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You are currently exploring Phentermine.
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6057
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IUPAC: 2-Methyl-1-phenylpropan-2-amine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: DHHVAGZRUROJKS-UHFFFAOYSA-N InChI=1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3 PubChem CID: 4771; ChemSpider: 4607 Shulgin Index: Table: 2 Page: 319 Row: 7 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction. Trends Pharmacol. Sci., 1 Dec 2006, 27 (12), 612–618. 519 kB. doi:10.1016/j.tips.2006.10.006 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions. AAPS J., 2007, 9 (1), E1–E10. 999 kB. doi:10.1208/aapsj0901001 Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622 |
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One N analogue:
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6056
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Analogue 1: Adding Methyl at N
Mephentermine IUPAC: N,2-Dimethyl-1-phenylpropan-2-amine Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: RXQCGGRTAILOIN-UHFFFAOYSA-N InChI=1S/C11H17N/c1-11(2,12-3)9-10-7-5-4-6-8-10/h4-8,12H,9H2,1-3H3 PubChem CID: 3677; ChemSpider: 3549 Shulgin Index: Table: 2 Page: 319 Row: 6 Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003 |
Six α analogues:
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142
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Analogue 1: Removing Dimethyl at α
PEA IUPAC: 2-Phenylethanamine Formula: C8H11N Molecular weight: 121.17964 g/mol InChI Key: BHHGXPLMPWCGHP-UHFFFAOYSA-N InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 PubChem CID: 1001; ChemSpider: 13856352; Wikipedia: Phenethylamine Shulgin Index: #107 PEA; Table: 2 Page: 318 Row: 1
Repke, DB; Ferguson, WJ; Bates, DK. Synthesis of secondary methylalkylamines. Tetrahedron Lett., 1979, 20 (43), 4183–4184. 149 kB. doi:10.1016/S0040-4039(01)86538-2 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003 Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622 Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127 Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010. |
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2006
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Analogue 2: Substituting Methyl for Dimethyl at α
Amphetamine IUPAC: 1-Phenylpropan-2-amine Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: KWTSXDURSIMDCE-UHFFFAOYSA-N InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 PubChem CID: 3007; ChemSpider: 13852819; Drugs Forum: Amphetamine; Erowid: Amphetamines; Wikipedia: Amphetamine
Thunhorst, M; Holzgrabe, U. Utilizing NMR spectroscopy for assessing drug enantiomeric composition. Magn. Reson. Chem., 1 Mar 1998, 36 (3), 211–216. 237 kB. doi:10.1002/(SICI)1097-458X(199803)363211AID-OMR2463.0.CO;2-Y Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioural effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. doi:10.1007/s00213-002-1141-z Huang, X; Nichols, DE. 5-HT2 receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 1 Jan 1993, 238 (2–3), 291–296. 553 kB. doi:10.1016/0014-2999(93)90859-G Woolverton, WL; Shybut, G; Johanson, CE. Structure-activity relationships among some d-N-alkylated amphetamines. Pharmacol. Biochem. Behav., 1 Jan 1980, 13 (6), 869–876. 783 kB. doi:10.1016/0091-3057(80)90221-X Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. doi:10.1016/0091-3057(94)00348-3 Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 Vilches-Herrera, M; Miranda-Sepúlveda, J; Rebolledo-Fuentes, M; Fierro, A; Lühr, S; Iturriaga-Vasquez, P; Cassels, BK; Reyes-Parada, M. Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors. Bioorg. Med. Chem., 15 Mar 2009, 17 (6), 2452–2460. 509 kB. doi:10.1016/j.bmc.2009.01.074 Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003 Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction. Trends Pharmacol. Sci., 1 Dec 2006, 27 (12), 612–618. 519 kB. doi:10.1016/j.tips.2006.10.006 Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014 Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009 Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017 McGraw, NP; Callery, PS; Castagnoli, N. In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction. J. Med. Chem., 1 Jan 1977, 20 (2), 185–189. 661 kB. doi:10.1021/jm00212a001 Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 Hathaway, BA; Nichols, DE; Nichols, MB; Yim, GKW. A new, potent, conformationally-restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene. J. Med. Chem., 1 Jan 1982, 25 (5), 535–538. 