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Phentermine
6057
Variant: N α β R2 R4 skeleton isomers all
Analogues: 1 5 1 1 2 40 20 70

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

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

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

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Edwards, NR. Qualitative and quantitative analysis of Ionamin 30 capsules (containing a time-release formulation of phentermine). Microgram J., 1 Jan 2006, 4 (1–4), 66–69. 115 kB.

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

One N analogue:
6056
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

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Five α analogues:
142
Analogue 1: Removing Dimethyl at α

PEA
β-PEA
2-PEA
β-Phenethylamine
Phenethylamine

IUPAC: 2-Phenylethan-1-amine

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

See also TiHKAL: #2 DBT
#5 α,O-DMS
#8 α,N-DMT
#11 α-ET
#30 4,5-MDO-DMT
#32 5,6-MDO-MIPT
#37 5-MeO-DIPT
#46 5-MeS-DMT
#53 T
#55 α,N,O-TMS

Suter, CM; Weston, AW. Some fluorinated amines of the pressor type. J. Am. Chem. Soc., 1 Feb 1941, 63 (2), 602–605. 444 kB. doi:10.1021/ja01847a069

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Baker, GB; Coutts, RT; Rao, TS. Neuropharmacological and neurochemical properties of N- (2-cyanoethyl)-2-phenylethylamine, a prodrug of 2-phenylethylamine. Br. J. Pharmacol., 1 Oct 1987, 92 (2), 243–255. 1932 kB. doi:10.1111/j.1476-5381.1987.tb11318.x

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; By, AW. The conformation of β-phenylethylamines in solution. Can. J. Pharm. Sci., 1975, 10 (1), 31–32. 117 kB.

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

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

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

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

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

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

Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010.

2006
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

See also TiHKAL: #5 α,O-DMS
#8 α,N-DMT
#13 Harmaline
#48 α-MT
#55 α,N,O-TMS  
See also Pharmacology notes I: p. 133, Amphetamine

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Lurie, IS; Bozenko, JS; Li, L; Miller, EE; Greenfield, SJ. Chiral separation of methamphetamine and related compounds using capillary electrophoresis with dynamically coated capillaries. Microgram J., 1 Jan 2011, 8 (1), 24–28. 786 kB.

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Bustamante, D; Diaz-Véliz, G; Paeile, C; Zapata-Torres, G; Cassels, BK. Analgesic and behavioral effects of amphetamine enantiomers, p-methoxyamphetamine and N-alkyl-p-methoxyamphetamine derivatives. Pharmacol. Biochem. Behav., 1 Oct 2004, 79 (2), 199–212. 404 kB. doi:10.1016/j.pbb.2004.06.017

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; Legault, D. Analysis of the 13C-NMR spectra of mono- and dimethylamphetamines. Anal. Chim. Acta., 1 Jan 1981, 123, 75–82. 654 kB. doi:10.1016/S0003-2670(01)83160-3

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

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

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

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

Aceto, MD; Rosecrans, JA; Young, R; Glennon, RA. Similarity between (+)-amphetamine and amfonelic acid. Pharmacol. Biochem. Behav., 1 Apr 1984, 20 (4), 635–637. 184 kB. doi:10.1016/0091-3057(84)90316-2

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Suter, CM; Weston, AW. Some fluorinated amines of the pressor type. J. Am. Chem. Soc., 1 Feb 1941, 63 (2), 602–605. 444 kB. doi:10.1021/ja01847a069

Felice, LJD; Glennon, RA; Negus, SS. Synthetic cathinones: Chemical phylogeny, physiology, and neuropharmacology. Life Sci., 27 Feb 2014, 97 (1), 20–26. 697 kB. doi:10.1016/j.lfs.2013.10.029

