AM-694

AM-694

Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule II DE: Anlage II (Prohibited) US: Schedule I
Identifiers
IUPAC name 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone
CAS Number	335161-03-0 N
PubChem (CID)	9889172
ChemSpider	8064843 Y
Chemical and physical data
Formula	C20H19FINO
Molar mass	435.273 g/mol
3D model (Jmol)	Interactive image
SMILES Ic2ccccc2C(=O)c1cn(CCCCCF)c3ccccc13
InChI InChI=1S/C20H19FINO/c21-12-6-1-7-13-23-14-17(15-8-3-5-11-19(15)23)20(24)16-9-2-4-10-18(16)22/h2-5,8-11,14H,1,6-7,12-13H2 Y Key:LFFIIZFINPPEMC-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB₁. It is used in scientific research for mapping the distribution of CB₁ receptors. No public data about AM-694 metabolism is known. AM-694 has already emerged as a designer drug.

Pharmacology

AM-694 is an agonist for cannabinoid receptors. Affinities are: with a K_i of 0.08 nM at CB₁ and 18x selectivity over CB₂ with a K_i of 1.44 nM.^[1] It is unclear what is responsible for this unusually high CB₁ binding affinity, but it makes the ¹⁸F radiolabelled derivative of AM-694 useful for mapping the distribution of CB₁ receptors in the body.^[2]

Pharmacokinetics

AM-694 metabolism differs only slightly from that of JWH-018. AM-694 N-dealkylation produces fluoropentane instead of pentane (or plain alkanes in general). It has been speculated that the fluoropentane might function as an alkylating agent or is further metabolized into toxic fluoroacetic acid. This is not true since fluoroalkanes do not act as alkylating agents under normal conditions and uneven fluoroalkane chains metabolize into substantially less toxic fluoropropanoic acid.^[3][4]

See also

• AM-679
• AM-1235
• AM-2201
• AM-2232
• AM-2233
• FUBIMINA
• JWH-018
• List of AM cannabinoids
• List of JWH cannabinoids
• THJ-2201

References

1. ↑ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
2. ↑ Willis PG, Katoch-Rouse R, Horti AG. Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand. Journal of Labelled Compounds and Radiopharmaceuticals 2003;46(9):799-804. doi:10.1002/jlcr.720
3. ↑ Millington JE, Pattison FLM. TOXIC FLUORINE COMPOUNDS: XII. ESTERS OF ω-FLUOROALCOHOLS. Canadian Journal of Chemistry. 1956 Nov;34(11):1532-1541.
4. ↑ Pattison FLM, Howell WC, Woolford RG. TOXIC FLUORINE COMPOUNDS: XIII. ω-FLUOROALKYL ETHERS. Canadian Journal of Chemistry. 1957 Feb;35(2):141-148.