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
ATC code ?
ChemSpider 24751884 YesY
Chemical data
Formula C24H22FNO 
Mol. mass 359.44 g/mol
 YesY (what is this?)  (verify)

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

Hazards[edit]

AM-2201 is widely regarded by recreational users of synthetic cannabinoids as one of the most potent and possibly the most potent substance available in this class of drugs.[citation needed] As the dosage is much smaller than other synthetic cannabinoids, accidental overdose becomes more likely. There have been anecdotal reports of individuals experiencing panic attacks and vomiting at doses as small as 2 mg.[citation needed] Convulsions have been reported[1] including at doses as low as 10 mg.[2] Caution should be taken if using this substance as it is active at doses as small as 500 µg, has a very steep dose-response curve, and tolerance builds up very quickly to the effects.

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.[3] 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 1.0nM at CB1 and 2.6nM at CB2.[4] The 4-methyl functional analog MAM-2201 probably has similar affinities.

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.[5]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ ekaJ (20 February 2011). "The Night I Killed My Friends". Erowid.org. Retrieved 11 June 2012. 
  3. ^ Synthetic Drug Control Act of 2011. H.R. 1254, 112th Congress, 1st Session (2011).
  4. ^ WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  5. ^ Southern Association of Forensic Scientists