563 kB. doi:10.1021/jm00347a011 Reviriego, F; Navarro, P; Domènech, A; García-España, E. Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure. J. Chem. Soc., Perkin Trans. 2, 2002, 1634–1638. 115 kB. doi:10.1039/b200607c Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta pharmacol. Et toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions. AAPS J., 2007, 9 (1), E1–E10. 999 kB. doi:10.1208/aapsj0901001 Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB. Alles, GA; Feigen, GA. Comparative physiological actions of phenyl-, thienyl- and furylisopropylamines. J. Pharmacol. Exp. Ther., 1 Jul 1941, 72 (3), 265–275. 1459 kB. Nichols, DE. Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: Entactogens. J. Psychoactive Drugs, 1 Jan 1986, 18 (4), 305–313. 10675 kB. Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010. |
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2365
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Analogue 3: Substituting Ethyl for Dimethyl at α
AEPEA IUPAC: 1-Phenylbutan-2-amine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: IOLQWLOHKZENDW-UHFFFAOYSA-N InChI=1S/C10H15N/c1-2-10(11)8-9-6-4-3-5-7-9/h3-7,10H,2,8,11H2,1H3 PubChem CID: 103771; ChemSpider: 93687; Wikipedia: Phenylisobutylamine Shulgin Index: See #107 PEA; Table: 2 Page: 319 Row: 9 Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V |
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460
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Analogue 4: Substituting Methyl for Dimethyl at α
β-FA IUPAC: 1-Fluoro-1-phenylpropan-2-amine Formula: C9H12FN Molecular weight: 153.1966832 g/mol InChI Key: PPZYDZIZQRVGPE-UHFFFAOYSA-N InChI=1S/C9H12FN/c1-7(11)9(10)8-5-3-2-4-6-8/h2-7,9H,11H2,1H3 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 |
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459
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Analogue 5: Substituting 2-Fluoroethyl for Dimethyl at α
α-FA IUPAC: 1-Fluoro-3-phenylpropan-2-amine Formula: C9H12FN Molecular weight: 153.1966832 g/mol InChI Key: DRCPTTFLGZCUKR-UHFFFAOYSA-N InChI=1S/C9H12FN/c10-7-9(11)6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2 PubChem CID: 5064599; ChemSpider: 4241560 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 |
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457
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Analogue 6: Substituting Trifluoromethyl for Dimethyl at α
α-TFMA IUPAC: 1,1,1-Trifluoro-3-phenylpropan-2-amine Formula: C9H10F3N Molecular weight: 189.1776096 g/mol InChI Key: ISYDGOJLGJTVQL-UHFFFAOYSA-N InChI=1S/C9H10F3N/c10-9(11,12)8(13)6-7-4-2-1-3-5-7/h1-5,8H,6,13H2 PubChem CID: 3820972; ChemSpider: 3047432 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 |
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One β analogue:
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6058
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Analogue 1: Adding Methyl at β
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One R2 analogue:
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6064
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Analogue 1: Adding Chloro at R2
2-Cl-α,α-MePEA IUPAC: 1-(2-Chlorophenyl)-2-methylpropan-2-amine Formula: C10H14ClN Molecular weight: 183.67786 g/mol InChI Key: HXCXASJHZQXCKK-UHFFFAOYSA-N InChI=1S/C10H14ClN/c1-10(2,12)7-8-5-3-4-6-9(8)11/h3-6H,7,12H2,1-2H3 PubChem CID: 25223; ChemSpider: 23558 Shulgin Index: See #74 2-MA; Table: 3 Page: 319 Row: 14 |
Two R4 analogues:
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6219
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Analogue 1: Adding Chloro at R4
4-Cl-α,α-MePEA IUPAC: 1-(4-Chlorophenyl)-2-methylpropan-2-amine Formula: C10H14ClN Molecular weight: 183.67786 g/mol InChI Key: ZCKAMNXUHHNZLN-UHFFFAOYSA-N InChI=1S/C10H14ClN/c1-10(2,12)7-8-3-5-9(11)6-4-8/h3-6H,7,12H2,1-2H3 PubChem CID: 10007; ChemSpider: 9613 Shulgin Index: See #106 PCA; Table: 3 Page: 322 Row: 19 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction. Trends Pharmacol. Sci., 1 Dec 2006, 27 (12), 612–618. 519 kB. doi:10.1016/j.tips.2006.10.006 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions. AAPS J., 2007, 9 (1), E1–E10. 999 kB. doi:10.1208/aapsj0901001 Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta pharmacol. Et toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x |
6317
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Analogue 2: Adding Methoxy at R4
