MAM-2201 explained

MAM-2201 (4'-methyl-AM-2201, 5"-fluoro-JWH-122) is a drug that presumably acts as a potent agonist for the cannabinoid receptors.^{[1] [2]} It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in the Netherlands and Germany in June 2011 as an ingredient in synthetic cannabis smoking blends.^{[3] [4] [5]} Like RCS-4 and AB-001, MAM-2201 thus appears to be a novel compound invented by "research chemical" suppliers specifically for grey-market recreational use. Structurally, MAM-2201 is a hybrid of two known cannabinoid compounds JWH-122 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.

A study of MAM-2201 in rats showed that it causes neurofunctional disruptions.^[6] A later study demonstrated that MAM-2201 bound to and activated human CB1 and CB2 cannabinoid receptors and substituted for THC in THC drug discrimination in mice.^[7]

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as MAM-2201 are Schedule I Controlled Substances.

MAM-2201 has been banned by being added to the temporary class drug schedule in New Zealand, effective from 13 July 2012.^[8]

As of October 2015 MAM-2201 is a controlled substance in China.^[9]

See also

• 5F-JWH-398
• EAM-2201
• NM-2201
• THJ-2201
• Structural scheduling of synthetic cannabinoids

Notes and References

1. Zaitsu K, Nakayama H, Yamanaka M, Hisatsune K, Taki K, Asano T, Kamata T, Katagai M, Hayashi Y, Kusano M, Tsuchihashi H, Ishii A . 6 . High-resolution mass spectrometric determination of the synthetic cannabinoids MAM-2201, AM-2201, AM-2232, and their metabolites in postmortem plasma and urine by LC/Q-TOFMS . International Journal of Legal Medicine . 129 . 6 . 1233–45 . November 2015 . 26349566 . 10.1007/s00414-015-1257-4 . 24905067 .
2. Kim JH, Kong TY, Moon JY, Choi KH, Cho YY, Kang HC, Lee JY, Lee HS . 6 . Targeted and non-targeted metabolite identification of MAM-2201 in human, mouse, and rat hepatocytes . Drug Testing and Analysis . 10 . 8 . 1328–1335 . April 2018 . 29608249 . 10.1002/dta.2389 .
3. http://www.emcdda.europa.eu/publications/implementation-reports/2011 EMCDDA–Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
4. Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V . Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC-MS, NMR analysis and a flash chromatography system . Forensic Science International . 220 . 1–3 . e17-22 . July 2012 . 22264627 . 10.1016/j.forsciint.2011.12.010 .
5. Simolka K, Lindigkeit R, Schiebel HM, Papke U, Ernst L, Beuerle T . Analysis of synthetic cannabinoids in "spice-like" herbal highs: snapshot of the German market in summer 2011 . Analytical and Bioanalytical Chemistry . 404 . 1 . 157–71 . July 2012 . 22710567 . 10.1007/s00216-012-6122-4 . 24068469 .
6. Zaitsu K, Hayashi Y, Suzuki K, Nakayama H, Hattori N, Takahara R, Kusano M, Tsuchihashi H, Ishii A . 6 . Metabolome disruption of the rat cerebrum induced by the acute toxic effects of the synthetic cannabinoid MAM-2201 . Life Sciences . 137 . 49–55 . September 2015 . 26032255 . 10.1016/j.lfs.2015.05.013 .
7. Marusich JA, Wiley JL, Lefever TW, Patel PR, Thomas BF . Finding order in chemical chaos - Continuing characterization of synthetic cannabinoid receptor agonists . Neuropharmacology . 134 . Pt A . 73–81 . May 2018 . 29113898 . 5934329 . 10.1016/j.neuropharm.2017.10.041 .
8. http://www.dia.govt.nz/MSOS118/On-Line/NZGazette.nsf/6cee7698a9bbc7cfcc256d510059ed0b/1800482ea20e00f8cc257a32005ae9f8!OpenDocument Temporary Class Drug Notice, 5 July 2012. NZ Department of Internal Affairs.
9. Web site: 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 . China Food and Drug Administration . 27 September 2015 . Chinese . 1 October 2015.