AM-2201

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Chemical compound

title: "AM-2201" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["naphthoylindoles", "organofluorides", "am-cannabinoids", "designer-drugs", "cb1-receptor-agonists", "cb2-receptor-agonists"] description: "Chemical compound" topic_path: "general/naphthoylindoles" source: "https://en.wikipedia.org/wiki/AM-2201" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 451565418 | IUPAC_name = 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone | image = AM-2201.svg | image_class = skin-invert-image | width = 180

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_BR = F2 | legal_BR_comment = | legal_CA = Schedule II | legal_DE = Anlage II | legal_UK = Class B | legal_US = Schedule I | legal_NZ = Temporary Class | legal_UN = P II | legal_UN_comment = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 335161-24-5 | ATC_prefix = | ATC_suffix = | PubChem = 53393997 | KEGG = C22771 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 24751884 | UNII_Ref = | UNII = TBJ0966F1O

| C=24 | H=22 | F=1 | N=1 | O=1 | smiles = O=C(C1=CN(CCCCCF)C2=C1C=CC=C2)C3=CC=CC4=C3C=CC=C4 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = ALQFAGFPQCBPED-UHFFFAOYSA-N

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. It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University.

Hazards

Convulsions have been reported including at doses as low as 10 mg.

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. 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. 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.

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.

Legal status

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

References

References

  1. Anvisa. (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. "Substance Details AM-2201".
  3. (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry.
  4. (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.
  5. ekaJ. (20 February 2011). "The Night I Killed My Friends". Erowid.org.
  6. "Cannabimimetic indole derivatives".
  7. (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.
  8. "Southern Association of Forensic Scientists".
  9. [https://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf Controlled Substances listed by the DEA]

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naphthoylindolesorganofluoridesam-cannabinoidsdesigner-drugscb1-receptor-agonistscb2-receptor-agonists