α,α-Me-PMPEA IUPAC: 1-(4-Methoxyphenyl)-2-methylpropan-2-amine Formula: C11H17NO Molecular weight: 179.25878 g/mol InChI Key: DUMKDWRRTLFHTA-UHFFFAOYSA-N InChI=1S/C11H17NO/c1-11(2,12)8-9-4-6-10(13-3)7-5-9/h4-7H,8,12H2,1-3H3 PubChem CID: 91892; ChemSpider: 82975 Shulgin Index: See #110 PMA; Table: 3 Page: 324 Row: 17 Nichols, DE; Lloyd, DH; Hoffman, AJ; Nichols, MB; Yim, GKW. Effects of certain hallucinogenic amphetamine analogues on the release of [3H]-serotonin from rat brain synaptosomes. J. Med. Chem., 1 Jan 1982, 25 (5), 530–535. 804 kB. doi:10.1021/jm00347a010 |
36 skeleton analogues:
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2004
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Analogue 1: With 2-Amino-1-phenylethanone skeleton
Cathinone IUPAC: 2-Amino-1-phenylpropan-1-one Formula: C9H11NO Molecular weight: 149.18974 g/mol InChI Key: PUAQLLVFLMYYJJ-UHFFFAOYSA-N InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3 PubChem CID: 107786; ChemSpider: 96940; Erowid: Cathinone & Methcathinone; Wikipedia: Cathinone Shulgin Index: Table: 2 Page: 318 Row: 29
Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. doi:10.1016/0091-3057(94)00348-3 Dal Cason, TA; Young, R; Glennon, RA. Cathinone: An investigation of several N-alkyl and methylenedioxy-substituted analogs. Pharmacol. Biochem. Behav., 1 Jan 1997, 58 (4), 1109–1116. 97 kB. doi:10.1016/S0091-3057(97)00323-7 Archer, RP. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1355 kB. doi:10.1016/j.forsciint.2008.11.013 Gambaro, V; Arnoldi, S; Colombo, ML; Dell’Acqua, L; Guerrini, K; Roda, G. Determination of the active principles of Catha Edulis: Quali-quantitative analysis of cathinone, cathine, and phenylpropanolamine. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 87–92. 479 kB. doi:10.1016/j.forsciint.2011.09.028 Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009 Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. doi:10.1124/jpet.103.053975 Iversen, L. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. Toole, KE; Fu, S; Shimmon, RG; Kraymen, M; Taflaga, S. Color tests for the preliminary identification of methcathinone and analogues of methcathinone. Microgram J., 2012, 9 (1), 27–32. 496 kB. Shulgin, AT. Cathinone. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 Jun 2004. |
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2114
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Analogue 2: With 2-Cyclic-amine-1-phenylethanone skeleton
α-PPP IUPAC: 1-Phenyl-2-(pyrrolidin-1-yl)propan-1-one Formula: C13H17NO Molecular weight: 203.28018 g/mol InChI Key: KPUJAQRFIJAORQ-UHFFFAOYSA-N InChI=1S/C13H17NO/c1-11(14-9-5-6-10-14)13(15)12-7-3-2-4-8-12/h2-4,7-8,11H,5-6,9-10H2,1H3 PubChem CID: 209045; ChemSpider: 181124; Wikipedia: Alpha-Pyrrolidinopropiophenone Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 30 Maurer, HH; Kraemer, T; Springer, D; Staack, RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (Ecstasy), piperazine, and pyrrolidinophenone types. A synopsis. Ther. Drug Monit., 1 Apr 2004, 26 (2), 127–131. 121 kB. Iversen, L. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. doi:10.2174/1389200054021825 |
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2357
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Analogue 3: With 2,3-Dihydro-1H-inden-2-amine skeleton
2-AI IUPAC: 2,3-Dihydro-1H-inden-2-amine Formula: C9H11N Molecular weight: 133.19034 g/mol InChI Key: LMHHFZAXSANGGM-UHFFFAOYSA-N InChI=1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2 PubChem CID: 76310; ChemSpider: 68787; Erowid: 2-Aminoindan; Wikipedia: 2-Aminoindane Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009 |
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400
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Analogue 4: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton
2-AT IUPAC: 1,2,3,4-Tetrahydronaphthalen-2-amine Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: LCGFVWKNXLRFIF-UHFFFAOYSA-N InChI=1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 PubChem CID: 34677; ChemSpider: 31912; Wikipedia: 2-Aminotetralin Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009 Barfknecht, CF; Nichols, DE; Rusterholz, DB; Long, JP; Engelbrecht, JA; Beaton, JM; Bradley, RJ; Dyer, DC. Potential psychotomimetics. 2-Amino-1,2,3,4-tetrahydronaphthalene analogs. J. Med. Chem., 1 Jan 1973, 16, (7), 804–808. 614 kB. doi:10.1021/jm00265a013 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 |
|||||
801
|
Analogue 5: With 1-Phenylpiperazine skeleton
PP IUPAC: 1-Phenylpiperazine Formula: C10H14N2 Molecular weight: 162.23156 g/mol InChI Key: YZTJYBJCZXZGCT-UHFFFAOYSA-N InChI=1S/C10H14N2/c1-2-4-10(5-3-1)12-8-6-11-7-9-12/h1-5,11H,6-9H2 PubChem CID: 7096; ChemSpider: 6829; Wikipedia: Phenylpiperazine Shulgin Index: See #24 oCPP; Table: 8 Page: 357 Row: 1 Schoenwald, RD; Gadiraju, RR; Barfknecht, CF. Serotonin antagonists for use as antiglaucoma agents and their ocular penetration. Eur. J. Pharm. Biopharm., 1 Jun 1997, 43 (3), 273–281. 688 kB. doi:10.1016/S0939-6411(97)00055-6 |
