4-Me-EABP
4-Methyl-(ethylamino)butrophenone

IUPAC: 2-(Ethylamino)-1-(4-methylphenyl)butan-1-one

Formula: C13H19NO Molecular weight: 205.29606 g/mol InChI Key: ZTIPDEPKTDPNQE-UHFFFAOYSA-N

InChI=1S/C13H19NO/c1-4-12(14-5-2)13(15)11-8-6-10(3)7-9-11/h6-9,12,14H,4-5H2,1-3H3

ChemSpider: 26704721

4-Me-MCAT
4-MMC
Mephedrone
4-Methylmethcathinone

IUPAC: 2-(Methylamino)-1-(4-methylphenyl)propan-1-one

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

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

PubChem CID: 45266826; ChemSpider: 21485694; Drugs Forum: Mephedrone; Erowid: 4-Methylmethcathinone; Wikipedia: Mephedrone

Shulgin Index: See #92 METHCATH; Table: 3 Page: 323 Row: 2

Brandt, SD; Sumnall, HR; Measham, F; Cole, J. Analyses of second-generation ‘legal highs’ in the UK: Initial findings. Drug Test. Anal., 1 Aug 2010, 2 (8), 377–382. 317 kB. doi:10.1002/dta.155

Dargan, PI; Sedefov, R; Gallegos, A; Wood, DM. The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone). Drug Test. Anal., 1 Jul 2011, 3 (7–8), 454–463. 149 kB. doi:10.1002/dta.312

Morris, K. UK places generic ban on mephedrone drug family. Lancet, 17 Apr 2010, 375 (9723), 1333–1334. 52 kB. doi:10.1016/S0140-6736(10)60559-4

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

Camilleri, A; Johnston, MR; Brennan, M; Davis, S; Caldicott, DGE. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, α-phthalimidopropiophenone and N-ethylcathinone. Forensic Sci. Int., 1 Jan 2010, in press. 736 kB. doi:10.1016/j.forsciint.2009.12.048

Jankovics, P; Váradi, A; Tölgyesi, L; Lohner, S; Németh-Palotás, J; Kőszegi-Szalai, H. Identification and characterization of the new designer drug 4′-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 213–220. 899 kB. doi:10.1016/j.forsciint.2011.03.019

Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, P; O’Brien, J. The analysis of substituted cathinones. Part 1: Chemical analysis of 2-, 3-, and 4-methylmethcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 6–12. 1032 kB. doi:10.1016/j.forsciint.2011.04.020

McDermott, SD; Power, JD; Kavanagh, P; 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

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

Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005

Santali, EY; Cadogan, A; Daeid, NN; Savage, KA; Sutcliffe, OB. Synthesis, full chemical characterisation and development of validated methods for the quantification of (±)-4′-methylmethcathinone (mephedrone): a new “legal high”. J. Pharmaceut. Biomed. Anal., 10 Sep 2011, 56 (2), 246–255. 705 kB. doi:10.1016/j.jpba.2011.05.022

Khreit, OIG; Grant, MH; Zhang, T; Henderson, C; Watson, DG; Sutcliffe, OB. Elucidation of the Phase I and Phase II metabolic pathways of (±)-4′-methylmethcathinone (4-MMC) and (±)-4′-(trifluoromethyl)methcathinone (4-TFMMC) in rat liver hepatocytes using LC–MS and LC–MS2. J. Pharm. Biomed. Anal., 18 Jan 2013, 72, 177–185. 800 kB. doi:10.1016/j.jpba.2012.08.015

Wood, DM; Dargan, PI. Mephedrone (4-methylmethcathinone): What is new in our understanding of its use and toxicity. Prog. Neuro-Psychopharmacol. Biol. Psychiatry, . 251 kB. doi:10.1016/j.pnpbp.2012.04.020

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

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

Brunt, TM; Poortman, A; Niesink, RJM; Brink, W. Instability of the ecstasy market and a new kid on the block: mephedrone. J. Psychopharmacol., 1 Nov 2011, 25 (11), 1543–1547. 238 kB. doi:10.1177/0269881110378370

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

Maheux, CR; Copeland, CR; Pollard, MM. Characterization of three methcathinone analogs: 4-methylmethcathinone, methylone, and bk-MBDB. Microgram J., 1 Dec 2010, 7 (2), 43–49. 765 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.

