|Chemical and physical data|
|Molar mass||359.44 g/mol g·mol−1|
|3D model (JSmol)|
|(what is this?)|
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. It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University.
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.
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. 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. 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.
A forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.
- Wilkinson SM, Banister, Kassiou M (2015). “Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids”. Australian Journal of Chemistry. 68 (1): 4–8. doi:10.1071/CH14198.
- McQuade D, Hudson S, Dargan PI, Wood DM (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): 373–6. doi:10.1007/s00228-012-1379-2. PMID 22936123.
- ekaJ (20 February 2011). “The Night I Killed My Friends”. Erowid.org. Retrieved 11 June 2012.
- Synthetic Drug Control Act of 2011. H.R. 1254, 112th Congress, 1st Session (2011).
- WO patent 0128557, Makriyannis A, Deng H, “Cannabimimetic indole derivatives”, granted 2001-06-07
- Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M (August 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. 6 (8): 1445–58. doi:10.1021/acschemneuro.5b00107. PMID 25921407.
- Southern Association of Forensic Scientists