AM-2201

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
AM-2201
AM-2201.svg
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
Molecular 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

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.[original research?] 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).[citation needed]

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

  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. Acute Kidney Injury Associated with Synthetic Cannabinoid Use, Multiple States, 2012. CDC morbitidy and mortality weekly report 2012.
  6. Forbes Synthetic Marijuana May Cause Psychosis, Brain and Kidney Damage. Forbes report, Synthetic Marijuana Linked to Psychosis, Brain, and Kidney Damage. 2013
  7. PubMed Report, 2015. PubMed Psychosis and severe rhabdomyolysis associated with synthetic cannabinoid use, 2015
  8. Bowling Green Daily News Report 2011. Bowling Green Daily News Report, 2011
  9. Phys.org Report 2013. Phys.org Website, 2013
  10. WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  11. 11.0 11.1 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. 
  12. Southern Association of Forensic Scientists