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4-Me-MABP; 4-Methylbuphedrone
2362
Variant: N α R4 skeleton isomers all
Analogues: 1 1 3 9 16 30

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

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

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

ChemSpider: 26702147

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

One N analogue:
2370
Analogue 1: Substituting Ethyl for Methyl at N

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

One α analogue:
2018
Analogue 1: Substituting Methyl for Ethyl at α

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

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

Spiller, HA; Ryan, ML; Weston, RG; Jansen, J. Clinical experience with and analytical confirmation of “bath salts” and “legal highs” (synthetic cathinones) in the United States. Clin. Toxicol., 1 Jul 2011, 49 (6), 499–505. 130 kB. doi:10.3109/15563650.2011.590812

Anon. Report on the risk assessment of mephedrone, European Monitoring Centre for Drugs and Drug Addiction, May 2011.

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

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

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

Westphal, F; Junge, T; Rösner, P; Girreser, U; Fritsch, R. Massenspektrometrische, infrarotspektroskopische und NMR-spekstroskopische Daten von Mephedron, Butylon und Methylon sowie einigen ihrer Derivate. Toxichem Krimtech, 2010, 77 (2), 95–116. 380 kB.

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

Kanu, AB; Brandt, SD; Williams, MD; Zhang, N; Hill, HH. Analysis of psychoactive cathinones and tryptamines by electrospray ionization atmospheric pressure ion mobility time-of-flight mass spectrometry. Anal. Chem., 17 Sep 2013, 85 (18), 8535–8542. 1636 kB. doi:10.1021/ac401951a

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

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

Gregg, RA; Rawls, SM. Behavioral pharmacology of designer cathinones: A review of the preclinical literature. Life Sci., 27 Feb 2014, 97 (1), 27–30. 249 kB. doi:10.1016/j.lfs.2013.10.033

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

German, CL; Fleckenstein, AE; Hanson, GR. Bath salts and synthetic cathinones: An emerging designer drug phenomenon. Life Sci., 27 Feb 2014, 97 (1), 2–8. 390 kB. doi:10.1016/j.lfs.2013.07.023

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

Iversen, L; Gibbons, S; Treble, R; Setola, V; Huang, X; Roth, BL. Neurochemical profiles of some novel psychoactive substances. Eur. J. Pharmacol., 30 Jan 2013, 700 (1–3), 147–151. 490 kB. doi:10.1016/j.ejphar.2012.12.006

Prosser, JM; Nelson, LS. The toxicology of bath salts: a review of synthetic cathinones. J. Med. Toxicol., 1 Nov 2011, 8 (1), 33–22. 267 kB. doi:10.1007/s13181-011-0193-z

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

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

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.

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

Iversen, LL. 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.

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

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

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

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. Pharm. Biomed. Anal., 10 Sep 2011, 56 (2), 246–255. 705 kB. doi:10.1016/j.jpba.2011.05.022

Brandt, SD; Sumnall, HR; Measham, F; Cole, JC. 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

Wood, DM; Dargan, PI. Mephedrone (4-methylmethcathinone): What is new in our understanding of its use and toxicity. Prog. Neuro-Psychopharmacol. Biol. Psychiatry, 3 Dec 2012. 251 kB. doi:10.1016/j.pnpbp.2012.04.020

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

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

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

Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, PV; 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

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

Sanchez, MJSB. Sur un homologue de l’éphédrine. Bull. Soc. Chim. Fr., 1929, 45, 284–286. 600 kB.

Three R4 analogues:
2340
Analogue 1: Removing Methyl at R4

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

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

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

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

2366
Analogue 2: Substituting Fluoro for Methyl at R4

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

363
Analogue 3: Substituting Methoxy for Methyl at R4

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

Nine skeleton analogues:
2118
Analogue 1: With 2-Cyclic-amine-1-phenylethanone skeleton

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

6236
Analogue 2: With 2-Phenylethan-1-amine skeleton

4-MePEA

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

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

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

563
Analogue 3: With Phenyl-cyclic-amine skeleton

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

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

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

1422
Analogue 4: With 3-Cyclic-amine-1-phenylpropanone skeleton

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

1424
Analogue 5: With 3-Cyclic-amine-1-phenylpropanone skeleton

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

1478
Analogue 6: With 2-Phenylcyclopropan-1-amine skeleton

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

2525
Analogue 7: With Phenylacetaldehyde skeleton

Isomephedrone

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

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

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

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

1029
Analogue 8: With Phenyl-cyclic-amine skeleton

4-Methylphendimetrazine

IUPAC: 3,4-Dimethyl-2-(4-methylphenyl)morpholine

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

InChI=1S/C13H19NO/c1-10-4-6-12(7-5-10)13-11(2)14(3)8-9-15-13/h4-7,11,13H,8-9H2,1-3H3

538
Analogue 9: With Phenyl-cyclic-amine skeleton

4,4′-DMAR
p,4-Dimethylaminorex

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

Brandt, SD; Baumann, MH; Partilla, JS; Kavanagh, PV; Power, JD; Talbot, B; Twamley, B; Mahony, O; O’Brien, J; Elliott, SP; Archer, RP; Patrick, J; Singh, K; Dempster, NM; Cosbey, SH. Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4′-DMAR, or ‘Serotoni’). Drug Test. Anal., 2014. 1068 kB. doi:10.1002/dta.1668

16 isomers:
2360
Isomer 1

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

Casale, JF; Hays, PA. Differentiation of 3,4-dimethylmethcathinone (3,4-DMMC) from its dimethyl aryl-positional isomers. Microgram J., 1 Jan 2012, 9 (2), 75–83. 1330 kB.

2372
Isomer 2

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, JC. 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

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

Kanu, AB; Brandt, SD; Williams, MD; Zhang, N; Hill, HH. Analysis of psychoactive cathinones and tryptamines by electrospray ionization atmospheric pressure ion mobility time-of-flight mass spectrometry. Anal. Chem., 17 Sep 2013, 85 (18), 8535–8542. 1636 kB. doi:10.1021/ac401951a

Gil, D; Adamowicz, P; Skulska, A; Tokarczyk, B; Stanaszek, R. Analysis of 4-MEC in biological and non-biological material—Three case reports. Forensic Sci. Int., 10 May 2013, 228 (1–3), e11–e15. 554 kB. doi:10.1016/j.forsciint.2013.03.011

Iversen, L; Gibbons, S; Treble, R; Setola, V; Huang, X; Roth, BL. Neurochemical profiles of some novel psychoactive substances. Eur. J. Pharmacol., 30 Jan 2013, 700 (1–3), 147–151. 490 kB. doi:10.1016/j.ejphar.2012.12.006

2373
Isomer 3

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

416
Isomer 4

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

2430
Isomer 5

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

2434
Isomer 6

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

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

6051
Isomer 7

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

6052
Isomer 8

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

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

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

6481
Isomer 9

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

6956
Isomer 10

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

6957
Isomer 11

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

1235
Isomer 12

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

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

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

2527
Isomer 13

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

1428
Isomer 14

6-MAPDB

IUPAC: 1-(2,3-Dihydro-1-benzofuran-6-yl)-N-methylpropan-2-amine

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

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

Wikipedia: 6-MAPDB

1429
Isomer 15

5-MAPDB

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

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

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

Wikipedia: 5-MAPDB

2576
Isomer 16

EMC
N-Ethylmethcathinone

IUPAC: 2-[Ethyl(methyl)amino]-1-phenylpropan-1-one

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

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

Show all 30 analogues and isomers Show only the one N analogues Show only the one α analogues Show only the three R4 analogues Show only the nine skeleton analogues
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