Go to TiHKAL • info home
Browse the short index of TiHKAL tryptamines. Read book II of TiHKAL
Search for tryptamines and related structures Beyond TiHKAL—Selected writings by Sasha and others. Explore tryptamine structures and analogues
The alkaloids of the peyote cactus. How TiHKAL • info differs from the printed version
Go to PiHKAL • info home
You are currently exploring NM-2-AI.
To explore a different substance, type its name: Help
NM-2-AI; N-Methyl-2-aminoindane
1327
Variant: N skeleton isomers all
Analogues: 10 93 8 111

IUPAC: N-Methyl-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C10H13N/c1-11-10-6-8-4-2-3-5-9(8)7-10/h2-5,10-11H,6-7H2,1H3

PubChem CID: 15023225; ChemSpider: 13566342

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

10 N analogues:
2357
Analogue 1: Removing Methyl at N

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

1328
Analogue 2: Substituting Ethyl for Methyl at N

NE-2-AI
N-Ethyl-2-aminoindane

IUPAC: N-Ethyl-2,3-dihydro-1H-inden-2-amine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: RAJHFMSNMQFOPU-UHFFFAOYSA-N

InChI=1S/C11H15N/c1-2-12-11-7-9-5-3-4-6-10(9)8-11/h3-6,11-12H,2,7-8H2,1H3

PubChem CID: 12452138; ChemSpider: 10635088

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

1329
Analogue 3: Substituting n-Propyl for Methyl at N

NP-2-AI
N-Propyl-2-aminoindane

IUPAC: N-Propyl-2,3-dihydro-1H-inden-2-amine

Formula: C12H17N Molecular weight: 175.27008 g/mol InChI Key: OYJSAKGCKMRLQO-UHFFFAOYSA-N

InChI=1S/C12H17N/c1-2-7-13-12-8-10-5-3-4-6-11(10)9-12/h3-6,12-13H,2,7-9H2,1H3

PubChem CID: 17221237; ChemSpider: 13775926

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

1330
Analogue 4: Substituting Isopropyl for Methyl at N

NIP-2-AI
N-Isopropyl-2-aminoindane

IUPAC: N-(Propan-2-yl)-2,3-dihydro-1H-inden-2-amine

Formula: C12H17N Molecular weight: 175.27008 g/mol InChI Key: RPGLUMRDPMBBBQ-UHFFFAOYSA-N

InChI=1S/C12H17N/c1-9(2)13-12-7-10-5-3-4-6-11(10)8-12/h3-6,9,12-13H,7-8H2,1-2H3

PubChem CID: 18790309; ChemSpider: 19330265

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

1331
Analogue 5: Substituting n-Butyl for Methyl at N

NB-2-AI
N-Butyl-2-aminoindane

IUPAC: N-Butyl-2,3-dihydro-1H-inden-2-amine

Formula: C13H19N Molecular weight: 189.29666 g/mol InChI Key: USGDCMIVRWBLEQ-UHFFFAOYSA-N

InChI=1S/C13H19N/c1-2-3-8-14-13-9-11-6-4-5-7-12(11)10-13/h4-7,13-14H,2-3,8-10H2,1H3

PubChem CID: 43512786; ChemSpider: 25045448

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

1332
Analogue 6: Substituting Dimethyl for Methyl at N

DM-2-AI
N,N-Dimethyl-2-aminoindane

IUPAC: N,N-Dimethyl-2,3-dihydro-1H-inden-2-amine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: JHJKWSLLPQWCDF-UHFFFAOYSA-N

InChI=1S/C11H15N/c1-12(2)11-7-9-5-3-4-6-10(9)8-11/h3-6,11H,7-8H2,1-2H3

PubChem CID: 3016704; ChemSpider: 2284609

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

1333
Analogue 7: Substituting Diethyl for Methyl at N

DE-2-AI
N,N-Diethyl-2-aminoindane

IUPAC: N,N-Diethyl-2,3-dihydro-1H-inden-2-amine

Formula: C13H19N Molecular weight: 189.29666 g/mol InChI Key: IPKWICPQIRRGCU-UHFFFAOYSA-N

InChI=1S/C13H19N/c1-3-14(4-2)13-9-11-7-5-6-8-12(11)10-13/h5-8,13H,3-4,9-10H2,1-2H3

