AM-2201

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 Makriyannis at Northeastern University.

AM-2201

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] 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
IUPAC name 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone
CAS Number	335161-24-5 Y
PubChem CID	53393997
ChemSpider	24751884 Y
UNII	TBJ0966F1O
KEGG	C22771
CompTox Dashboard (EPA)	DTXSID50187158
Chemical and physical data
Formula	C24H22FNO
Molar mass	359.444 g·mol−1
3D model (JSmol)	Interactive image
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 Y Key:ALQFAGFPQCBPED-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Hazards

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

Pharmacology

AM-2201 is a full agonist for cannabinoid receptors. Affinities are: with a K_i 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

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.^[8]

Legal status

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

See also

• AM-694
• AM-1235
• AM-2232
• AM-2233
• JWH-018
• SDB-005
• THJ-018
• THJ-2201
• MEPIRAPIM
• NM-2201

References

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.
2. "Substance Details AM-2201". Retrieved 2024-01-22.
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. Retrieved 11 June 2012.
6. WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
7. 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.
8. "Southern Association of Forensic Scientists". Archived from the original on 2014-09-10. Retrieved 2013-07-16.
9. Controlled Substances listed by the DEA