|||||
903
|
Analogue 6: With 1-Benzylpiperazine skeleton
BZP IUPAC: 1-Benzylpiperazine Formula: C11H16N2 Molecular weight: 176.25814 g/mol InChI Key: IQXXEPZFOOTTBA-UHFFFAOYSA-N InChI=1S/C11H16N2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h1-5,12H,6-10H2 PubChem CID: 75994; ChemSpider: 68493; Wikipedia: Benzylpiperazine Shulgin Index: Table: 9 Page: 357 Row: 19 Schep, LJ; Slaughter, RJ; Temple, WA; Gee, P. Comments on BZP and New Zealand’s alternative approach to prohibition. Drug Test. Anal., 1 Jan 2012, 4 (1), 57. 47 kB. doi:10.1002/dta.356 Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3),. 1364 kB. doi:10.1016/j.forsciint.2011.08.005 Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003 Baumann, MH; Clark, RD; Budzynski, AG; Partilla, JS; Blough, BE; Rothman, RB. N-Substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or ‘Ecstasy’). Neuropsychopharmacology, 1 Mar 2005, 30 (3), 550–560. 184 kB. doi:10.1038/sj.npp.1300585 Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622 Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. doi:10.2174/1389200054021825 Anon. Report on the risk assessment of BZP in the framework of the Council decision on new psychoactive substances, European Monitoring Centre for Drugs and Drug Addiction, 2009. doi:10.2810/44197 |
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902
|
Analogue 7: With Phenylmethanamine skeleton
α-Me-benzylamine IUPAC: 1-Phenylethanamine Formula: C8H11N Molecular weight: 121.17964 g/mol InChI Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 PubChem CID: 7408; ChemSpider: 7130; Wikipedia: 1-Phenylethylamine Shulgin Index: See #107 PEA; Table: 9 Page: 357 Row: 18 King, LA; Meer, AJP; Huizer, H. 1-Phenylethylamines: a new series of illicit drugs?. Forensic Sci. Int., 9 Feb 1996, 77 (3), 141–149. 491 kB. doi:10.1016/0379-0738(95)01852-2 |
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901
|
Analogue 8: With Phenylmethanamine skeleton
Benzylamine IUPAC: 1-Phenylmethanamine Formula: C7H9N Molecular weight: 107.15306 g/mol InChI Key: WGQKYBSKWIADBV-UHFFFAOYSA-N InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2 PubChem CID: 7504; ChemSpider: 7223; Wikipedia: Benzylamine Shulgin Index: See #107 PEA; Table: 9 Page: 357 Row: 17 |
|||||
601
|
Analogue 9: With 3-Phenylpropan-1-amine skeleton
homo-PEA IUPAC: 3-Phenylpropan-1-amine Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: LYUQWQRTDLVQGA-UHFFFAOYSA-N InChI=1S/C9H13N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8,10H2 PubChem CID: 16259; ChemSpider: 15427 Shulgin Index: See #107 PEA; Table: 10 Page: 358 Row: 8 Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017 |
|||||
6007
|
Analogue 10: With Phenylethyl-cyclic-amine skeleton
pip-PEA IUPAC: 1-(2-Phenylethyl)piperidine Formula: C13H19N Molecular weight: 189.29666 g/mol InChI Key: DBDVAKGHPZJLTH-UHFFFAOYSA-N InChI=1S/C13H19N/c1-3-7-13(8-4-1)9-12-14-10-5-2-6-11-14/h1,3-4,7-8H,2,5-6,9-12H2 PubChem CID: 9513; ChemSpider: 9141 Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 7 |
|||||
6012
|
Analogue 11: With 2-Amino-1-phenylethanone skeleton
AA IUPAC: 2-Amino-1-phenylethanone Formula: C8H9NO Molecular weight: 135.16316 g/mol InChI Key: HEQOJEGTZCTHCF-UHFFFAOYSA-N InChI=1S/C8H9NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6,9H2 PubChem CID: 11952; ChemSpider: 11458 Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 12 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 |
|||||
6028
|
Analogue 12: With Phenyl-cyclic-amine skeleton
Phenmetrazine IUPAC: 3-Methyl-2-phenylmorpholine Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: OOBHFESNSZDWIU-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3 PubChem CID: 4762; ChemSpider: 4598 Shulgin Index: Table: 2 Page: 318 Row: 28 Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622 |
|||||
6031
|
Analogue 13: With 2-Cyclic-amine-1-phenylethanone skeleton
PIAP IUPAC: 1-Phenyl-2-(piperidin-1-yl)propan-1-one Formula: C14H19NO Molecular weight: 217.30676 g/mol InChI Key: GEHIWZFQDZBTBY-UHFFFAOYSA-N InChI=1S/C14H19NO/c1-12(15-10-6-3-7-11-15)14(16)13-8-4-2-5-9-13/h2,4-5,8-9,12H,3,6-7,10-11H2,1H3 PubChem CID: 458526; ChemSpider: 403511 Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 31 |
|||||
6032
|
Analogue 14: With 2-Cyclic-amine-1-phenylethanone skeleton