PubChem CID: 44377347; ChemSpider: 25059704

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

1334
Analogue 8: Substituting Di-n-propyl for Methyl at N

DP-2-AI
N,N-Dipropyl-2-aminoindane

IUPAC: N,N-Dipropyl-2,3-dihydro-1H-inden-2-amine

Formula: C15H23N Molecular weight: 217.34982 g/mol InChI Key: LEACNHXRZNVYRP-UHFFFAOYSA-N

InChI=1S/C15H23N/c1-3-9-16(10-4-2)15-11-13-7-5-6-8-14(13)12-15/h5-8,15H,3-4,9-12H2,1-2H3

PubChem CID: 130402; ChemSpider: 115377

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

1335
Analogue 9: Substituting Di-n-butyl for Methyl at N

DB-2-AI
N,N-Dibutyl-2-aminoindane

IUPAC: N,N-Dibutyl-2,3-dihydro-1H-inden-2-amine

Formula: C17H27N Molecular weight: 245.40298 g/mol InChI Key: KPEQEOIOBDNTTE-UHFFFAOYSA-N

InChI=1S/C17H27N/c1-3-5-11-18(12-6-4-2)17-13-15-9-7-8-10-16(15)14-17/h7-10,17H,3-6,11-14H2,1-2H3

PubChem CID: 44377160; ChemSpider: 25047505

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

1336
Analogue 10: Substituting Isopropyl and Methyl for Methyl at N

MIP-2-AI
N-Isopropyl-N-methyl-2-aminoindane

IUPAC: N-Methyl-N-(propan-2-yl)-2,3-dihydro-1H-inden-2-amine

Formula: C13H19N Molecular weight: 189.29666 g/mol InChI Key: VIKSKFWKHBZMCS-UHFFFAOYSA-N

InChI=1S/C13H19N/c1-10(2)14(3)13-8-11-6-4-5-7-12(11)9-13/h4-7,10,13H,8-9H2,1-3H3

PubChem CID: 44377147; ChemSpider: 25056058

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

93 skeleton analogues:
142
Analogue 1: With 2-Phenylethan-1-amine skeleton

PEA
β-PEA
2-PEA
β-Phenethylamine
Phenethylamine

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

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

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.

2000
Analogue 2: With 2-Phenylethan-1-amine skeleton

Ephedrine
(1R,2S)-2-Methylamino-1-phenylpropan-1-ol

IUPAC: (1R,2S)-2-(Methylamino)-1-phenylpropan-1-ol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: KWGRBVOPPLSCSI-WPRPVWTQSA-N

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

PubChem CID: 9294; ChemSpider: 8935; Erowid: Ephedrine; Wikipedia: Ephedrine

Shulgin Index: Table: 2 Page: 318 Row: 25

See also PiHKAL: #42 Ψ-2C-T-4 #142 PEA    
See also TiHKAL: #8 α,N-DMT      

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

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

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

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

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.

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.

2001
Analogue 3: With 2-Phenylethan-1-amine skeleton

Pseudoephedrine
(1S,2S)-2-Methylamino-1-phenylpropan-1-ol

IUPAC: (1S,2S)-2-(Methylamino)-1-phenylpropan-1-ol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: KWGRBVOPPLSCSI-PEHGTWAWSA-N

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10?/m0/s1

PubChem CID: 7028; ChemSpider: 6761; Wikipedia: Pseudoephedrine

Shulgin Index: Table: 2 Page: 318 Row: 26

See also PiHKAL: #42 Ψ-2C-T-4      

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

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

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

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

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.

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.

2002
Analogue 4: With 2-Phenylethan-1-amine skeleton

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

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

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.

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.

Fultz, BA; Mann, JA; Gardne, EA. Methamphetamine contaminated currency in the Birmingham, Alabama metropolitan area. Microgram J., 1 Jan 2012, 9 (2), 57–60. 209 kB.

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.

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.

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

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

Cameron, K; Kolanos, R; Vekariya, R; Felice, LD; Glennon, RA. Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of “bath salts,” produce opposite effects at the human dopamine transporter. Psychopharmacology, 1 Jun 2013, 227 (3), 493–499. 190 kB. doi:10.1007/s00213-013-2967-2

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

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

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

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

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. 691 kB. doi:10.1080/02791072.2001.10399926

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

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

2003
Analogue 5: With 2-Amino-1-phenylethanone skeleton

METHCATH
Methcathinone
α-Methylaminopropiophenone
Ephedrone

IUPAC: 2-(Methylamino)-1-phenylpropan-1-one

Formula: C10H13NO Molecular weight: 163.21632 g/mol InChI Key: LPLLVINFLBSFRP-UHFFFAOYSA-N

InChI=1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3

PubChem CID: 1576; ChemSpider: 1519; Erowid: Cathinone & Methcathinone; Wikipedia: Methcathinone

Shulgin Index: #92 METHCATH; Table: 2 Page: 318 Row: 33

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. 4162 kB.

