AM-2201
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| Identifiers | |
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| CAS Number |
335161-24-5  |
| PubChem (CID) | 53393997 |
| ChemSpider |
24751884 |
| UNII | TBJ0966F1O |
| Chemical and physical data | |
| Formula | C24H22FNO |
| Molar mass | 359.44 g/mol |
| 3D model (Jmol) | Interactive image |
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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.[1] It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University.
Hazards
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] The acute toxicity and long term side effects associated with the use of AM-2201 are acute kidney failure, brain damage, strokes, convulsions, seizures, rhabdomyolysis, and death.[5][6][7][8][9]
Pharmacology
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.[10] The 4-methyl functional analog MAM-2201 probably has similar affinities. AM-2201 has an EC50 of 38 nM for human CB1 receptors, and 58 nM for human CB2 receptors.[11] 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.[11]
Pharmacokinetics
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).
Detection
A forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[12]
See also
References
- ↑ Wilkinson, S. M.; Banister, S. D.; Kassiou, M. (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry. 68 (1): 4–8. 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. 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).
- ↑ Acute Kidney Injury Associated with Synthetic Cannabinoid Use, Multiple States, 2012. CDC morbitidy and mortality weekly report 2012.
- ↑ Forbes Synthetic Marijuana May Cause Psychosis, Brain and Kidney Damage. Forbes report, Synthetic Marijuana Linked to Psychosis, Brain, and Kidney Damage. 2013
- ↑ Dante Durand; Leticia L. Delgado; Dhizarah Matus de la Parra-Pellot; Diana Nichols-Vinueza (January 2015). "Psychosis and Severe Rhabdomyolysis Associated with Synthetic Cannabinoid Use". Clinical Schizophrenia & Related Psychoses. 8 (4): 205–208. doi:10.3371/CSRP.DUDE.031513. PMID 23518784.
- ↑ Bowling Green Daily News Report 2011. Bowling Green Daily News Report, 2011
- ↑ Phys.org Report 2013. Phys.org Website, 2013
- ↑ WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
- 1 2 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. (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): 1445–1458. doi:10.1021/acschemneuro.5b00107. PMID 25921407.
- ↑ Southern Association of Forensic Scientists