Exploring Mephedrone. To explore a different substance…

IUPAC name:
ID: 2018 · Formula: C11H15NO · Molecular weight: 177.243
InChI: InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3
InChI Key: YELGFTGWJGBAQU-UHFFFAOYSA-NThis stereoisomerAny stereoisomer

Archer, R. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1.4 MB. https://doi.org/10.1016/j.forsciint.2008.11.013

Camilleri, A; Johnston, MR; Brennan, M; Davis, S; Caldicott, DG. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, α-phthalimidopropiophenone and N-ethylcathinone. Forensic Sci. Int., 15 Apr 2010, 197 (1), 59-66. 736 kB. https://doi.org/10.1016/j.forsciint.2009.12.048

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. 286 kB.

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. https://doi.org/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. https://doi.org/10.1038/npp.2011.304

Meyers-Riggs, B. AIRCR jumps the shark. countyourculture, 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. https://doi.org/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. Analysis, 1 Aug 2010, 2 (8), 377–382. 317 kB. https://doi.org/10.1002/dta.155

Jankovics, P; Váradi, A; Tõlgyesi, 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. https://doi.org/10.1016/j.forsciint.2011.03.019

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. 1.0 MB. https://doi.org/10.1016/j.forsciint.2011.04.020

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. https://doi.org/10.1016/j.forsciint.2012.02.005

Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3), 182-188. 1.4 MB. https://doi.org/10.1016/j.forsciint.2011.08.005

Brunt, TM; Poortman, A; Niesink, RJM; van den 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. https://doi.org/10.1177/0269881110378370

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

Wood, DM; Dargan, PI. Mephedrone (4-methylmethcathinone): What is new in our understanding of its use and toxicity. Prog. Neuro-Psychopharmacol. Biol. Psych., 3 Dec 2012, 39 (2), 227-233. 251 kB. https://doi.org/10.1016/j.pnpbp.2012.04.020

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.

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. 1.1 MB. https://doi.org/10.1016/j.forsciint.2011.06.030

Khreit, OI; 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. https://doi.org/10.1016/j.jpba.2012.08.015

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. https://doi.org/10.1016/j.trac.2011.09.009

Morris, K. UK places generic ban on mephedrone drug family. Lancet, 17 Apr 2010, 375 (9723), 1333–1334. 52 kB. https://doi.org/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. https://doi.org/10.3109/15563650.2011.590812

Anon. Report on the risk assessment of mephedrone, European Monitoring Centre for Drugs and Drug Addiction, May 2011. 2.2 MB.

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. Analysis, 1 May 2012, 4 (5), 342–354. 538 kB. https://doi.org/10.1002/dta.358

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’. Drug Test. Analysis, 1 Jun 2013, 5 (6), 420–429. 1.3 MB. https://doi.org/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. 1.6 MB. https://doi.org/10.1021/ac401951a

Cameron, K; Kolanos, R; Vekariya, R; De Felice, L; 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. https://doi.org/10.1007/s00213-013-2967-2

Westphal, F; Junge, T; Rõsner, 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.

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. 2.2 MB. https://doi.org/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. https://doi.org/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. https://doi.org/10.1016/j.lfs.2013.10.033

De Felice, LJ; Glennon, RA; Negus, SS. Synthetic cathinones: Chemical phylogeny, physiology, and neuropharmacology. Life Sci., 27 Feb 2014, 97 (1), 20–26. 697 kB. https://doi.org/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. https://doi.org/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. https://doi.org/10.1016/j.lfs.2013.07.015

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. https://doi.org/10.1007/s13181-011-0193-z

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. https://doi.org/10.1016/j.ejphar.2012.12.006

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

McElrath, K; O’Neill, C. Experiences with mephedrone pre- and post-legislative controls: Perceptions of safety and sources of supply. Int. J. Drug Policy, 1 Mar 2011, 22 (2), 120-127. 180 kB. https://doi.org/10.1016/j.drugpo.2010.11.001

Power, JD; Kavanagh, P; McLaughlin, G; O'Brien, J; Talbot, B; Barry, M; Twamley, B; Dowling, G; Brandt, SD. Identification and characterization of an imidazolium by-product formed during the synthesis of 4-methylmethcathinone (mephedrone): Identification and characterization of a mephedrone synthesis imputity. Drug Test. Analysis, 1 Oct 2015, 7 (10), 894-902. 1.3 MB. https://doi.org/10.1002/dta.1789

Baumann, MH; Partilla, JS; Lehner, KR; Thorndike, EB; Hoffman, AF; Holy, M; Rothman, RB; Goldberg, SR; Lupica, CR; Sitte, HH; Brandt, SD; Tella, SR; Cozzi, NV; Schindler, CW. Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive ‘bath salts’ products. Neuropsychopharmacology, 1 Mar 2013, 38 (4), 552-562. 1.4 MB. https://doi.org/10.1038/npp.2012.204

