AM-679 (cannabinoid)
{{Short description|Chemical compound}}
{{about|the cannabinoid agonist|the FLAP inhibitor|AM-679 (FLAP inhibitor)}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451565677
| IUPAC_name = (2-Iodophenyl)(1-pentyl-1H-indol-3-yl)methanone
| image = AM-679_structure.png
| image_class = skin-invert-image
| width = 200
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| legal_AU =
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = Class B
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| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 335160-91-3
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25991468
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 61TFT4BO1C
| C=20 | H=20 | I=1 | N=1 | O=1
| smiles = Ic1ccccc1C(=O)c(c2ccccc23)cn3CCCCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H20INO/c1-2-3-8-13-22-14-17(15-9-5-7-12-19(15)22)20(23)16-10-4-6-11-18(16)21/h4-7,9-12,14H,2-3,8,13H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GAJBHYUAJOTAEW-UHFFFAOYSA-N
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AM-679 (part of the AM cannabinoid series) is a drug that acts as a moderately potent agonist for the cannabinoid receptors, with a Ki of 13.5 nM at CB1 and 49.5 nM at CB2.{{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 }} AM-679 was one of the first 3-(2-iodobenzoyl)indole derivatives that was found to have significant cannabinoid receptor affinity, and while AM-679 itself has only modest affinity for these receptors, it was subsequently used as a base to develop several more specialised cannabinoid ligands that are now widely used in research, including the potent CB1 agonists AM-694 and AM-2233, and the selective CB2 agonist AM-1241.{{cite thesis |type=PhD Dissertation |title=Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs | vauthors = Deng H |year=2000 |publisher=University of Connecticut |id={{ProQuest|304624325}} }} AM-679 was first identified as having been sold as a cannabinoid designer drug in Hungary in 2011, along with another novel compound 1-pentyl-3-(1-adamantoyl)indole.{{cite journal | vauthors = Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J | title = Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary | journal = Forensic Science International | volume = 214 | issue = 1–3 | pages = 27–32 | date = January 2012 | pmid = 21813254 | doi = 10.1016/j.forsciint.2011.07.011 }}