PZAP IUPAC: 2-(4-Methylpiperazin-1-yl)-1-phenylpropan-1-one Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: VJYLTZJATFKDGJ-UHFFFAOYSA-N InChI=1S/C14H20N2O/c1-12(16-10-8-15(2)9-11-16)14(17)13-6-4-3-5-7-13/h3-7,12H,8-11H2,1-2H3 PubChem CID: 43227278 Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 32 |
|||||
6055
|
Analogue 15: With 2-Phenylcyclopropan-1-amine skeleton
cPr-PEA IUPAC: 2-Phenylcyclopropanamine Formula: C9H11N Molecular weight: 133.19034 g/mol InChI Key: AELCINSCMGFISI-UHFFFAOYSA-N InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2 PubChem CID: 5530; ChemSpider: 5329 Shulgin Index: See #107 PEA; Table: 2 Page: 319 Row: 5 Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014 Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 |
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2462
|
Analogue 16: With 2-Amino-3,4-dihydronaphthalen-1(2H)-one skeleton
bk-2-AT IUPAC: 2-Amino-3,4-dihydronaphthalen-1(2H)-one Formula: C10H11NO Molecular weight: 161.20044 g/mol InChI Key: MUGWUYGVUZLWRB-UHFFFAOYSA-N InChI=1S/C10H11NO/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-4,9H,5-6,11H2 PubChem CID: 412890; ChemSpider: 365595 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 |
|||||
2463
|
Analogue 17: With 1-(3,4-Dihydronaphthalen-1-yl)methanamine skeleton
IUPAC: 1-(3,4-Dihydronaphthalen-1-yl)methanamine Formula: C11H13N Molecular weight: 159.22762 g/mol InChI Key: WNFNQSTXHLQIED-UHFFFAOYSA-N InChI=1S/C11H13N/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-2,4,6-7H,3,5,8,12H2 PubChem CID: 12914860; ChemSpider: 14442059 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 |
|||||
2465
|
Analogue 18: With 1-(2H-Chromen-4-yl)methanamine skeleton
IUPAC: 1-(2H-Chromen-4-yl)methanamine Formula: C10H11NO Molecular weight: 161.20044 g/mol InChI Key: WRQGQTBQEWMFLP-UHFFFAOYSA-N InChI=1S/C10H11NO/c11-7-8-5-6-12-10-4-2-1-3-9(8)10/h1-5H,6-7,11H2 PubChem CID: 12914869 Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012 |
|||||
544
|
Analogue 19: With 1,2-Dihydronaphthalen-2-amine skeleton
2-ADN IUPAC: 1,2-Dihydronaphthalen-2-amine Formula: C10H11N Molecular weight: 145.20104 g/mol InChI Key: SHLZSYAMFQNEOF-UHFFFAOYSA-N InChI=1S/C10H11N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-6,10H,7,11H2 PubChem CID: 133605; ChemSpider: 117856; Wikipedia: 2-Amino-1,2-dihydronaphthalene Hathaway, BA; Nichols, DE; Nichols, MB; Yim, GKW. A new, potent, conformationally-restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene. J. Med. Chem., 1 Jan 1982, 25 (5), 535–538. 563 kB. doi:10.1021/jm00347a011 Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V |
|||||
561
|
Analogue 20: With Phenyl-cyclic-amine skeleton
|
|||||
562
|
Analogue 21: With Phenyl-cyclic-amine skeleton
4-MAR IUPAC: 4-Methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine Formula: C10H12N2O Molecular weight: 176.21508 g/mol InChI Key: LJQBMYDFWFGESC-UHFFFAOYSA-N InChI=1S/C10H12N2O/c1-7-9(13-10(11)12-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H2,11,12) PubChem CID: 92196; ChemSpider: 83237; Wikipedia: 4-Methylaminorex |
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1235
|
Analogue 22: With Phenyl-cyclic-amine skeleton
|
|||||
542
|
Analogue 23: With Phenylacetaldehyde skeleton
P2P IUPAC: 1-Phenylpropan-2-one Formula: C9H10O Molecular weight: 134.1751 g/mol InChI Key: QCCDLTOVEPVEJK-UHFFFAOYSA-N InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3 PubChem CID: 7678; ChemSpider: 21106366 Barfknecht, CF; Smith, RV; Nichols, DE; Leseney, JL; Long, JP; Engelbrecht, JA. Chemistry and pharmacological evaluation of 1-phenyl-2-propanols and 1-phenyl-2-propanones. J. Pharm. Sci., 1 May 1971, 60 (5), 799–801. 352 kB. doi:10.1002/jps.2600600533 |
|||||
1141
|
Analogue 24: With Prop-2-en-1-ylbenzene skeleton
IUPAC: Prop-2-en-1-ylbenzene Formula: C9H10 Molecular weight: 118.1757 g/mol InChI Key: HJWLCRVIBGQPNF-UHFFFAOYSA-N InChI=1S/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-5,7-8H,1,6H2 PubChem CID: 9309; ChemSpider: 8950 Nichols, DE; Mason, DL; Jacobsen, LB. Allylbenzene analogs of Δ9-tetrahydrocannabinol as tumor growth inhibitors. Life Sci., 1 Nov 1977, 21 (9), 1245–1247. 150 kB. doi:10.1016/0024-3205(77)90004-2 |
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![6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine](C/pk1307.png "Explore the structure and analogues of 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine")
1307
|
Analogue 25: With 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine skeleton
IUPAC: 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: MDVRGZASGHPBAG-UHFFFAOYSA-N InChI=1S/C11H15N/c12-11-7-3-6-9-4-1-2-5-10(9)8-11/h1-2,4-5,11H,3,6-8,12H2 PubChem CID: 41896; ChemSpider: 38228 Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009 |
