View source for Chemistry:AM-679 (cannabinoid)

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451565677
| IUPAC_name = (2-Iodophenyl)(1-pentyl-1''H''-indol-3-yl)methanone
| image = AM-679_structure.png
| width = 200

<!--Clinical data-->
| tradename =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =  
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = Class B
| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status =  
| routes_of_administration =  

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
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<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 335160-91-3 
| ATC_prefix =  
| ATC_suffix =  
| PubChem =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =  
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25991468
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 61TFT4BO1C

<!--Chemical data-->
| 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
}}

'''AM-679''' (part of the AM cannabinoid series) is a drug that acts as a moderately potent [[Biology:Agonist|agonist]] for the [[Biology:Cannabinoid receptor|cannabinoid receptor]]s, with a [[Chemistry:Dissociation constant|''K''<sub>i</sub>]] of 13.5&nbsp;nM at [[Biology:Cannabinoid receptor 1|CB<sub>1</sub>]] and 49.5&nbsp;nM at [[Biology:Cannabinoid receptor 2|CB<sub>2</sub>]].<ref name="WO 2001 28557 A1">{{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 }}</ref> 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 CB<sub>1</sub> agonists [[Chemistry:AM-694|AM-694]] and [[Chemistry:AM-2233|AM-2233]], and the selective CB<sub>2</sub> agonist [[Chemistry:AM-1241|AM-1241]].<ref>{{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}} }}</ref> AM-679 was first identified as having been sold as a [[Chemistry:Cannabinoid|cannabinoid]] [[Chemistry:Designer drug|designer drug]] in Hungary in 2011, along with another novel compound 1-pentyl-3-(1-adamantoyl)indole.<ref name="pmid21813254">{{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 }}</ref>

== See also ==
* [[Chemistry:RCS-4|RCS-4]]

== References ==
{{reflist}}

{{Cannabinoids}}

[[Category:Benzoylindoles]]
[[Category:Iodoarenes]]
[[Category:Designer drugs]]


{{Sourceattribution|AM-679 (cannabinoid)}}