|This article needs additional citations for verification. (September 2014)|
||This article possibly contains original research. (September 2014)|
|Systematic (IUPAC) name|
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|Molecular mass||359.44 g/mol|
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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.
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. Convulsions have been reported including at doses as low as 10 mg. 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. 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.
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.
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A forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.
- 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.
- 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.
- 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, 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.
- Southern Association of Forensic Scientists