|||||
1511
|
Analogue 26: With 1-Benzylcyclopropan-1-amine skeleton
|
|||||
1502
|
Analogue 27: With 2-Phenylcyclopropan-1-amine skeleton
IUPAC: 2,3-Diphenylcyclopropanamine Formula: C15H15N Molecular weight: 209.2863 g/mol InChI Key: RYTXAPKVNHVKAX-UHFFFAOYSA-N InChI=1S/C15H15N/c16-15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10,13-15H,16H2 PubChem CID: 12523667 Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018 |
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1500
|
Analogue 28: With 2-Phenylcyclopropan-1-amine skeleton
IUPAC: 2-Methyl-3-phenylcyclopropanamine Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: VYDUHLWMQFOCQJ-UHFFFAOYSA-N InChI=1S/C10H13N/c1-7-9(10(7)11)8-5-3-2-4-6-8/h2-7,9-10H,11H2,1H3 PubChem CID: 55289096 Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018 |
|||||
1499
|
Analogue 29: With 2-Phenylcyclopropan-1-amine skeleton
IUPAC: 2,2-Diphenylcyclopropanamine Formula: C15H15N Molecular weight: 209.2863 g/mol InChI Key: WVRNJJILWVMIRA-UHFFFAOYSA-N InChI=1S/C15H15N/c16-14-11-15(14,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11,16H2 PubChem CID: 12345941; ChemSpider: 13566302 Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018 |
|||||
1498
|
Analogue 30: With 2-Phenylcyclopropan-1-amine skeleton
IUPAC: 1-Methyl-2-phenylcyclopropanamine Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: MHQDTOHVMGQLTE-UHFFFAOYSA-N InChI=1S/C10H13N/c1-10(11)7-9(10)8-5-3-2-4-6-8/h2-6,9H,7,11H2,1H3 PubChem CID: 54072774 Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018 |
|||||
1497
|
Analogue 31: With 2-Phenylcyclopropan-1-amine skeleton
IUPAC: 2-Methyl-2-phenylcyclopropanamine Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: DZOORLACDVEKJC-UHFFFAOYSA-N InChI=1S/C10H13N/c1-10(7-9(10)11)8-5-3-2-4-6-8/h2-6,9H,7,11H2,1H3 PubChem CID: 54595265; ChemSpider: 27909807 Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018 |
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1471
|
Analogue 32: With 2-Phenylcyclobutan-1-amine skeleton
IUPAC: 2-Phenylcyclobutanamine Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: PKMQLQANCCIABY-UHFFFAOYSA-N InChI=1S/C10H13N/c11-10-7-6-9(10)8-4-2-1-3-5-8/h1-5,9-10H,6-7,11H2 PubChem CID: 19703781 Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018 |
|||||
1438
|
Analogue 33: With Phenyl-cyclic-amine skeleton
Thozalinone IUPAC: 2-(Dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one Formula: C11H12N2O2 Molecular weight: 204.22518 g/mol InChI Key: JJSHYECKYLDYAR-UHFFFAOYSA-N InChI=1S/C11H12N2O2/c1-13(2)11-12-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3 PubChem CID: 12602; ChemSpider: 12082; Wikipedia: Thozalinone |
|||||
1437
|
Analogue 34: With Phenyl-cyclic-amine skeleton
|
|||||
1435
|
Analogue 35: With Phenyl-cyclic-amine skeleton
Fenozolone IUPAC: 2-(Ethylamino)-5-phenyl-1,3-oxazol-4(5H)-one Formula: C11H12N2O2 Molecular weight: 204.22518 g/mol InChI Key: RXOIEVSUURELPG-UHFFFAOYSA-N InChI=1S/C11H12N2O2/c1-2-12-11-13-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,13,14) PubChem CID: 71682; ChemSpider: 64736; Wikipedia: Fenozolone |
|||||
1434
|
Analogue 36: With Phenyl-cyclic-amine skeleton
Cyclazodone IUPAC: 2-(Cyclopropylamino)-5-phenyl-1,3-oxazol-4(5H)-one Formula: C12H12N2O2 Molecular weight: 216.23588 g/mol InChI Key: DNRKTAYPGADPGW-UHFFFAOYSA-N InChI=1S/C12H12N2O2/c15-11-10(8-4-2-1-3-5-8)16-12(14-11)13-9-6-7-9/h1-5,9-10H,6-7H2,(H,13,14,15) PubChem CID: 26701; ChemSpider: 24875; Wikipedia: Cyclazodone |
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15 isomers:
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219
|
Isomer 1
2-MeA IUPAC: 1-(2-Methylphenyl)propan-2-amine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: ZEMQBDFHXOOXLY-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-5-3-4-6-10(8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 PubChem CID: 115808; ChemSpider: 103572; Wikipedia: Ortetamine Shulgin Index: See #111 PMeA; Table: 3 Page: 319 Row: 20
Higgs, RA; Glennon, RA. Stimulus properties of ring-methyl amphetamine analogs. Pharmacol. Biochem. Behav., 1 Dec 1990, 37 (4), 835–837. 238 kB. doi:10.1016/0091-3057(90)90571-X Davis, S; Blakey, K; Rands-Trevor, K. GC-MS and GC-IRD analysis of 2-, 3- and 4-methylmethamphetamine and 2-, 3- and 4-methylamphetamine. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 67–73. 1158 kB. doi:10.1016/j.forsciint.2012.01.028 |
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220
|
Isomer 2
