MAM-2201

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MAM-2201
MAM-2201 structure.png
Systematic (IUPAC) name
(1-(5-fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)-methanone
Clinical data
Legal status
  • Temporary Class Drug (NZ)
Identifiers
CAS Registry Number 1354631-24-5 YesY
PubChem CID: 66570720
ChemSpider 28289977
Chemical data
Formula C25H24FNO
Molecular mass 373.462 g/mol

MAM-2201 (4'-methyl-AM-2201, 5"-fluoro-JWH-122) is a drug that presumably acts as a potent agonist for the cannabinoid receptors. 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.[1][2][3] 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. MAM-2201 has been banned by being added to the temporary class drug schedule in New Zealand, effective from 13 July 2012.[4]

A study of MAM-2201 in rats showed that it causes neurofunctional disruptions.[5]

References[edit]

  1. ^ EMCDDA–Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
  2. ^ Moosmann, B. et al. (2012). "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–e22. doi:10.1016/j.forsciint.2011.12.010. PMID 22264627.   edit
  3. ^ Simolka, K. et al. (2012). "Analysis of synthetic cannabinoids in "spice-like" herbal highs: Snapshot of the German market in summer 2011". Analytical and Bioanalytical Chemistry 404 (1): 157–171. doi:10.1007/s00216-012-6122-4. PMID 22710567.   edit
  4. ^ Temporary Class Drug Notice, 5 July 2012. NZ Department of Internal Affairs.
  5. ^ Zaitsu, K; Hayashi, Y; Suzuki, K; Nakayama, H; Hattori, N; Takahara, R; Kusano, M; Tsuchihashi, H; Ishi, A (2015). "Metabolome disruption of the rat cerebrum induced by the acute toxic effects of the synthetic cannabinoid MAM-2201". Life Sciences. doi:10.1016/j.lfs.2015.05.013. PMID 26032255.