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AM-2201

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) NZ: Temporary Class UK: Class B US: Schedule I UN: Psychotropic Schedule II
Identifiers
IUPAC name 1--(naphthalen-1-yl)methanone
CAS Number	335161-24-5
PubChem CID	53393997
ChemSpider	24751884
UNII	TBJ0966F1O
KEGG	C22771
CompTox Dashboard (EPA)	DTXSID50187158
Chemical and physical data
Formula	C24H22FNO
Molar mass	359.444 g·mol
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 Key:ALQFAGFPQCBPED-UHFFFAOYSA-N
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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 K_i 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.

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

• Naphthoylindoles
• Organofluorides
• AM cannabinoids
• Designer drugs
• CB1 receptor agonists
• CB2 receptor agonists