AM-2201

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AM-2201
AM-2201 structure.png
Systematic (IUPAC) name
1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone
Clinical data
Legal status
Identifiers
CAS Number 335161-24-5 YesY
ChemSpider 24751884 YesY
Chemical data
Formula C24H22FNO
Molar mass 359.44 g/mol
  (verify)

AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole) is a recreational designer drug that acts as a potent but nonselective full agonist for the cannabinoid receptor.[1] It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University.

Hazards[edit]

Convulsions have been reported[2] including at doses as low as 10 mg.[3]

Recreational use of AM-2201 in the United States has led to it being specifically listed in a proposed 2011 amendment to the Controlled Substances Act, aiming to add a number of synthetic drugs into Schedule I.[4] As of November 2011, there have been no reports of death associated with the drug.[needs update] The acute toxicity and long term side effects associated with the use of AM-2201 are unknown.

Pharmacology[edit]

AM-2201 is a full agonist for cannabinoid receptors. Affinities are: with a Ki of 1.0 nM at CB1 and 2.6 nM at CB2.[5] The 4-methyl functional analog MAM-2201 probably has similar affinities.[original research?] AM-2201 has an EC50 of 38 nM for human CB1 receptors, and 58 nM for human CB2 receptors.[6] AM-2201 produces bradycardia and hypothermia in rats at doses of 0.3-3 mg/kg, comparable to the potency of JWH-018 in rats, suggesting potent cannabinoid-like activity.[6]

Pharmacokinetics[edit]

AM-2201 metabolism differs only slightly from that of JWH-018. AM-2201 N-dealkylation produces fluoropentane instead of pentane (or plain alkanes in general).[citation needed]

Detection[edit]

A forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[7]

See also[edit]

References[edit]

  1. ^ Wilkinson, S. M.; Banister, S. D.; Kassiou, M. (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry 68: 4. doi:10.1071/CH14198. 
  2. ^ David McQuade, Simon Hudson, Paul I. Dargan, David M. Wood (March 2013). "First European case of convulsions related to analytically confirmed use of the synthetic cannabinoid receptor agonist AM-2201". European Journal of Clinical Pharmacology 69 (3): 373–376. doi:10.1007/s00228-012-1379-2. 
  3. ^ ekaJ (20 February 2011). "The Night I Killed My Friends". Erowid.org. Retrieved 11 June 2012. 
  4. ^ Synthetic Drug Control Act of 2011. H.R. 1254, 112th Congress, 1st Session (2011).
  5. ^ WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  6. ^ a b Banister, S. D.; Stuart, J.; Kevin, R. C.; Edington, A.; Longworth, M.; Wilkinson, S. M.; Beinat, C.; Buchanan, A. S.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (2015). "Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135". ACS Chemical Neuroscience: 150508124201002. doi:10.1021/acschemneuro.5b00107. 
  7. ^ Southern Association of Forensic Scientists