Stojanovska, N; Fu, S; Tahtouh, M; Kelly, T; Beavis, A; Kirkbride, KP. A review of impurity profiling and synthetic route of manufacture of methylamphetamine, 3,4-methylenedioxymethylamphetamine, amphetamine, dimethylamphetamine and p-methoxyamphetamine. Forensic Sci. Int., 10 Jan 2013, 224 (1–3), 8–26. 813 kB. doi:10.1016/j.forsciint.2012.10.040

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

Heal, DJ; Smith, SL; Gosden, J; Nutt, DJ. Amphetamine, past and present—a pharmacological and clinical perspective. J. Psychopharmacol., 1 Jun 2013, 27 (6), 479–496. 740 kB. doi:10.1177/0269881113482532

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Rasmussen, N. Making the first anti-depressant: Amphetamine in American medicine, 1929-1950. J. Hist. Med. Allied Sci., 1 Jul 2006, 61 (3), 288–323. 175 kB. doi:10.1093/jhmas/jrj039

Worsham, JN. 5-HT3 receptor ligands and their effect on psychomotor stimulants. M. Sc. Thesis, Virginia Commonwealth University, Richmond, VA, USA, 1 May 2008. 956 kB.

Oberlender, R; Nichols, DE. Drug discrimination studies with MDMA and amphetamine. Psychopharmacology, 1 May 1988, 95 (1), 71–26. 674 kB. doi:10.1007/BF00212770

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

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

Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta Pharmacol. Toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x

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.

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

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

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

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

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

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

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

Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010.

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

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

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

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

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; 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

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

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

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.

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

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

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. doi:10.1080/02791072.1986.10472362

2365
Analogue 3: Substituting Ethyl for Dimethyl at α

AEPEA
Phenylisobutylamine
α-Ethylphenethylamine

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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-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

459
Analogue 4: 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

457
Analogue 5: 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

One β analogue:
6058
Analogue 1: Adding Methyl at β

Pentorex

IUPAC: 2-Methyl-3-phenylbutan-2-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: UMWAUEZOGHNSCH-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-9(11(2,3)12)10-7-5-4-6-8-10/h4-9H,12H2,1-3H3

PubChem CID: 22031; ChemSpider: 20703

Shulgin Index: Table: 2 Page: 319 Row: 8

One R2 analogue:
6064
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:
6219
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

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

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

Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta Pharmacol. Toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x

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

6317
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

40 skeleton analogues:
2004
Analogue 1: With 2-Amino-1-phenylethanone skeleton

Cathinone
β-Keto-amphetamine

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

See also TiHKAL: #18 4-HO-DMT      

Young, R; Glennon, RA. Cocaine-stimulus generalization to two new designer drugs: Methcathinone and 4-methylaminorex. Pharmacol. Biochem. Behav., 1 May 1993, 45 (1), 209–214. 224 kB. doi:10.1016/0091-3057(93)90110-F

Dawson, BA; Black, DB; Lavoie, A; LeBelle, MJ. Nuclear magnetic resonance identification of the phenylalkylamine alkaloids of khat using a chiral solvating agent. J. Forensic Sci., 1 Jul 1994, 39 (4), 1026–1038. 453 kB. doi:10.1520/JFS13681J

LeBelle, MJ; Lauriault, G; Lavoie, A. Gas chromatographic-mass spectrometric identification of chiral derivatives of the alkaloids of KHAT. Forensic Sci. Int., 1 Sep 1993, 61 (1), 53–64. 900 kB. doi:10.1016/0379-0738(93)90249-A

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

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

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

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.

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

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

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010.

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

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

Shulgin, AT. Cathinone. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 Jun 2004.

Foley, KF. Aminopropiophenones at the norepinephrine transporter: Structure-activity relationships and behavioral effects of methcathinone analogs. Ph. D. Thesis, Brody School of Medicine, Greenville, NC, USA, 1 May 2002. 8573 kB.