Meyers-Riggs, B. AIRCR jumps the shark. countyourculture: rational exploration of the underground, 30 Dec 2010.

MABP
Buphedrone
α-(Methylamino)butyrophenone
Dibutylone

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

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

4-F-MABP
4-Fluoro-(methylamino)butyrophenone

IUPAC: 1-(4-Fluorophenyl)-2-(methylamino)butan-1-one

Formula: C11H14FNO Molecular weight: 195.2333632 g/mol InChI Key: NEZHKHMZNSFKGS-UHFFFAOYSA-N

InChI=1S/C11H14FNO/c1-3-10(13-2)11(14)8-4-6-9(12)7-5-8/h4-7,10,13H,3H2,1-2H3

ChemSpider: 26702901

MeO-B
4-Methoxybuphedrone

IUPAC: 1-(4-Methoxyphenyl)-2-(methylamino)butan-1-one

Formula: C12H17NO2 Molecular weight: 207.26888 g/mol InChI Key: XHYJOZXDHKBQQS-UHFFFAOYSA-N

InChI=1S/C12H17NO2/c1-4-11(13-2)12(14)9-5-7-10(15-3)8-6-9/h5-8,11,13H,4H2,1-3H3

ChemSpider: 26705218

MPBP
4′-Methyl-α-pyrrolidinobutanophenone

IUPAC: 1-(4-Methylphenyl)-2-(pyrrolidin-1-yl)butan-1-one

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

InChI=1S/C15H21NO/c1-3-14(16-10-4-5-11-16)15(17)13-8-6-12(2)7-9-13/h6-9,14H,3-5,10-11H2,1-2H3

PubChem CID: 129775; Wikipedia: 4'-Methyl-α-pyrrolidinobutiophenone

Westphal, F; Junge, T; Rösner, P; Fritschi, G; Kleinc, B; Girreser, U. Mass spectral and NMR spectral data of two new designer drugs with an α-aminophenone structure: 4′-Methyl-α-pyrrolidinohexanophenone and 4′-methyl-α-pyrrolidinobutyrophenone. Forensic Sci. Int., 1 Jan 2007, 169 (1), 32–42. 1465 kB. doi:10.1016/j.forsciint.2006.07.024

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

4-MePEA

IUPAC: 2-(4-Methylphenyl)ethanamine

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

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

PubChem CID: 76751; ChemSpider: 69207

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 322 Row: 36

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

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

p-Methylaminorex

IUPAC: 5-(4-Methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine

Formula: C10H12N2O Molecular weight: 176.21508 g/mol InChI Key: ZEQYKJRCFOFECD-UHFFFAOYSA-N

InChI=1S/C10H12N2O/c1-7-2-4-8(5-3-7)9-6-12-10(11)13-9/h2-5,9H,6H2,1H3,(H2,11,12)

PubChem CID: 550760; ChemSpider: 479130

Anon. Personal communication of unpublished research. 1 Jun 2012.

