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

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

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

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

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

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

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

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

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

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; 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

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

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

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

Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. doi:10.1124/jpet.103.053975

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

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.

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.

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

Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. doi:10.1016/0091-3057(94)00348-3

Dal Cason, TA; Young, R; Glennon, RA. Cathinone: An investigation of several N-alkyl and methylenedioxy-substituted analogs. Pharmacol. Biochem. Behav., 1 Jan 1997, 58 (4), 1109–1116. 97 kB. doi:10.1016/S0091-3057(97)00323-7

Archer, RP. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1355 kB. doi:10.1016/j.forsciint.2008.11.013

Gambaro, V; Arnoldi, S; Colombo, ML; Dell’Acqua, L; Guerrini, K; Roda, G. Determination of the active principles of Catha Edulis: Quali-quantitative analysis of cathinone, cathine, and phenylpropanolamine. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 87–92. 479 kB. doi:10.1016/j.forsciint.2011.09.028

Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. doi:10.1124/jpet.103.053975

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

Toole, KE; Fu, S; Shimmon, RG; Kraymen, M; Taflaga, S. Color tests for the preliminary identification of methcathinone and analogues of methcathinone. Microgram J., 2012, 9 (1), 27–32. 496 kB.

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

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

Maurer, HH; Kraemer, T; Springer, D; Staack, RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (Ecstasy), piperazine, and pyrrolidinophenone types. A synopsis. Ther. Drug Monit., 1 Apr 2004, 26 (2), 127–131. 121 kB.

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

Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. doi:10.2174/1389200054021825

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

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

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009

Barfknecht, CF; Nichols, DE; Rusterholz, DB; Long, JP; Engelbrecht, JA; Beaton, JM; Bradley, RJ; Dyer, DC. Potential psychotomimetics. 2-Amino-1,2,3,4-tetrahydronaphthalene analogs. J. Med. Chem., 1 Jan 1973, 16, (7), 804–808. 614 kB. doi:10.1021/jm00265a013

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

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

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

BZP

IUPAC: 1-Benzylpiperazine

Formula: C11H16N2 Molecular weight: 176.25814 g/mol InChI Key: IQXXEPZFOOTTBA-UHFFFAOYSA-N

InChI=1S/C11H16N2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h1-5,12H,6-10H2

PubChem CID: 75994; ChemSpider: 68493; Wikipedia: Benzylpiperazine

Shulgin Index: Table: 9 Page: 357 Row: 19

Schep, LJ; Slaughter, RJ; Temple, WA; Gee, P. Comments on BZP and New Zealand’s alternative approach to prohibition. Drug Test. Anal., 1 Jan 2012, 4 (1), 57. 47 kB. doi:10.1002/dta.356

Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3),. 1364 kB. doi:10.1016/j.forsciint.2011.08.005

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Baumann, MH; Clark, RD; Budzynski, AG; Partilla, JS; Blough, BE; Rothman, RB. N-Substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or ‘Ecstasy’). Neuropsychopharmacology, 1 Mar 2005, 30 (3), 550–560. 184 kB. doi:10.1038/sj.npp.1300585

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. doi:10.2174/1389200054021825

Anon. Report on the risk assessment of BZP in the framework of the Council decision on new psychoactive substances, European Monitoring Centre for Drugs and Drug Addiction, 2009. doi:10.2810/44197

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

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

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

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

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

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

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

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

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

cPr-PEA

IUPAC: 2-Phenylcyclopropanamine

Formula: C9H11N Molecular weight: 133.19034 g/mol InChI Key: AELCINSCMGFISI-UHFFFAOYSA-N

InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2

PubChem CID: 5530; ChemSpider: 5329

Shulgin Index: See #107 PEA; Table: 2 Page: 319 Row: 5

Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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

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

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

2-ADN

IUPAC: 1,2-Dihydronaphthalen-2-amine

Formula: C10H11N Molecular weight: 145.20104 g/mol InChI Key: SHLZSYAMFQNEOF-UHFFFAOYSA-N

