AM-694
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 477235914
| IUPAC_name = 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone
| image = AM-694-2D-skeletal.svg
| image_class = skin-invert-image
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU = S9
| legal_CA = Schedule II
| legal_UK = Class B
| legal_US = Schedule I
| legal_DE = Anlage II
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 335161-03-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6RK7KN7L1O
| ATC_prefix =
| ATC_suffix =
| PubChem = 9889172
| ChEBI = 138017
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8064843
| C=20 | H=19 | F=1 | I=1 | N=1 | O=1
| smiles = Ic2ccccc2C(=O)c1cn(CCCCCF)c3ccccc13
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LFFIIZFINPPEMC-UHFFFAOYSA-N
}}
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.{{cite journal | vauthors = Willis PG, Katoch-Rouse R, Horti AG | title = Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand | journal = Journal of Labelled Compounds and Radiopharmaceuticals | date = August 2003 | volume = 46 | issue = 9 | pages = 799–804 | doi = 10.1002/jlcr.720 }}
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.{{Ref patent2 | country = WO | number = 200128557 | status = granted | title = Cannabimimetic indole derivatives | pubdate = 2001-04-26 | gdate = 2001-06-07 | pridate= 1999-10-18 | inventor = Makriyannis A, Deng H | assign1= }} 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.
Metabolism
Pathways of metabolism include hydrolytic defluorination, carboxylation, and monohydroxylation of the N-alkyl chain.{{cite journal | vauthors = Grigoryev A, Kavanagh P, Melnik A | title = 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 | journal = Drug Testing and Analysis | volume = 5 | issue = 2 | pages = 110–5 | date = February 2013 | pmid = 22522907 | doi = 10.1002/dta.1336 }}{{cite journal | vauthors = Apirakkan O, Gavrilović I, Cowan DA, Abbate V | title = In Vitro Phase I Metabolic Profiling of the Synthetic Cannabinoids AM-694, 5F-NNEI, FUB-APINACA, MFUBINAC, and AMB-FUBINACA | journal = Chemical Research in Toxicology | volume = 33 | issue = 7 | pages = 1653–1664 | date = July 2020 | pmid = 32301604 | doi = 10.1021/acs.chemrestox.9b00466 | s2cid = 215803607 }}