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

O-2477

IUPAC: 1-(4-Methylphenyl)-2-(pyrrolidin-1-ylmethyl)pentan-1-one

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

InChI=1S/C17H25NO/c1-3-6-16(13-18-11-4-5-12-18)17(19)15-9-7-14(2)8-10-15/h7-10,16H,3-6,11-13H2,1-2H3

PubChem CID: 11514441; ChemSpider: 9689231

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

O-2525

IUPAC: 1-(4-Methylphenyl)-3-(pyrrolidin-1-yl)pentan-1-one

Formula: C16H23NO Molecular weight: 245.35992 g/mol InChI Key: CCCKABNBMAAFTD-UHFFFAOYSA-N

InChI=1S/C16H23NO/c1-3-15(17-10-4-5-11-17)12-16(18)14-8-6-13(2)7-9-14/h6-9,15H,3-5,10-12H2,1-2H3

PubChem CID: 11580039; ChemSpider: 9754805

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

3,4-DMMC
3,4-Dimethylmethcathinone

IUPAC: 1-(3,4-Dimethylphenyl)-2-(methylamino)propan-1-one

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

InChI=1S/C12H17NO/c1-8-5-6-11(7-9(8)2)12(14)10(3)13-4/h5-7,10,13H,1-4H3

PubChem CID: 52988261; ChemSpider: 25630192

4-MEC
4-Methylethcathinone

IUPAC: 2-(Ethylamino)-1-(4-methylphenyl)propan-1-one

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

InChI=1S/C12H17NO/c1-4-13-10(3)12(14)11-7-5-9(2)6-8-11/h5-8,10,13H,4H2,1-3H3

PubChem CID: 52988259; ChemSpider: 25630091; Erowid: 4-Methylethcathinone (4-MEC); Wikipedia: 4-Methylethcathinone

Brandt, SD; Sumnall, HR; Measham, F; Cole, J. Analyses of second-generation ‘legal highs’ in the UK: Initial findings. Drug Test. Anal., 1 Aug 2010, 2 (8), 377–382. 317 kB. doi:10.1002/dta.155

Jankovics, P; Váradi, A; Tölgyesi, L; Lohner, S; Németh-Palotás, J; Kőszegi-Szalai, H. Identification and characterization of the new designer drug 4′-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 213–220. 899 kB. doi:10.1016/j.forsciint.2011.03.019

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

4-EMC
4-Ethylmethcathinone

IUPAC: 1-(4-Ethylphenyl)-2-(methylamino)propan-1-one

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

InChI=1S/C12H17NO/c1-4-10-5-7-11(8-6-10)12(14)9(2)13-3/h5-9,13H,4H2,1-3H3

ChemSpider: 25630253

7,6-MMAT
2-Amino-7-methoxy-6-methyltetralin

IUPAC: 7-Methoxy-6-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C12H17NO/c1-8-5-9-3-4-11(13)6-10(9)7-12(8)14-2/h5,7,11H,3-4,6,13H2,1-2H3

PubChem CID: 36245; ChemSpider: 33329

Shulgin Index: See #105 PAT; Table: 4 Page: 337 Row: 6, See #96 3,4-MMA; Table: 5 Page: 342 Row: 7

NEB
N-Ethylbuphedrone

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

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

InChI=1S/C12H17NO/c1-3-11(13-4-2)12(14)10-8-6-5-7-9-10/h5-9,11,13H,3-4H2,1-2H3

PubChem CID: 20326296

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

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

PAP

IUPAC: 1-Phenyl-2-(propylamino)propan-1-one

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

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

PubChem CID: 45049; ChemSpider: 40983

Shulgin Index: See #40 DMAP; Table: 2 Page: 319 Row: 1

i-PAP

IUPAC: 1-Phenyl-2-(propan-2-ylamino)propan-1-one

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

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

PubChem CID: 458522; ChemSpider: 403507

Shulgin Index: See #40 DMAP; Table: 2 Page: 319 Row: 2

IBF5MAP

IUPAC: 1-(1,3-Dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amine

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 327 Row: 31

MMAT

IUPAC: 7-(Dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-ol

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

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

PubChem CID: 15629515; ChemSpider: 14106459

EHAT

IUPAC: 7-(Ethylamino)-5,6,7,8-tetrahydronaphthalen-1-ol

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

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

PubChem CID: 21689038; ChemSpider: 14106470

Shulgin Index: See #105 PAT; Table: 4 Page: 337 Row: 7

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