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

2114
Analogue 2: With 2-Cyclic-amine-1-phenylethanone skeleton

α-PPP
PPP
α-Pyrrolidinopropiophenone

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

Reitzel, LA; Dalsgaard, PW; Müller, IB; Cornett, C. Identification of ten new designer drugs by GC-MS, UPLC-QTOF-MS, and NMR as part of a police investigation of a Danish Internet company. Drug Test. Anal., 1 May 2012, 4 (5), 342–354. 538 kB. doi:10.1002/dta.358

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

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010.

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.

Rösner, P; Junge, T; Fritschi, G; Klein, B; Thielert, K; Kozlowski, M. Neue synthetische Drogen: Piperazin-, propicyclidin- und α-aminopropiophenonderivate. Toxichem Krimtech, 1999, 66 (2), 81–90. 1202 kB.

2357
Analogue 3: With 2,3-Dihydro-1H-inden-2-amine skeleton

2-AI
2-Aminoindane

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

400
Analogue 4: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

2-AT
2-Aminotetralin

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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-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

Nichols, DE; Pfister, WR; Yim, GKW; Cosgrove, RJ. A new view of the structural relationship between LSD and mescaline. Brain Res. Bull., 1 May 1977, 2 (3), 169–171. 338 kB. doi:10.1016/0361-9230(77)90034-X

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

Rösner, P; Junge, T; Fritschi, G; Klein, B; Thielert, K; Kozlowski, M. Neue synthetische Drogen: Piperazin-, propicyclidin- und α-aminopropiophenonderivate. Toxichem Krimtech, 1999, 66 (2), 81–90. 1202 kB.

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Maurer, HH. Mass spectra of select benzyl- and phenyl- piperazine designer drugs. Microgram J., 1 Jan 2004, 2 (1–4), 22–26. 326 kB.

Wood, DM; Button, J; Lidder, S; Ramsey, J; Holt, DW; Dargan, PI. Dissociative and sympathomimetic toxicity associated with recreational use of 1-(3-trifluoromethylphenyl)piperazine (TFMPP) and 1-benzylpiperzine (BZP). J. Med. Toxicol., 1 Dec 2008, 4 (4), 254–257. 334 kB. doi:10.1007/BF03161209

Byrska, B; Zuba, D; Stanaszek, R. Determination of piperazine derivatives in “legal highs” Probl. Forensic Sci., 2010, 81, 101–113. 852 kB.

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

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

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

Anon. Report on the risk assessment of BZP, European Monitoring Centre for Drugs and Drug Addiction, Feb 2009.

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

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

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

902
Analogue 7: With Phenylmethanamine skeleton

1-PEA
α-PEA
α-Me-benzylamine

IUPAC: 1-Phenylethan-1-amine

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

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

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Banks, ML; Blough, BE; Fennell, TR; Snyder, RW; Negus, SS. Role of phenmetrazine as an active metabolite of phendimetrazine: Evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend., 1 Jun 2013, 130 (1–3), 158–166. 520 kB. doi:10.1016/j.drugalcdep.2012.10.026

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

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

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

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

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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-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

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

561
Analogue 20: With Phenyl-cyclic-amine skeleton

Aminorex

IUPAC: 5-Phenyl-4,5-dihydro-1,3-oxazol-2-amine

Formula: C9H10N2O Molecular weight: 162.1885 g/mol InChI Key: SYAKTDIEAPMBAL-UHFFFAOYSA-N

InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11)

PubChem CID: 16630; Wikipedia: Aminorex

Young, R; Glennon, RA. Cocaine-stimulus generalization to two new designer drugs: Methcathinone and 4-methylaminorex. Pharmacol. Biochem. Behav., 1 May 1993, 45 (1), 209–214. 224 kB. doi:10.1016/0091-3057(93)90110-F

Woolverton, WL; Massey, BW; Winger, G; Patrick, GA; Harris, LS. Evaluation of the abuse liability of aminorex. Drug Alcohol Depend., 1 Dec 1994, 36 (3), 187–192. 711 kB. doi:10.1016/0376-8716(94)90144-9

562
Analogue 21: With Phenyl-cyclic-amine skeleton

4-MAR
4-Methylaminorex

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

Rodriguez, WR; Allred, RA. Synthesis of trans-4-methylaminorex from norephedrine and potassium cyanate. Microgram J., 1 Jul 2005, 3 (3–4), 154–165. 559 kB.

