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AM-2201

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
AM-2201
Legal status
Legal status
Identifiers
  • 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H22FNO
Molar mass359.444 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
 ☒NcheckY (what is this?)  (verify)

AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole) is arecreationaldesigner drug that acts as a potent but nonselectivefull agonist for thecannabinoid receptor.[3] It is part of theAM series of cannabinoids discovered byAlexandros Makriyannis atNortheastern University.

Hazards

[edit]

Convulsions have been reported[4] including at doses as low as 10 mg.[5]

Pharmacology

[edit]

AM-2201 is afull agonist forcannabinoid receptors. Affinities are: with aKi of 1.0 nM atCB1 and 2.6 nM atCB2.[6] The 4-methylfunctional analogMAM-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.[7] AM-2201 producesbradycardia and hypothermia in rats at doses of 0.3–3 mg/kg, comparable to the potency ofJWH-018 in rats, suggesting potent cannabinoid-like activity.[7]

Pharmacokinetics

[edit]
See also:JWH-018 § Pharmacokinetics

AM-2201metabolism differs only slightly from that ofJWH-018. AM-2201N-dealkylation produces fluoropentane instead ofpentane (or plainalkanes in general).[citation needed]

Detection

[edit]

A forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[8]

Legal status

[edit]

In the United States, AM-2201 is aSchedule I controlled substance.[9]

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-07-24)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27.
  2. ^"Substance Details AM-2201". Retrieved2024-01-22.
  3. ^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.
  4. ^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.
  5. ^ekaJ (20 February 2011)."The Night I Killed My Friends".Erowid.org. Retrieved11 June 2012.
  6. ^WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  7. ^abBanister 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.
  8. ^"Southern Association of Forensic Scientists". Archived fromthe original on 2014-09-10. Retrieved2013-07-16.
  9. ^Controlled Substances listed by the DEA
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