AM-2201

AM-2201

Systematic (IUPAC) name
1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone
Clinical data
Legal status	US: Schedule I Temporary Class Drug (NZ)
Identifiers
CAS Registry Number	335161-24-5 Y
ChemSpider	24751884 Y
Chemical data
Formula	C24H22FNO
Molecular mass	359.44 g/mol
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
Y (what is this?)  (verify)

AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole) is a research chemical that acts as a potent but nonselective full agonist for the cannabinoid receptor.^[1] It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University.

Hazards

AM-2201 is widely regarded by recreational users of synthetic cannabinoids as one of the most potent and possibly the most potent substance available in this class of drugs. As the dosage is much smaller than other synthetic cannabinoids, accidental overdose becomes more likely. There have been anecdotal reports of individuals experiencing panic attacks and vomiting at doses as small as 2 mg. Convulsions have been reported^[2] including at doses as low as 10 mg.^[3] Caution should be taken if using this substance as it is active at doses as small as 500 µg, has a very steep dose-response curve, and tolerance builds up very quickly to the effects.

Recreational use of AM-2201 in the United States has led to it being specifically listed in a proposed 2011 amendment to the Controlled Substances Act, aiming to add a number of synthetic drugs into Schedule I.^[4] As of November 2011, there have been no reports of death associated with the drug. The acute toxicity and long term side effects associated with the use of AM-2201 are unknown.

Pharmacology

AM-2201 is a full agonist for cannabinoid receptors. Affinities are: with a K_i of 1.0nM at CB₁ and 2.6nM at CB₂.^[5] The 4-methyl functional analog MAM-2201 probably has similar affinities.

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.^[6]

See also

• AM-2233
• AM-694
• AM-1235
• AM-2232
• JWH-018
• THJ-2201

References

1. ↑ Wilkinson, S. M.; Banister, S. D.; Kassiou, M. (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry 68: 4. doi:10.1071/CH14198. 
2. ↑ David McQuade, Simon Hudson, Paul I. Dargan, David M. Wood (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): 373–376. doi:10.1007/s00228-012-1379-2. 
3. ↑ ekaJ (20 February 2011). "The Night I Killed My Friends". Erowid.org. Retrieved 11 June 2012. 
4. ↑ Synthetic Drug Control Act of 2011. H.R. 1254, 112th Congress, 1st Session (2011).
5. ↑ WO patent 0128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
6. ↑ Southern Association of Forensic Scientists