AM-694

AM-694
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone;
CAS Number	335161-03-0 ;
PubChem CID	9889172;
ChemSpider	8064843 ;
UNII	6RK7KN7L1O;
ChEBI	CHEBI:138017;
CompTox Dashboard (EPA)	DTXSID30187156 ;
Chemical and physical data
Formula	C20H19FINO
Molar mass	435.281 g·mol−1
3D model (JSmol)	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 ; Key:LFFIIZFINPPEMC-UHFFFAOYSA-N ;
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AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a designer 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.^[1]

Pharmacology

AM-694 is an agonist for cannabinoid receptors. It has a K_i of 0.08 nM at CB₁ and 18 times selectivity over CB₂ with a K_i of 1.44 nM.^[2] 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.^[1]

Metabolism

Pathways of metabolism include hydrolytic defluorination, carboxylation, and monohydroxylation of the N-alkyl chain.^[3]^[4]

References

^ ^a ^b Willis PG, Katoch-Rouse R, Horti AG (August 2003). "Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand". Journal of Labelled Compounds and Radiopharmaceuticals. 46 (9): 799–804. doi:10.1002/jlcr.720.
^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
^ Grigoryev A, Kavanagh P, Melnik A (February 2013). "The detection of the urinary metabolites of 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (AM-694), a high affinity cannabimimetic, by gas chromatography - mass spectrometry". Drug Testing and Analysis. 5 (2): 110–5. doi:10.1002/dta.1336. PMID 22522907.
^ Apirakkan O, Gavrilović I, Cowan DA, Abbate V (July 2020). "In Vitro Phase I Metabolic Profiling of the Synthetic Cannabinoids AM-694, 5F-NNEI, FUB-APINACA, MFUBINAC, and AMB-FUBINACA". Chemical Research in Toxicology. 33 (7): 1653–1664. doi:10.1021/acs.chemrestox.9b00466. PMID 32301604. S2CID 215803607.

[Willis-1] Willis PG, Katoch-Rouse R, Horti AG (August 2003). "Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand". Journal of Labelled Compounds and Radiopharmaceuticals. 46 (9): 799–804. doi:10.1002/jlcr.720.

[WO_2001_28557_A1-2] WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07

[3] Grigoryev A, Kavanagh P, Melnik A (February 2013). "The detection of the urinary metabolites of 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (AM-694), a high affinity cannabimimetic, by gas chromatography - mass spectrometry". Drug Testing and Analysis. 5 (2): 110–5. doi:10.1002/dta.1336. PMID 22522907.

[pmid32301604-4] Apirakkan O, Gavrilović I, Cowan DA, Abbate V (July 2020). "In Vitro Phase I Metabolic Profiling of the Synthetic Cannabinoids AM-694, 5F-NNEI, FUB-APINACA, MFUBINAC, and AMB-FUBINACA". Chemical Research in Toxicology. 33 (7): 1653–1664. doi:10.1021/acs.chemrestox.9b00466. PMID 32301604. S2CID 215803607.

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AM-694

Pharmacology

Metabolism

See also

References

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