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 number 1354631-24-5 YesY
ATC code ?
PubChem CID 66570720
ChemSpider 28289977
Chemical data
Formula C25H24FNO 
Mol. 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]

Pharmacology[edit]

Nothing has been published on the pharmacology of MAM-2201, though it presumably has similar properties to the closely related AM-2201 and JWH-122, which are both full agonists and unselectively bind to CB1 and CB2 cannabinoid receptors with low nanomolar affinity.

Pharmacokinetics[edit]

The pharmacokinetics of MAM-2201 has not been studied, but its metabolism likely differs only slightly from that of JWH-018, with the main metabolic pathway being hydroxylation at various positions, followed by glucuronidation of the hydroxylated metabolites. N-dealkylation is also likely to occur, producing fluoroalkyl metabolites and ultimately 3-fluoropropanoic acid, though the odd-numbered alkyl chain of MAM-2201 would not be expected to produce fluoroacetate as a metabolite. Also metabolism of the related compound AM-694 has shown hydrolytic defluorination of the alkyl chain, meaning any fluoroalkyl metabolites formed are likely to be further metabolised themselves.[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. ^ Grigoryev, A.; Kavanagh, P.; Melnik, A. (2012). "The detection of the urinary metabolites of 1-(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (AM-694), a high affinity cannabimimetic, by gas chromatography - mass spectrometry". Drug Testing and Analysis 5 (2): 110–5. doi:10.1002/dta.1336. PMID 22522907.  edit