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.

Cozzi, NV; Shulgin, AT; Ruoho, AE. Methcathinone (MCAT) and 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit [3H]serotonin uptake into human platelets. Amer. Chem. Soc. Div. Med. Chem. Abs., 1 Jan 1998, 215, 152. 11 kB.

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

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

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

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

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

Cozzi, NV; Brandt, SD; Daley, PF; Partilla, JS; Rothman, RB; Tulzer, A; Sitte, HH; Baumann, MH. Pharmacological examination of trifluoromethyl ring-substituted methcathinone analogs. Eur. J. Pharmacol., 15 Jan 2013, 699 (1–3), 180–187. 590 kB. doi:10.1016/j.ejphar.2012.11.008

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

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

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

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

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

Cameron, K; Kolanos, R; Vekariya, R; Felice, LD; Glennon, RA. Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of “bath salts,” produce opposite effects at the human dopamine transporter. Psychopharmacology, 1 Jun 2013, 227 (3), 493–499. 190 kB. doi:10.1007/s00213-013-2967-2

Foley, KF; Cozzi, NV. Novel aminopropiophenones as potential antidepressants. Drug Develop. Res., 1 Dec 2003, 60 (4), 252–260. 1588 kB. doi:10.1002/ddr.10297

2004
Analogue 6: 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      

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. 4162 kB.

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

2006
Analogue 7: With 2-Phenylethan-1-amine skeleton

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

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

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. Et toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x

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.

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

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 ?-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

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

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

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.

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

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

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.

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

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

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

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

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.

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

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

2114
Analogue 8: 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.

2121
Analogue 9: With Phenylethyl-cyclic-amine skeleton

Prolintane
1-(1-Benzylbutyl)pyrrolidine

IUPAC: 1-(1-Phenylpentan-2-yl)pyrrolidine

Formula: C15H23N Molecular weight: 217.34982 g/mol InChI Key: OJCPSBCUMRIPFL-UHFFFAOYSA-N

InChI=1S/C15H23N/c1-2-8-15(16-11-6-7-12-16)13-14-9-4-3-5-10-14/h3-5,9-10,15H,2,6-8,11-13H2,1H3

PubChem CID: 14592; ChemSpider: 13930; Wikipedia: Prolintane

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

2341
Analogue 10: With 2-Cyclic-amine-1-phenylethanone skeleton

α-PBP
α-Pyrrolidinobutrophenone

IUPAC: 1-Phenyl-2-(pyrrolidin-1-yl)butan-1-one

Formula: C14H19NO Molecular weight: 217.30676 g/mol InChI Key: GSESDIFGJCCBHN-UHFFFAOYSA-N

InChI=1S/C14H19NO/c1-2-13(15-10-6-7-11-15)14(16)12-8-4-3-5-9-12/h3-5,8-9,13H,2,6-7,10-11H2,1H3

PubChem CID: 23199082; Wikipedia: Alpha-Pyrrolidinobutiophenone

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

2340
Analogue 11: With 2-Amino-1-phenylethanone skeleton

MABP
Buphedrone
α-(Methylamino)butyrophenone

IUPAC: 2-(Methylamino)-1-phenylbutan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: DDPMGIMJSRUULN-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-3-10(12-2)11(13)9-7-5-4-6-8-9/h4-8,10,12H,3H2,1-2H3

PubChem CID: 53249194; ChemSpider: 26286946; Wikipedia: Buphedrone

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

Maheux, CR; Copeland, CR. Chemical analysis of two new designer drugs: Buphedrone and pentedrone. Drug Test. Anal., 1 Jan 2012, 4 (1), 17–23. 314 kB. doi:10.1002/dta.385

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

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

2342
Analogue 12: With 2-Cyclic-amine-1-phenylethanone skeleton

α-PVP
α-Pyrrolidinopentiophenone
α-Pyrrolidinovalerophenone

IUPAC: 1-Phenyl-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C15H21NO Molecular weight: 231.33334 g/mol InChI Key: YDIIDRWHPFMLGR-UHFFFAOYSA-N

InChI=1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3

PubChem CID: 11148955; ChemSpider: 9324063; Wikipedia: Alpha-Pyrrolidinopentiophenone

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

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

Casale, JF; Hays, PA. The characterization of α-pyrrolidinopentiophenone. Microgram J., 1 Jan 2012, 9 (1), 33–38. 1194 kB.