3-MeA IUPAC: 1-(3-Methylphenyl)propan-2-amine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: KCTJOEASAHXBBW-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-4-3-5-10(6-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 PubChem CID: 115806; ChemSpider: 103570; Wikipedia: 3-Methylamphetamine Shulgin Index: See #111 PMeA; Table: 3 Page: 321 Row: 1
Higgs, RA; Glennon, RA. Stimulus properties of ring-methyl amphetamine analogs. Pharmacol. Biochem. Behav., 1 Dec 1990, 37 (4), 835–837. 238 kB. doi:10.1016/0091-3057(90)90571-X Davis, S; Blakey, K; Rands-Trevor, K. GC-MS and GC-IRD analysis of 2-, 3- and 4-methylmethamphetamine and 2-, 3- and 4-methylamphetamine. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 67–73. 1158 kB. doi:10.1016/j.forsciint.2012.01.028 Baumann, MH; Clark, RD; Woolverton, WL; Wee, S; Blough, BE; Rothman, RB. In vivo effects of amphetamine analogs reveal evidence for serotonergic inhibition of mesolimbic dopamine transmission in the rat. J. Pharmacol. Exp. Ther., 1 Apr 2011, 337 (1), 218–225. 380 kB. doi:10.1124/jpet.110.176271 |
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221
|
Isomer 3
4-MA IUPAC: 1-(4-Methylphenyl)propan-2-amine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: ZDHZDWSHLNBTEB-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 PubChem CID: 199116; ChemSpider: 172349; Wikipedia: 4-Methylamphetamine Shulgin Index: #111 PMeA; Table: 3 Page: 322 Row: 37
Higgs, RA; Glennon, RA. Stimulus properties of ring-methyl amphetamine analogs. Pharmacol. Biochem. Behav., 1 Dec 1990, 37 (4), 835–837. 238 kB. doi:10.1016/0091-3057(90)90571-X Davis, S; Blakey, K; Rands-Trevor, K. GC-MS and GC-IRD analysis of 2-, 3- and 4-methylmethamphetamine and 2-, 3- and 4-methylamphetamine. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 67–73. 1158 kB. doi:10.1016/j.forsciint.2012.01.028 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction. Trends Pharmacol. Sci., 1 Dec 2006, 27 (12), 612–618. 519 kB. doi:10.1016/j.tips.2006.10.006 Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014 Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016 Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta pharmacol. Et toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x Baumann, MH; Clark, RD; Woolverton, WL; Wee, S; Blough, BE; Rothman, RB. In vivo effects of amphetamine analogs reveal evidence for serotonergic inhibition of mesolimbic dopamine transmission in the rat. J. Pharmacol. Exp. Ther., 1 Apr 2011, 337 (1), 218–225. 380 kB. doi:10.1124/jpet.110.176271 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions. AAPS J., 2007, 9 (1), E1–E10. 999 kB. doi:10.1208/aapsj0901001 Anon. Report on a new psychoactive substance: 4-methylamphetamine, European Monitoring Centre for Drugs and Drug Addiction, 2012. doi:10.2810/73968 |
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2002
|
Isomer 4
MA IUPAC: N-Methyl-1-phenylpropan-2-amine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: MYWUZJCMWCOHBA-UHFFFAOYSA-N InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3 PubChem CID: 1206; ChemSpider: 1169; Drugs Forum: Methamphetamine; Erowid: Methamphetamines; Wikipedia: Methamphetamine Shulgin Index: Table: 2 Page: 318 Row: 16
Baumgarten, HG; Lachenmayer, L. Serotonin neurotoxins—past and present. Neurotox. Res., 1 Jan 2004, 6 (7–8), 589–614. 402 kB. doi:10.1007/BF03033455 Woolverton, WL; Shybut, G; Johanson, CE. Structure-activity relationships among some d-N-alkylated amphetamines. Pharmacol. Biochem. Behav., 1 Jan 1980, 13 (6), 869–876. 783 kB. doi:10.1016/0091-3057(80)90221-X McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. doi:10.1016/0091-3057(91)90005-M Cozzi, NV; Sievert, MK; Shulgin, AT; Jacob, P; Ruoho, AE. Inhibition of plasma membrane monoamine transporters by β-ketoamphetamines. Eur. J. Pharmacol., 1 Jan 1999, 381 (1), 63–69. 111 kB. doi:10.1016/S0014-2999(99)00538-5 Repke, DB; Ferguson, WJ; Bates, DK. Synthesis of secondary methylalkylamines. Tetrahedron Lett., 1979, 20 (43), 4183–4184. 149 kB. doi:10.1016/S0040-4039(01)86538-2 Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003 Baumann, MH; Ayestas, MA; Partilla, JS; Sink, JR; Shulgin, AT; Daley, PF; Brandt, SD; Rothman, RB; Ruoho, AE; Cozzi, NV. The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology, 1 Apr 2012, 37, 1192–1203. 763 kB. doi:10.1038/npp.2011.304 Reviriego, F; Navarro, P; Domènech, A; García-España, E. Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure. J. Chem. Soc., Perkin Trans. 2, 2002, 1634–1638. 115 kB. doi:10.1039/b200607c Buffum, JC; Shulgin, AT. Overdose of 2.3 grams of intravenous methamphetamine: Case, analysis and patient perspective. J. Psychoactive Drugs, 1 Oct 2001, 33 (4), 409–412. 