InChI=1S/C10H11N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-6,10H,7,11H2

PubChem CID: 133605; ChemSpider: 117856; Wikipedia: 2-Amino-1,2-dihydronaphthalene

Hathaway, BA; Nichols, DE; Nichols, MB; Yim, GKW. A new, potent, conformationally-restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene. J. Med. Chem., 1 Jan 1982, 25 (5), 535–538. 563 kB. doi:10.1021/jm00347a011

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

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

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

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

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

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

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

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

N-Methyl-2-aminoindane

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

4-MA
PMA
4-Methoxyamphetamine

IUPAC: 1-(4-Methoxyphenyl)propan-2-amine

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: NEGYEDYHPHMHGK-UHFFFAOYSA-N Properties: Essential amphetamine

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

PubChem CID: 31721; ChemSpider: 29417; Erowid: PMA; Wikipedia: PMA

Shulgin Index: #110 PMA; Table: 3 Page: 324 Row: 4

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

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

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

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

Błachut, D; Wojtasiewicz, K; Czarnocki, Z; Szukalski, B. The analytical profile of some 4-methylthioamphetamine (4-MTA) homologues. Forensic Sci. Int., 20 Nov 2009, 192 (1–3) 98–114. 683 kB. doi:10.1016/j.forsciint.2009.08.009

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

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

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

Nichols, DE; Lloyd, DH; Hoffman, AJ; Nichols, MB; Yim, GKW. Effects of certain hallucinogenic amphetamine analogues on the release of [3H]-serotonin from rat brain synaptosomes. J. Med. Chem., 1 Jan 1982, 25 (5), 530–535. 804 kB. doi:10.1021/jm00347a010

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

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

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

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB.

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Shulgin, AT. TMA, PMA, PMMA, and MDMA effects. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Mar 2003.

Shulgin, AT. PMA. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 20 Feb 2001.

Shulgin, AT. Making MDMA (II): “Ecstasy”, MDMA, & Safrole. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 1 May 2002.

Cimbura, G. PMA deaths in Ontario. Can. Med. Assoc. J., 8 Jun 1974, 110 (8), 1263–1267.

2-MA
OMA
2-Methoxyamphetamine

IUPAC: 1-(2-Methoxyphenyl)propan-2-amine

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

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

PubChem CID: 159755; ChemSpider: 140465

Shulgin Index: #74 2-MA; Table: 3 Page: 320 Row: 1

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

3-MA
MMA (3-MA)
3-Methoxyamphetamine

IUPAC: 1-(3-Methoxyphenyl)propan-2-amine

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

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

PubChem CID: 152234; ChemSpider: 134180; Wikipedia: 3-Methoxyamphetamine

Shulgin Index: #75 3-MA; Table: 3 Page: 321 Row: 26

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

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

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

Hordenine
4-Hydroxy-N,N-dimethylphenethylamine

IUPAC: 4-[2-(Dimethylamino)ethyl]phenol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: KUBCEEMXQZUPDQ-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 68313; ChemSpider: 61609; Wikipedia: Hordenine

Shulgin Index: #71 Hordenine; Table: 3 Page: 323 Row: 15

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

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochem., 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

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

4-Methylnorephedrine

IUPAC: 2-Amino-1-(4-methylphenyl)propan-1-ol

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

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

PubChem CID: 37044; ChemSpider: 33992

β-HO-N,N-Me-PEA

IUPAC: 2-(Dimethylamino)-1-phenylethanol

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

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

PubChem CID: 120846; ChemSpider: 107874

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 11

AMPH-OH

IUPAC: [(1-Phenylpropan-2-yl)amino]methanol

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

InChI=1S/C10H15NO/c1-9(11-8-12)7-10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3