400
Analogue 13: 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 ?-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

2365
Analogue 14: With 2-Phenylethan-1-amine skeleton

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 ?-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

2371
Analogue 15: With 2-Phenylethan-1-amine skeleton

N-MePEA
N-Methylphenethylamine

IUPAC: N-Methyl-2-phenylethanamine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: SASNBVQSOZSTPD-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-10-8-7-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3

PubChem CID: 11503; ChemSpider: 11019; Wikipedia: Methylphenethylamine

Shulgin Index: #89 N-MePEA; Table: 2 Page: 318 Row: 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

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

5554
Analogue 16: With 2-Phenylethan-1-amine skeleton

β-Me-PEA
β-Methylphenethylamine

IUPAC: 2-Phenylpropan-1-amine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: AXORVIZLPOGIRG-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3

PubChem CID: 11398; ChemSpider: 10920; Wikipedia: Beta-Methylphenethylamine

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

2405
Analogue 17: With 2-Phenylethan-1-amine skeleton

β-Methoxyamphetamine

IUPAC: 1-Methoxy-1-phenylpropan-2-amine

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: XNYRQJJPTRMQBG-UHFFFAOYSA-N

InChI=1S/C10H15NO/c1-8(11)10(12-2)9-6-4-3-5-7-9/h3-8,10H,11H2,1-2H3

PubChem CID: 12843489; ChemSpider: 28169264

2393
Analogue 18: With 2-Phenylethan-1-amine skeleton

Norephedrine
nor-Ephedrine

IUPAC: (1R,2S)-2-Amino-1-phenylpropan-1-ol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: DLNKOYKMWOXYQA-CBAPKCEASA-N

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1

PubChem CID: 4786; ChemSpider: 4622

Shulgin Index: Table: 2 Page: 318 Row: 23

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

Osorio-Olivares, M; Rezende, MC; Sepúlveda-Boza, S; Cassels, BK; Fierro, A. MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position. Bioorg. Med. Chem., 1 Jan 2004, 12 (15), 4055–4066. 412 kB. doi:10.1016/j.bmc.2004.05.033

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

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

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

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

2378
Analogue 19: With 2-Phenylethan-1-amine skeleton

Phenibut

IUPAC: 4-Amino-3-phenylbutanoic acid

Formula: C10H13NO2 Molecular weight: 179.21572 g/mol InChI Key: DAFOCGYVTAOKAJ-UHFFFAOYSA-N

InChI=1S/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)

PubChem CID: 14113; ChemSpider: 13491; Erowid: Phenibut; Wikipedia: Phenibut

801
Analogue 20: 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

904
Analogue 21: With 1-Benzylpiperazine skeleton

MBZP

IUPAC: 1-Benzyl-4-methylpiperazine

Formula: C12H18N2 Molecular weight: 190.28472 g/mol InChI Key: MLJOKPBESJWYGL-UHFFFAOYSA-N

InChI=1S/C12H18N2/c1-13-7-9-14(10-8-13)11-12-5-3-2-4-6-12/h2-6H,7-11H2,1H3

PubChem CID: 763557; ChemSpider: 667589; Wikipedia: Methylbenzylpiperazine

Shulgin Index: Table: 9 Page: 357 Row: 20

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

903
Analogue 22: 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

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

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.

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

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

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

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

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

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

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

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

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

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

902
Analogue 23: With Phenylmethanamine skeleton

1-PEA
α-PEA
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

901
Analogue 24: 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

602
Analogue 25: With 3-Phenylpropan-1-amine skeleton

homo-β,N-MePEA

IUPAC: N,2-Dimethyl-3-phenylpropan-1-amine

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

InChI=1S/C11H17N/c1-10(9-12-2)8-11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3

PubChem CID: 21714712

Shulgin Index: See #107 PEA; Table: 10 Page: 358 Row: 9

601
Analogue 26: 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

2434
Analogue 27: With 2-Amino-1-phenylethanone skeleton

Pentedrone

IUPAC: 2-(Methylamino)-1-phenylpentan-1-one

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

InChI=1S/C12H17NO/c1-3-7-11(13-2)12(14)10-8-5-4-6-9-10/h4-6,8-9,11,13H,3,7H2,1-2H3