681 kB. doi:10.1080/02791072.2001.10399926 Angoa-Pérez, M; Kane, MJ; Francescutti, DM; Sykes, KE; Shah, MM; Mohammed, AM; Thomas, DM; Kuhn, DM. Mephedrone, an abused psychoactive component of ‘bath salts’ and methamphetamine congener, does not cause neurotoxicity to dopamine nerve endings of the striatum. J. Neurochem., 1 Mar 2012, 120 (6), 1097–1107. 777 kB. doi:10.1111/j.1471-4159.2011.07632.x Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622 Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions. AAPS J., 2007, 9 (1), E1–E10. 999 kB. doi:10.1208/aapsj0901001 Buffum, JC; Shulgin, AT. Overdose of 2.3 grams of intravenous methamphetamine: Case, analysis and patient perspective. J. Psychoactive Drugs, 1 Jan 2001, 33 (4), 409–412. 284 kB. Shulgin, AT. MDMA (Ecstasy) v. Methamphetamine. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 15 Feb 2001. Shulgin, AT. Yaba (methamphetamine). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 9 Mar 2004. Shulgin, AT. Ice, crank, speed or methamphetamine. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 6 Apr 2005. |
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|
2365
|
Isomer 5
AEPEA IUPAC: 1-Phenylbutan-2-amine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: IOLQWLOHKZENDW-UHFFFAOYSA-N InChI=1S/C10H15N/c1-2-10(11)8-9-6-4-3-5-7-9/h3-7,10H,2,8,11H2,1H3 PubChem CID: 103771; ChemSpider: 93687; Wikipedia: Phenylisobutylamine Shulgin Index: See #107 PEA; Table: 2 Page: 319 Row: 9 Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V |
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5556
|
Isomer 6
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6003
|
Isomer 7
N,N-MePEA IUPAC: N,N-Dimethyl-2-phenylethanamine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: TXOFSCODFRHERQ-UHFFFAOYSA-N InChI=1S/C10H15N/c1-11(2)9-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3 PubChem CID: 25125; ChemSpider: 23470 Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 3 Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 |
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6004
|
Isomer 8
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6008
|
Isomer 9
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6255
|
Isomer 10
4-EtPEA IUPAC: 2-(4-Ethylphenyl)ethanamine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: XLJAVPNHXCHBPU-UHFFFAOYSA-N InChI=1S/C10H15N/c1-2-9-3-5-10(6-4-9)7-8-11/h3-6H,2,7-8,11H2,1H3 PubChem CID: 144047; ChemSpider: 127068 Shulgin Index: See #102 4-MPEA; Table: 3 Page: 323 Row: 5 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 |
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6361
|
Isomer 11
2,3-DMePEA IUPAC: 2-(2,3-Dimethylphenyl)ethanamine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: IGMRZOPJPZWRFU-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-4-3-5-10(6-7-11)9(8)2/h3-5H,6-7,11H2,1-2H3 PubChem CID: 22379519; ChemSpider: 11375958 Shulgin Index: See #43 DMePEA; Table: 4 Page: 325 Row: 11 |
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6433
|
Isomer 12
2,4-DMePEA IUPAC: 2-(2,4-Dimethylphenyl)ethanamine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: VQGZTRKXOUWMAC-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-3-4-10(5-6-11)9(2)7-8/h3-4,7H,5-6,11H2,1-2H3 PubChem CID: 414339; ChemSpider: 366885 Shulgin Index: See #43 DMePEA; Table: 4 Page: 326 Row: 33 |
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6808
|
Isomer 13
2,5-DMePEA IUPAC: 2-(2,5-Dimethylphenyl)ethanamine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: RNEFNTMBBIKOFO-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-3-4-9(2)10(7-8)5-6-11/h3-4,7H,5-6,11H2,1-2H3 PubChem CID: 211415; ChemSpider: 183273 Shulgin Index: See #43 DMePEA; Table: 4 Page: 334 Row: 8 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 |
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6918
|
Isomer 14
3,5-DMePEA IUPAC: 2-(3,5-Dimethylphenyl)ethanamine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: QXLUHUARYCYCMG-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-5-9(2)7-10(6-8)3-4-11/h5-7H,3-4,11H2,1-2H3 PubChem CID: 414329; ChemSpider: 366875 Shulgin Index: See #43 DMePEA; Table: 4 Page: 336 Row: 18 |
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6953
|
Isomer 15
2,6-DMePEA IUPAC: 2-(2,6-Dimethylphenyl)ethanamine Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: NVXJQKFBPRPHND-UHFFFAOYSA-N InChI=1S/C10H15N/c1-8-4-3-5-9(2)10(8)6-7-11/h3-5H,6-7,11H2,1-2H3 PubChem CID: 23273462; ChemSpider: 10437317 Shulgin Index: See #43 DMePEA; Table: 4 Page: 337 Row: 3 |
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