Kapitány-Fövény, M; Kertész, M; Winstock, A; Deluca, P; Corazza, O; Farkas, J; Zacher, G; Urbán, R; Demetrovics, Z. Substitutional potential of mephedrone: an analysis of the subjective effects. Hum. Psychopharmacol. Clin. Exp., 1 Jul 2013, 28 (4), 308–316. 141 kB. https://doi.org/10.1002/hup.2297

Bonano, JS; Glennon, RA; Felice, LJ; Banks, ML; Negus, SS. Abuse-related and abuse-limiting effects of methcathinone and the synthetic “bath salts” cathinone analogs methylenedioxypyrovalerone (MDPV), methylone and mephedrone on intracranial self-stimulation in rats. Psychopharmacology, 1 Jan 2014, 231 (1), 199-207. 285 kB. https://doi.org/10.1007/s00213-013-3223-5

Glennon, RA. Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention. Advances in Pharmacology, 2014, 69, 581–620. 564 kB. https://doi.org/10.1016/B978-0-12-420118-7.00015-9

Ogino, M; Naiki, T; Orui, H; Kosone, K; Yamazaki, M. Study of method for identifying phenethylamine drugs. JCCL, , 50, 63-82. 627 kB. Retrieved from http://www.customs.go.jp/ccl_search/e_info_search/drugs/r_50_08_e.pdf

Anon. New drugs in Europe, 2015, European Monitoring Centre for Drugs and Drug Addiction, 1 May 2016. 1.0 MB.

Luethi, D; Kolaczynska, KE; Docci, L; Krähenbühl, S; Hoener, MC; Liechti, ME. Pharmacological profile of mephedrone analogs and related new psychoactive substances. Neuropharmacology, 26 Jul 2017, n/a. 2.6 MB. https://doi.org/10.1016/j.neuropharm.2017.07.026 #4-MMC

Anon. New drugs in Europe, 2014, European Monitoring Centre for Drugs and Drug Addiction, 1 Jul 2015. 879 kB.

Anon. New drugs in Europe, 2013, European Monitoring Centre for Drugs and Drug Addiction, 1 Jul 2014. 311 kB.

Anon. New drugs in Europe, 2011, European Monitoring Centre for Drugs and Drug Addiction, 1 Apr 2012. 401 kB.

Anon. New drugs in Europe, 2010, European Monitoring Centre for Drugs and Drug Addiction, 1 May 2011. 700 kB.

McLaughlin, G; Morris, N; Kavanagh, PV; Power, JD; Dowling, G; Twamley, B; O’Brien, J; Talbot, B; Walther, D; Partilla, JS; Baumann, MH; Brandt, SD. Synthesis, characterization and monoamine transporter activity of the new psychoactive substance mexedrone and its N-methoxy positional isomer, N-methoxymephedrone. Drug Test. Analysis, 1 Jan 2016, 9 (3), 358-368. 1.0 MB. https://doi.org/10.1002/dta.2053

Gwak, S; Arroyo-Mora, LE; Almirall, JR. Qualitative analysis of seized synthetic cannabinoids and synthetic cathinones by gas chromatography triple quadrupole tandem mass spectrometry. Drug Test. Analysis, 1 Feb 2015, 7 (2), 121-130. 1.1 MB. https://doi.org/10.1002/dta.1667 #2

Bonano, JS; Banks, ML; Kolanos, R; Sakloth, F; Barnier, ML; Glennon, RA; Cozzi, NV; Partilla, JS; Baumann, MH; Negus, SS. Quantitative structure-activity relationship analysis of the pharmacology of para-substituted methcathinone analogues: QSAR of para-substituted methcathinone analogues. Br. J. Pharmacol., 2015, 172 (10), 2433-2444. 985 kB. https://doi.org/10.1111/bph.13030

Leffler, AM; Smith, PB; de Armas, A; Dorman, FL. The analytical investigation of synthetic street drugs containing cathinone analogs. Forensic Sci. Int., 1 Jan 2014, 234, 50-56. 973 kB. https://doi.org/10.1016/j.forsciint.2013.08.021

Meyer, MR; Wilhelm, J; Peters, FT; Maurer, HH. β-Keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry. Anal. Bioanal. Chem., 1 Jun 2010, 397 (3), 1225–1233. 451 kB. https://doi.org/10.1007/s00216-010-3636-5

Collins, M. Some new psychoactive substances: Precursor chemical and synthesis-driver end-products. Drug Test. Analysis, 1 Jul 2001, 3 (7–8), 404–416. 178 kB. https://doi.org/10.1002/dta.315

EAP · Ethcathinone
DMAP · Dimethylcathinone
MABP · Buphedrone
26 May 2018 · Creative Commons BY-NC-SA ·