PubChem CID: 57501499; ChemSpider: 26286729

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

Maheux, CR; Copeland, CR. Chemical analysis of two new designer drugs: Buphedrone and pentedrone. Drug Test. Anal., 1 Jan 2012, 4 (1), 17–23. 314 kB. doi:10.1002/dta.385

Westphal, F; Junge, T; Girreser, U; Greibl, W; Doering, C. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 157–167. 853 kB. doi:10.1016/j.forsciint.2011.10.045

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

6007
Analogue 28: 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

6008
Analogue 29: With 2-Phenylethan-1-amine skeleton

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.

6010
Analogue 30: With 2-Phenylethan-1-amine skeleton

β-HO-PEA

IUPAC: 2-Amino-1-phenylethanol

Formula: C8H11NO Molecular weight: 137.17904 g/mol InChI Key: ULSIYEODSMZIPX-UHFFFAOYSA-N

InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2

PubChem CID: 1000; ChemSpider: 975

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 10

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

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

6012
Analogue 31: 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

6013
Analogue 32: With 2-Amino-1-phenylethanone skeleton

MAA

IUPAC: 2-(Methylamino)-1-phenylethanone

Formula: C9H11NO Molecular weight: 149.18974 g/mol InChI Key: VVFCJVLORNFVHI-UHFFFAOYSA-N

InChI=1S/C9H11NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,10H,7H2,1H3

PubChem CID: 416157; ChemSpider: 368424

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 13

6024
Analogue 33: With 2-Phenylethan-1-amine skeleton

Norpseudoephdrine
nor-Pseudoephdrine

IUPAC: (1S,2S)-2-Amino-1-phenylpropan-1-ol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: DLNKOYKMWOXYQA-IONNQARKSA-N

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1

PubChem CID: 54463712; ChemSpider: 390189

Shulgin Index: Table: 2 Page: 318 Row: 24

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

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

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

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

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

6028
Analogue 34: 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

6031
Analogue 35: 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 36: 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 37: 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

6056
Analogue 38: With 2-Phenylethan-1-amine skeleton

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

6057
Analogue 39: With 2-Phenylethan-1-amine skeleton

Phentermine

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

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

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

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

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

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.

6058
Analogue 40: With 2-Phenylethan-1-amine skeleton

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

2461
Analogue 41: With 2-Phenylethan-1-amine skeleton

β-Aminoamphetamine

IUPAC: 1-Phenylpropane-1,2-diamine

Formula: C9H14N2 Molecular weight: 150.22086 g/mol InChI Key: PRCXGQJVEKZKQR-UHFFFAOYSA-N

InChI=1S/C9H14N2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9H,10-11H2,1H3

PubChem CID: 12475829; ChemSpider: 13341018

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

461
Analogue 42: With 2-Phenylethan-1-amine skeleton

β-DFA

IUPAC: 1,1-Difluoro-1-phenylpropan-2-amine

Formula: C9H11F2N Molecular weight: 171.1871464 g/mol InChI Key: CTOGXYQJJYYTRC-UHFFFAOYSA-N

InChI=1S/C9H11F2N/c1-7(12)9(10,11)8-5-3-2-4-6-8/h2-7H,12H2,1H3

PubChem CID: 12570687; ChemSpider: 10324996

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

460
Analogue 43: With 2-Phenylethan-1-amine skeleton

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

459
Analogue 44: With 2-Phenylethan-1-amine skeleton

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 45: With 2-Phenylethan-1-amine skeleton

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

2462
Analogue 46: 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 47: 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 48: 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 49: 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 ?-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

557
Analogue 50: With Benzyl-cyclic-amine skeleton

Desoxypipradrol
2-DPMP
2-Diphenylmethylpiperidine;

IUPAC: 2-(Diphenylmethyl)piperidine

Formula: C18H21N Molecular weight: 251.36604 g/mol InChI Key: RWTNXJXZVGHMGI-UHFFFAOYSA-N

InChI=1S/C18H21N/c1-3-9-15(10-4-1)18(16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17-19H,7-8,13-14H2

PubChem CID: 160506; ChemSpider: 141045

Corkery, JM; Elliott, S; Schifano, F; Corazza, O; Ghodse, AH. 2-DPMP (desoxypipradrol, 2-benzhydrylpiperidine, 2-phenylmethylpiperidine) and D2PM (diphenyl-2-pyrrolidin-2-yl-methanol, diphenylprolinol): A preliminary review. Prog. Neuro-Psychopharmacol. Biol. Psych., 3 Dec 2012, 39 (2), 253–258. 347 kB. doi:10.1016/j.pnpbp.2012.05.021

Wood, DM; Dargan, PI. Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP). Clin. Toxicol., 1 Sep 2012, 50 (8), 727–732. 117 kB. doi:10.3109/15563650.2012.716158

Iversen, LL. Consideration of desoxypipradrol (2-DPMP) and related pipradrol compounds, Advisory Council on the Misuse of Drugs, 13 Sep 2011.