1235
Analogue 22: With Phenyl-cyclic-amine skeleton

Phendimetrazine

IUPAC: 3,4-Dimethyl-2-phenylmorpholine

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: MFOCDFTXLCYLKU-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3

PubChem CID: 12460; ChemSpider: 11950

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

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Banks, ML; Blough, BE; Fennell, TR; Snyder, RW; Negus, SS. Role of phenmetrazine as an active metabolite of phendimetrazine: Evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend., 1 Jun 2013, 130 (1–3), 158–166. 520 kB. doi:10.1016/j.drugalcdep.2012.10.026

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

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

1434
Analogue 26: 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

1435
Analogue 27: 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

1437
Analogue 28: With Phenyl-cyclic-amine skeleton

Pemoline

IUPAC: 2-Imino-5-phenyl-1,3-oxazolidin-4-one

Formula: C9H8N2O2 Molecular weight: 176.17202 g/mol InChI Key: NRNCYVBFPDDJNE-UHFFFAOYSA-N

InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)

PubChem CID: 4723; ChemSpider: 4561; Wikipedia: Pemoline

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

1438
Analogue 29: 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

1471
Analogue 30: 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

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

1498
Analogue 32: 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

1499
Analogue 33: 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

1500
Analogue 34: 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

1502
Analogue 35: 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

1511
Analogue 36: With 1-Benzylcyclopropan-1-amine skeleton

IUPAC: 1-Benzylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: GEQRCQKFLCJFEC-UHFFFAOYSA-N

InChI=1S/C10H13N/c11-10(6-7-10)8-9-4-2-1-3-5-9/h1-5H,6-8,11H2

PubChem CID: 152923; ChemSpider: 134782

2759
Analogue 37: With Phenylmethanamine skeleton

IUPAC: N′-[4-(Dimethylamino)-2-methoxy-5-nitrobenzyl]-N,N-diethylethane-1,2-diamine

Formula: C16H28N4O3 Molecular weight: 324.41852 g/mol InChI Key: GDOQXLINNITIBE-UHFFFAOYSA-N

InChI=1S/C16H28N4O3/c1-6-19(7-2)9-8-17-12-13-10-15(20(21)22)14(18(3)4)11-16(13)23-5/h10-11,17H,6-9,12H2,1-5H3

Dawson, BA; Black, DB; Cyr, TD; Ethier, J; By, AW; Beckstead, HD; Neville, GA. Structural elucidation of unusual police exhibits. I. Dimethpramide ('Dimetcarb'). Forensic Sci. Int., 28 Feb 1995, 71 (3), 169–179. 1376 kB. doi:10.1016/0379-0738(94)01664-X

1047
Analogue 38: With Phenyl-cyclic-amine skeleton

Levamisole

IUPAC: 6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

Formula: C11H12N2S Molecular weight: 204.29138 g/mol InChI Key: HLFSDGLLUJUHTE-UHFFFAOYSA-N

InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2

PubChem CID: 3913; ChemSpider: 3776

1045
Analogue 39: With 3-Phenylpropan-1-amine skeleton

Homoamphetamine

IUPAC: 4-Phenylbutan-2-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: WECUIGDEWBNQJJ-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6,9H,7-8,11H2,1H3

PubChem CID: 31160; ChemSpider: 28910

King, LA. New phenethylamines in Europe. Drug Test. Anal., 20 Nov 2013. 472 kB. doi:10.1002/dta.1570