PubChem CID: 54463712

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 22

N,N-Me-2-HPEA

IUPAC: 2-[2-(Dimethylamino)ethyl]phenol

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

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

PubChem CID: 23423072; ChemSpider: 10467022

Shulgin Index: See #71 Hordenine; Table: 3 Page: 319 Row: 24

2-HMA

IUPAC: 2-[2-(Methylamino)propyl]phenol

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

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

PubChem CID: 11405; ChemSpider: 10927

Shulgin Index: See #74 2-MA; Table: 3 Page: 319 Row: 27

N-Me-2-MPEA

IUPAC: 2-(2-Methoxyphenyl)-N-methylethanamine

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

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

PubChem CID: 13092505; ChemSpider: 10634978

Shulgin Index: See #100 2-MPEA; Table: 3 Page: 319 Row: 29

β-Me-2-MPEA

IUPAC: 2-(2-Methoxyphenyl)propan-1-amine

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

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

PubChem CID: 408060; ChemSpider: 361051

Shulgin Index: See #100 2-MPEA; Table: 3 Page: 319 Row: 31

N,N-Me-3-HPEA

IUPAC: 3-[2-(Dimethylamino)ethyl]phenol

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

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

PubChem CID: 3029884; ChemSpider: 2295140

Shulgin Index: See #71 Hordenine; Table: 3 Page: 321 Row: 4

N-Me-3-MPEA

IUPAC: 2-(3-Methoxyphenyl)-N-methylethanamine

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

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

PubChem CID: 118500; ChemSpider: 105913

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 12

β-Me-3-MPEA

IUPAC: 2-(3-Methoxyphenyl)propan-1-amine

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

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

PubChem CID: 202627; ChemSpider: 175454

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 16

Pholedrine

IUPAC: 4-[2-(Methylamino)propyl]phenol

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

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

PubChem CID: 4655; ChemSpider: 4494

Shulgin Index: See #109 PHA; Table: 3 Page: 323 Row: 23

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

α-Et-4-HPEA

IUPAC: 4-(2-Aminobutyl)phenol

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

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

PubChem CID: 43566042; ChemSpider: 28148634

Shulgin Index: See #110 PMA; Table: 3 Page: 323 Row: 29

N-Me-4-MPEA

IUPAC: 2-(4-Methoxyphenyl)-N-methylethanamine

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

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

PubChem CID: 104735; ChemSpider: 94550

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 323 Row: 33

β-Me-4-MPEA

IUPAC: 2-(4-Methoxyphenyl)propan-1-amine

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

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

PubChem CID: 202625; ChemSpider: 175452

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 323 Row: 36

4-EPEA

IUPAC: 2-(4-Ethoxyphenyl)ethanamine

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

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

PubChem CID: 143354; ChemSpider: 126469

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 324 Row: 19

2,3-HMeMPEA

IUPAC: 2-Methyl-6-[2-(methylamino)ethyl]phenol

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

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

ChemSpider: 27019897

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 14

2,3-HMeA

IUPAC: 2-(2-Aminopropyl)-6-methylphenol

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

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

PubChem CID: 14265622; ChemSpider: 26495759

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 16

2,4-MMPEA

IUPAC: 2-(2-Methoxy-4-methylphenyl)ethanamine

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

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

PubChem CID: 417604; ChemSpider: 369665

Shulgin Index: See #47 2,4-DMPEA; Table: 4 Page: 326 Row: 35

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

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

β-HO-3,4-MePEA

IUPAC: 2-Amino-1-(3,4-dimethylphenyl)ethanol

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

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

PubChem CID: 43752583; ChemSpider: 25642914

Shulgin Index: See #43 DMePEA; Table: 4 Page: 327 Row: 33

3,4-HMeA

IUPAC: 5-(2-Aminopropyl)-2-methylphenol

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

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

PubChem CID: 167995; ChemSpider: 146955

Shulgin Index: See #96 3,4-MMA; Table: 4 Page: 328 Row: 1