558
Analogue 51: With Benzyl-cyclic-amine skeleton

Pipradrol

IUPAC: Diphenyl(piperidin-2-yl)methanol

Formula: C18H21NO Molecular weight: 267.36544 g/mol InChI Key: XSWHNYGMWWVAIE-UHFFFAOYSA-N

InChI=1S/C18H21NO/c20-18(15-9-3-1-4-10-15,16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17,19-20H,7-8,13-14H2

PubChem CID: 10083; ChemSpider: 9681

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

559
Analogue 52: With Benzyl-cyclic-amine skeleton

Desoxy-D2PM
2-Diphenylmethylpyrrolidine

IUPAC: 2-(Diphenylmethyl)pyrrolidine

Formula: C17H19N Molecular weight: 237.33946 g/mol InChI Key: OXOBKZZXZVFOBB-UHFFFAOYSA-N

InChI=1S/C17H19N/c1-3-8-14(9-4-1)17(16-12-7-13-18-16)15-10-5-2-6-11-15/h1-6,8-11,16-18H,7,12-13H2

PubChem CID: 1295; ChemSpider: 1256

Paoli, GD; Brandt, SD; Pounder, DJ. Analytical characterization and rapid determination of 2-(diphenylmethyl)pyrrolidine in blood and application to an internet product. J. Chromatogr. B, 1 Dec 2011, 879 (31), 3771–3774. 353 kB. doi:10.1016/j.jchromb.2011.10.014

560
Analogue 53: With Benzyl-cyclic-amine skeleton

D2PM
Diphenylprolinol

IUPAC: Diphenyl(pyrrolidin-2-yl)methanol

Formula: C17H19NO Molecular weight: 253.33886 g/mol InChI Key: OGCGXUGBDJGFFY-UHFFFAOYSA-N

InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2

PubChem CID: 204386; ChemSpider: 177034

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

Lidder, S; Dargan, PI; Sexton, M; Button, J; Ramsey, J; Holt, DW; Wood, DM. Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol [D2PM]). J. Med. Toxicol., 1 Sep 2008, 4 (3), 167–169. 164 kB. doi:10.1007/BF03161195

Corkery, JM; Elliott, S; Schifano, F; Corazza, O; Ghodse, AH. 2-DPMP (desoxypipradrol, 2-benzhydrylpiperidine, 2-phenylmethylpiperidine) and D2PM (diphenyl-2-pyrrolidin-2-yl-methanol, diphenylprolinol): A preliminary review. Prog. Neuro-Psychopharmacol. Biol. Psych., 3 Dec 2012, 39 (2), 253–258. 347 kB. doi:10.1016/j.pnpbp.2012.05.021

Wood, DM; Dargan, PI. Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP). Clin. Toxicol., 1 Sep 2012, 50 (8), 727–732. 117 kB. doi:10.3109/15563650.2012.716158

561
Analogue 54: 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

562
Analogue 55: 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.

565
Analogue 56: With Benzyl-cyclic-amine skeleton

Methylphenidate

IUPAC: Methyl phenyl(piperidin-2-yl)acetate

Formula: C14H19NO2 Molecular weight: 233.30616 g/mol InChI Key: DUGOZIWVEXMGBE-UHFFFAOYSA-N

InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3

PubChem CID: 4158; ChemSpider: 4015

Griffiths, RR; Richards, WA; McCann, U; Jesse, R. Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology, 1 Aug 2006, 187 (3), 268–283. 342 kB. doi:10.1007/s00213-006-0457-5

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

566
Analogue 57: With Benzyl-cyclic-amine skeleton

Ethylphenidate

IUPAC: Ethyl phenyl(piperidin-2-yl)acetate

Formula: C15H21NO2 Molecular weight: 247.33274 g/mol InChI Key: AIVSIRYZIBXTMM-UHFFFAOYSA-N

InChI=1S/C15H21NO2/c1-2-18-15(17)14(12-8-4-3-5-9-12)13-10-6-7-11-16-13/h3-5,8-9,13-14,16H,2,6-7,10-11H2,1H3

PubChem CID: 3080846; ChemSpider: 2338571

Casale, JF; Hays, PA. Ethylphenidate: An analytical profile. Microgram J., 2011, 8 (2), 58–61. 906 kB.