1027
Analogue 40: With Phenylethyl-cyclic-amine skeleton

W-15

IUPAC: 4-Chloro-N-[(2E)-1-(2-phenylethyl)piperidin-2-ylidene]benzenesulfonamide

Formula: C19H21ClN2O2S Molecular weight: 376.90024 g/mol InChI Key: VJHXSSVOCOBVMI-XUTLUUPISA-N

InChI=1S/C19H21ClN2O2S/c20-17-9-11-18(12-10-17)25(23,24)21-19-8-4-5-14-22(19)15-13-16-6-2-1-3-7-16/h1-3,6-7,9-12H,4-5,8,13-15H2/b21-19+

ChemSpider: 10544257

20 isomers:
219
Isomer 1

2-MeA
2-Methylamphetamine

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

See also PiHKAL: #54 2,5-DMA      

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

Bailey, K; Legault, D. Analysis of the 13C-NMR spectra of mono- and dimethylamphetamines. Anal. Chim. Acta., 1 Jan 1981, 123, 75–82. 654 kB. doi:10.1016/S0003-2670(01)83160-3

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 2618 kB.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Power, JD; Clarke, K; McDermott, SD; McGlynn, P; Barry, M; White, C; O’Brien, J; Kavanagh, P. The identification of 4-methylamphetamine and its synthesis by-products in forensic samples. Forensic Sci. Int., 10 May 2013, 228 (1–3), 115–131. 1893 kB. doi:10.1016/j.forsciint.2013.02.039

220
Isomer 2

3-MeA
PAL-314
3-Methylamphetamine

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

See also PiHKAL: #54 2,5-DMA      

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

Bailey, K; Legault, D. Analysis of the 13C-NMR spectra of mono- and dimethylamphetamines. Anal. Chim. Acta., 1 Jan 1981, 123, 75–82. 654 kB. doi:10.1016/S0003-2670(01)83160-3

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

Power, JD; Clarke, K; McDermott, SD; McGlynn, P; Barry, M; White, C; O’Brien, J; Kavanagh, P. The identification of 4-methylamphetamine and its synthesis by-products in forensic samples. Forensic Sci. Int., 10 May 2013, 228 (1–3), 115–131. 1893 kB. doi:10.1016/j.forsciint.2013.02.039

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

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 2618 kB.

221
Isomer 3

PMeA
4-MA
PAL-313
4-Methylamphetamine
Aptrol

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

See also PiHKAL: #54 2,5-DMA      

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Power, JD; Clarke, K; McDermott, SD; McGlynn, P; Barry, M; White, C; O’Brien, J; Kavanagh, P. The identification of 4-methylamphetamine and its synthesis by-products in forensic samples. Forensic Sci. Int., 10 May 2013, 228 (1–3), 115–131. 1893 kB. doi:10.1016/j.forsciint.2013.02.039

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

Bailey, K; Legault, D. Analysis of the 13C-NMR spectra of mono- and dimethylamphetamines. Anal. Chim. Acta., 1 Jan 1981, 123, 75–82. 654 kB. doi:10.1016/S0003-2670(01)83160-3

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 2618 kB.

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

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

Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta Pharmacol. Toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x

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

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

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

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

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. 1188 kB. doi:10.1021/jm00256a016

2002
Isomer 4

MA
Methamphetamine

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

See also PiHKAL: #14 BOD #66 DOET #109 MDMA #142 PEA
See also TiHKAL: #5 α,O-DMS #8 α,N-DMT #11 α-ET  
See also Pharmacology notes I: p. 134, MA: Subjective analysis

Bianchi, RP; Shah, MN; Rogers, DH; Mrazik, TJ. Laboratory analysis of the conversion of pseudoephedrine to methamphetamine from over-the-counter products. Microgram J., 1 Jan 2005, 3 (1–2), 11–15. 32 kB.

