846:BDB
3708:TAI
3493:BZP
3177:DMA
3137:BOH
3127:BDB
2766:BZP
2474:DMA
2429:BOH
2424:BDB
2139:αMT
2134:αET
2016:TAI
1807:BDB
1678:PMA
1673:MMA
1480:doi
1436:doi
1432:341
1428:BMJ
1393:doi
1350:doi
1315:doi
1245:doi
1209:doi
1165:doi
1112:doi
1068:doi
1033:doi
1019:258
979:doi
948:255
917:doi
874:doi
839:doi
803:doi
799:200
768:doi
732:doi
577:DOM
573:LSD
493:DOM
463:MDA
424:at
267:EPA
201:CID
4925::
4906:•
4902:•
4898:•
4894:•
4890:•
4886:•
4882:•
4469:,
4439:5-
4360:•
4356:•
4352:•
4348:•
4344:•
4340:•
4282:;
3424:IA
3386:CA
3378:BA
2690:IA
2682:CA
2674:BA
1555:.
1494:.
1486:.
1476:28
1474:.
1450:.
1442:.
1430:.
1407:.
1399:.
1389:27
1387:.
1364:.
1356:.
1346:59
1344:.
1321:.
1311:52
1309:.
1282:.
1259:.
1251:.
1241:40
1239:.
1215:.
1205:34
1203:.
1179:.
1171:.
1163:.
1151:38
1149:.
1126:.
1118:.
1108:69
1106:.
1082:.
1074:.
1064:31
1062:.
1039:.
1031:.
1017:.
993:.
985:.
975:38
973:.
946:.
923:.
913:18
911:.
888:.
880:.
870:95
868:.
845:.
835:36
833:.
809:.
797:.
774:.
764:17
762:.
738:.
728:33
726:.
714:^
665:NO
663:11
659:10
546:.
526:50
524:IC
514:.
509:SO
313:11
307:10
129:UK
117:DE
104:BR
4766:N
4687:2
4620:2
4568:N
4473:)
4441:S
4422:3
4396:e
4389:t
4382:v
3640:)
3636:(
3453:)
3449:D
3422:p
3384:p
3376:p
2688:p
2680:p
2672:p
2410:)
2401:(
2216:e
2209:t
2202:v
1590:e
1583:t
1576:v
1524:.
1502:.
1482::
1458:.
1438::
1415:.
1395::
1372:.
1352::
1329:.
1317::
1294:.
1284:9
1267:.
1247::
1223:.
1211::
1187:.
1167::
1134:.
1114::
1090:.
1070::
1047:.
1035::
1001:.
981::
958:.
931:.
919::
896:.
876::
853:.
841::
817:.
805::
782:.
770::
746:.
734::
708:.
667:2
661:H
657:C
511:4
507:2
505:H
412:(
345:)
322:2
319:O
316:N
310:H
304:C
269:)
265:(
165:H
131::
106::
20:)
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