1235
Analogue 58: 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

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

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

542
Analogue 59: 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 60: 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 61: 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

1317
Analogue 62: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Methyl-2-aminotetralin

IUPAC: N-Methyl-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: NZARMFRLPAOETR-UHFFFAOYSA-N

InChI=1S/C11H15N/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-5,11-12H,6-8H2,1H3

PubChem CID: 13579644; ChemSpider: 10437468

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

1339
Analogue 63: With 2-Phenylethanol skeleton

1-Phenyl-2-propanol

IUPAC: 1-Phenylpropan-2-ol

Formula: C9H12O Molecular weight: 136.19098 g/mol InChI Key: WYTRYIUQUDTGSX-UHFFFAOYSA-N

InChI=1S/C9H12O/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8,10H,7H2,1H3

PubChem CID: 94185; ChemSpider: 84999

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

1434
Analogue 64: 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 65: 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 66: 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 67: 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

1442
Analogue 68: With Phenylmethanamine skeleton

N-M-1-PEA
α,N-DMBA

IUPAC: N-Methyl-1-phenylethanamine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: RCSSHZGQHHEHPZ-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-8(10-2)9-6-4-3-5-7-9/h3-8,10H,1-2H3

PubChem CID: 577403; ChemSpider: 501944

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

1471
Analogue 69: 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

1482
Analogue 70: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-Methyl-2-phenylcyclopropanamine

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

InChI=1S/C10H13N/c1-11-10-7-9(10)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3

PubChem CID: 12682037

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 71: 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 72: 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 73: 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 74: 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 75: 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 76: 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

1512
Analogue 77: With 1-Benzylcyclopropan-1-amine skeleton

IUPAC: 1-Benzyl-N-methylcyclopropanamine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: BGOXWIGSAFWNSY-UHFFFAOYSA-N

InChI=1S/C11H15N/c1-12-11(7-8-11)9-10-5-3-2-4-6-10/h2-6,12H,7-9H2,1H3

PubChem CID: 21748398

1558
Analogue 78: With 2-Phenylethan-1-amine skeleton

2,3-Cl-PEA

IUPAC: 2-(2,3-Dichlorophenyl)ethanamine

Formula: C8H9Cl2N Molecular weight: 190.06976 g/mol InChI Key: WWRLSNWKOZHYIY-UHFFFAOYSA-N

InChI=1S/C8H9Cl2N/c9-7-3-1-2-6(4-5-11)8(7)10/h1-3H,4-5,11H2

PubChem CID: 2734758; ChemSpider: 2016502

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

1559
Analogue 79: With 2-Phenylethan-1-amine skeleton

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

1561
Analogue 80: With 2-Phenylethan-1-amine skeleton

β-iPr-PEA

IUPAC: 3-Methyl-2-phenylbutan-1-amine

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

InChI=1S/C11H17N/c1-9(2)11(8-12)10-6-4-3-5-7-10/h3-7,9,11H,8,12H2,1-2H3

PubChem CID: 9880217; ChemSpider: 8055893

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

1562
Analogue 81: With 2-Phenylethan-1-amine skeleton

DPEA

IUPAC: 2,2-Diphenylethanamine

Formula: C14H15N Molecular weight: 197.2756 g/mol InChI Key: RXMTUVIKZRXSSM-UHFFFAOYSA-N

InChI=1S/C14H15N/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11,15H2

PubChem CID: 77575; ChemSpider: 69980

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

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

2526
Analogue 82: With Phenylacetaldehyde skeleton

Isoethcathinone

IUPAC: 1-(Ethylamino)-1-phenylpropan-2-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: GHVCNLDRNVGRJP-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-3-12-11(9(2)13)10-7-5-4-6-8-10/h4-8,11-12H,3H2,1-2H3

PubChem CID: 12403217

McDermott, SD; Power, JD; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030