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Martinez, FS; Roesch, DM; Jacobs, JL. Isolation of methamphetamine from 1-(1′,4′-cyclohexadienyl)-2-methylaminopropane (CMP) using potassium permanganate. Microgram J., 1 Jan 2008, 6 (1–2), 46–54. 149 kB.

Lurie, IS; Bozenko, JS; Li, L; Miller, EE; Greenfield, SJ. Chiral separation of methamphetamine and related compounds using capillary electrophoresis with dynamically coated capillaries. Microgram J., 1 Jan 2011, 8 (1), 24–28. 786 kB.

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Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

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Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Rasmussen, N. Making the first anti-depressant: Amphetamine in American medicine, 1929-1950. J. Hist. Med. Allied Sci., 1 Jul 2006, 61 (3), 288–323. 175 kB. doi:10.1093/jhmas/jrj039

Stojanovska, N; Fu, S; Tahtouh, M; Kelly, T; Beavis, A; Kirkbride, KP. A review of impurity profiling and synthetic route of manufacture of methylamphetamine, 3,4-methylenedioxymethylamphetamine, amphetamine, dimethylamphetamine and p-methoxyamphetamine. Forensic Sci. Int., 10 Jan 2013, 224 (1–3), 8–26. 813 kB. doi:10.1016/j.forsciint.2012.10.040

Eshleman, AJ; Wolfrum, KM; Hatfield, MG; Johnson, RA; Murphy, KV; Janowsky, A. Substituted methcathinones differ in transporter and receptor interactions. Biochem. Pharmacol., 15 Jun 2013, 85 (12), 1803–1815. 2164 kB. doi:10.1016/j.bcp.2013.04.004

Dybdal-Hargreaves, NF; Holder, ND; Ottoson, PE; Sweeney, MD; Williams, T. Mephedrone: Public health risk, mechanisms of action, and behavioral effects. Eur. J. Pharmacol., 15 Aug 2013, 714 (1–3), 32–40. 837 kB. doi:10.1016/j.ejphar.2013.05.024

Felice, LJD; Glennon, RA; Negus, SS. Synthetic cathinones: Chemical phylogeny, physiology, and neuropharmacology. Life Sci., 27 Feb 2014, 97 (1), 20–26. 697 kB. doi:10.1016/j.lfs.2013.10.029

Angoa-Pérez, M; Kane, MJ; Herrera-Mundo, N; Francescutti, DM; Kuhn, DM. Effects of combined treatment with mephedrone and methamphetamine or 3,4-methylenedioxymethamphetamine on serotonin nerve endings of the hippocampus. Life Sci., 27 Feb 2014, 97 (1), 31–36. 888 kB. doi:10.1016/j.lfs.2013.07.015

LeBelle, MJ; Savard, C; Dawson, BA; Black, DB; Katyal, LK; Zrcek, F; By, AW. Chiral identification and determination of ephedrine, pseudoephedrine, methamphetamine and metecathinone by gas chromatography and nuclear magnetic resonance. Forensic Sci. Int., 28 Feb 1995, 71 (3), 215–223. 405 kB. doi:10.1016/0379-0738(94)01669-0

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

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

Shulgin, AT. Ice, crank, speed or methamphetamine. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 6 Apr 2005.

Shulgin, AT. MDMA (Ecstasy) v. Methamphetamine. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 15 Feb 2001.

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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

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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

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 Oct 2001, 33 (4), 409–412. 691 kB. doi:10.1080/02791072.2001.10399926

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

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2365
Isomer 5

AEPEA
Phenylisobutylamine
α-Ethylphenethylamine

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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-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

5556
Isomer 6

DMePEA

IUPAC: 2-(3,4-Dimethylphenyl)ethan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: IQXUVSNUSQIQCJ-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-8-3-4-10(5-6-11)7-9(8)2/h3-4,7H,5-6,11H2,1-2H3

