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AM-2201

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AM-2201
Legal status
Legal status
Identifiers
  • 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H22FNO
Molar mass359.44 g/mol g·mol−1
3D model (JSmol)
  • O=C(C1=CN(CCCCCF)C2=C1C=CC=C2)C3=CC=CC4=C3C=CC=C4
  • InChI=1S/C24H22FNO/c25-15-6-1-7-16-26-17-22(20-12-4-5-14-23(20)26)24(27)21-13-8-10-18-9-2-3-11-19(18)21/h2-5,8-14,17H,1,6-7,15-16H2 checkY
  • Key:ALQFAGFPQCBPED-UHFFFAOYSA-N checkY
  (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

See also: JWH-018 § 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 (1): 4–8. 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. PMID 22936123.
  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. ^ 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.
  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. ^ a b 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.
  12. ^ Southern Association of Forensic Scientists
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