Chemistry:AM-694
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Short description: Chemical compound
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| Formula | C20H19FINO |
| Molar mass | 435.281 g·mol−1 |
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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 Ki of 0.08 nM at CB1 and 18 times selectivity over CB2 with a Ki 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]
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
- ↑ 1.0 1.1 "Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand". Journal of Labelled Compounds and Radiopharmaceuticals 46 (9): 799–804. August 2003. doi:10.1002/jlcr.720.
- ↑ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
- ↑ "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. February 2013. doi:10.1002/dta.1336. PMID 22522907.
- ↑ "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. July 2020. doi:10.1021/acs.chemrestox.9b00466. PMID 32301604.
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