PubChem CID: 410083; ChemSpider: 362939

Shulgin Index: #43 DMePEA; Table: 4 Page: 327 Row: 32

Benington, F; Morin, R; Clark, LC. Mescaline analogs. X. 3,4-Dimethyl-, 3,4-dichloro- and 3,5-dimethoxy-4-methyl-β-phenethylamines. J. Org. Chem., 1 Nov 1960, 25 (11), 2066–2067. 286 kB. doi:10.1021/jo01081a626

6003
Isomer 7

N,N-MePEA
DM-PEA

IUPAC: N,N-Dimethyl-2-phenylethan-1-amine

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

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

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

6004
Isomer 8

N-EtPEA

IUPAC: N-Ethyl-2-phenylethan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: WOHOHPONCSKXSQ-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-2-11-9-8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3

PubChem CID: 547324; ChemSpider: 476381

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 4

6008
Isomer 9

β,N-MePEA

IUPAC: N-Methyl-2-phenylpropan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: AUFSOOYCQYDGES-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9(8-11-2)10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3

PubChem CID: 22276; ChemSpider: 21277725

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 8

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

6255
Isomer 10

4-EtPEA

IUPAC: 2-(4-Ethylphenyl)ethan-1-amine

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

6361
Isomer 11

2,3-DMePEA

IUPAC: 2-(2,3-Dimethylphenyl)ethan-1-amine

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

6433
Isomer 12

2,4-DMePEA

IUPAC: 2-(2,4-Dimethylphenyl)ethan-1-amine

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

6808
Isomer 13

2,5-DMePEA

IUPAC: 2-(2,5-Dimethylphenyl)ethan-1-amine

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

6918
Isomer 14

3,5-DMePEA

IUPAC: 2-(3,5-Dimethylphenyl)ethan-1-amine

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

6953
Isomer 15

2,6-DMePEA

IUPAC: 2-(2,6-Dimethylphenyl)ethan-1-amine

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

1559
Isomer 16

β,β-Me-PEA

IUPAC: 2-Methyl-2-phenylpropan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: CWSGTPMVOJFVIF-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-10(2,8-11)9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3

PubChem CID: 210602; ChemSpider: 182543

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

2534
Isomer 17

2-MeMA
2-Methylmethamphetamine

IUPAC: N-Methyl-2-(2-methylphenyl)ethan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: JOFBJXRAJMVOGU-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9-5-3-4-6-10(9)7-8-11-2/h3-6,11H,7-8H2,1-2H3

PubChem CID: 11788692; ChemSpider: 9963366

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

2535
Isomer 18

3-MeMA
3-Methylmethamphetamine

IUPAC: N-Methyl-2-(3-methylphenyl)ethan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: CCKKJKNZCZIBJP-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9-4-3-5-10(8-9)6-7-11-2/h3-5,8,11H,6-7H2,1-2H3

PubChem CID: 22902380; ChemSpider: 14025863

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

1045
Isomer 19

Homoamphetamine

IUPAC: 4-Phenylbutan-2-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: WECUIGDEWBNQJJ-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6,9H,7-8,11H2,1H3

PubChem CID: 31160; ChemSpider: 28910

King, LA. New phenethylamines in Europe. Drug Test. Anal., 20 Nov 2013. 472 kB. doi:10.1002/dta.1570

930
Isomer 20

N-IPr-Benzylamine
N-iPr-Benzylamine

IUPAC: N-Benzylpropan-2-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: LYBKPDDZTNUNNM-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9(2)11-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3

PubChem CID: 66024; ChemSpider: 59415

Sanderson, RM. Identification of N-methylbenzylamine hydrochloride, N-ethylbenzylamine hydrochloride, and N-isopropylbenzylamine hydrochloride. Microgram J., 1 Jan 2008, 6 (1–2), 36–45. 495 kB.

Show all 70 analogues and isomers Show only the one N analogues Show only the five α analogues Show only the one β analogues Show only the one R2 analogues Show only the two R4 analogues Show only the 40 skeleton analogues
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