AM-2201

AM-2201
Legal status
Legal status
Identifiers
IUPAC name
  • 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 mass359.444 g·mol−1
3D model (JSmol)
SMILES
  • O=C(C1=CN(CCCCCF)C2=C1C=CC=C2)C3=CC=CC4=C3C=CC=C4
InChI
  • 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
 ☒NcheckY (what is this?)  (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]

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.[4] 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.[5] 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.[5]

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.[6]

In the United States, AM-2201 is a Schedule I controlled substance.[7]

See also

References

  1. ↑ 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.
  2. ↑ 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. S2CID 23136932.
  3. ↑ ekaJ (20 February 2011). "The Night I Killed My Friends". Erowid.org. Retrieved 11 June 2012.
  4. ↑ WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
  5. 1 2 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.
  6. ↑ "Southern Association of Forensic Scientists". Archived from the original on 2014-09-10. Retrieved 2013-07-16.
  7. ↑ Controlled Substances listed by the DEA
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