2527
Analogue 83: With Phenylacetaldehyde skeleton

Isopentedrone

IUPAC: 1-(Methylamino)-1-phenylpentan-2-one

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

InChI=1S/C12H17NO/c1-3-7-11(14)12(13-2)10-8-5-4-6-9-10/h4-6,8-9,12-13H,3,7H2,1-2H3

Westphal, F; Junge, T; Girreser, U; Greibl, W; Doering, C. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 157–167. 853 kB. doi:10.1016/j.forsciint.2011.10.045

2759
Analogue 84: 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 85: 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 86: 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

1044
Analogue 87: With Phenylmethanamine skeleton

α-Et-BA
1-PPA
1-Phenylpropanamine

IUPAC: 1-Phenylpropan-1-amine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: AQFLVLHRZFLDDV-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-2-9(10)8-6-4-3-5-7-8/h3-7,9H,2,10H2,1H3

PubChem CID: 18054; ChemSpider: 17057

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

1027
Analogue 88: 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

1018
Analogue 89: With 2-Phenylethan-1-amine skeleton

Phenylpropanolmethylamine

IUPAC: 2-(Methylamino)-1-phenylpropan-1-ol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: KWGRBVOPPLSCSI-UHFFFAOYSA-N

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3

PubChem CID: 5032; ChemSpider: 4856

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.

1017
Analogue 90: With 2-Phenylethan-1-amine skeleton

Phenylpropanolamine

IUPAC: 2-Amino-1-phenylpropan-1-ol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: DLNKOYKMWOXYQA-UHFFFAOYSA-N

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3

PubChem CID: 4786; ChemSpider: 4622

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.

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.

1015
Analogue 91: With Phenylethyl-cyclic-amine skeleton

MT-45

IUPAC: 1-Cyclohexyl-4-(1,2-diphenylethyl)piperazine

Formula: C24H32N2 Molecular weight: 348.52428 g/mol InChI Key: IGBRRSIHEGCUEN-UHFFFAOYSA-N

InChI=1S/C24H32N2/c1-4-10-21(11-5-1)20-24(22-12-6-2-7-13-22)26-18-16-25(17-19-26)23-14-8-3-9-15-23/h1-2,4-7,10-13,23-24H,3,8-9,14-20H2

Wikipedia: MT-45

Uchiyama, N; Matsuda, S; Kawamura, M; Kikura-Hanajiri, R; Goda, Y. Identification of two new-type designer drugs, piperazine derivative MT-45 (I-C6) and synthetic peptide Noopept (GVS-111), with synthetic cannabinoid A-834735, cathinone derivative 4-methoxy-α-PVP, and phenethylamine derivative 4-methylbuphedrine from illegal products. Forensic Toxicol., 1 Jan 2014, 32 (1), 9–18. 678 kB. doi:10.1007/s11419-013-0194-5

929
Analogue 92: With Phenylmethanamine skeleton

N-Et-Benzylamine
N-Et-Benzylamine

IUPAC: N-Benzylethanamine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: HVAAHUDGWQAAOJ-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-2-10-8-9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3

PubChem CID: 84352; ChemSpider: 76094

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.

1098
Analogue 93: With 2-Cyclic-amine-1-phenylethanone skeleton

PV8

IUPAC: 1-Phenyl-2-(pyrrolidin-1-yl)heptan-1-one

Formula: C17H25NO Molecular weight: 259.3865 g/mol InChI Key: DLRWKNLMJAIFQB-UHFFFAOYSA-N

InChI=1S/C17H25NO/c1-2-3-5-12-16(18-13-8-9-14-18)17(19)15-10-6-4-7-11-15/h4,6-7,10-11,16H,2-3,5,8-9,12-14H2,1H3

Eight isomers:
400
Isomer 1

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 ?-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

1471
Isomer 2

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

1478
Isomer 3

IUPAC: 2-(4-Methylphenyl)cyclopropanamine

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

InChI=1S/C10H13N/c1-7-2-4-8(5-3-7)9-6-10(9)11/h2-5,9-10H,6,11H2,1H3

PubChem CID: 22174890; ChemSpider: 11209839

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

1482
Isomer 4

IUPAC: N-Methyl-2-phenylcyclopropanamine

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

InChI=1S/C10H13N/c1-11-10-7-9(10)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3

PubChem CID: 12682037

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
Isomer 5

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
Isomer 6

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

1500
Isomer 7

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

1511
Isomer 8

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

Show all 111 analogues and isomers Show only the 10 N analogues Show only the 93 skeleton analogues
Page updated 21 April 2014 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·