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Contents

   



(Top)
 


1 Hazards  





2 Pharmacology  



2.1  Pharmacokinetics  







3 Detection  





4 Legal status  





5 See also  





6 References  














AM-2201






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AM-2201
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • NZ: Temporary Class
  • UK: Class B
  • US: Schedule I
  • UN: Psychotropic Schedule II[2]
  • Identifiers
    • 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone

    CAS Number
    PubChem CID
    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 a recreational designer drug that acts as a potent but nonselective full agonist for the cannabinoid receptor.[3] It is part of the AM series of cannabinoids discovered by Alexandros MakriyannisatNortheastern University.

    Hazards[edit]

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

    Pharmacology[edit]

    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.[6] 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.[7] 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.[7]

    Pharmacokinetics[edit]

    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[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 a Schedule 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. Retrieved 2023-08-27.
  • ^ "Substance Details AM-2201". Retrieved 2024-01-22.
  • ^ 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.
  • ^ 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.
  • ^ ekaJ (20 February 2011). "The Night I Killed My Friends". Erowid.org. Retrieved 11 June 2012.
  • ^ WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  • ^ a b 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.
  • ^ "Southern Association of Forensic Scientists". Archived from the original on 2014-09-10. Retrieved 2013-07-16.
  • ^ Controlled Substances listed by the DEA

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=AM-2201&oldid=1197943329"

    Categories: 
    Naphthoylindoles
    Organofluorides
    AM cannabinoids
    Designer drugs
    CB1 receptor agonists
    CB2 receptor agonists
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    All articles with unsourced statements
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