AM-679 (cannabinoid): Difference between revisions

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Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors o
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{{Short description|Chemical compound}}
{{about|the cannabinoid agonist|the FLAP inhibitor|AM-679 (FLAP inhibitor)}}
{{about|the cannabinoid agonist|the FLAP inhibitor|AM-679 (FLAP inhibitor)}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 443845870
| verifiedrevid = 451565677
| IUPAC_name = 1-pentyl-3-(2-iodobenzoyl)indole
| IUPAC_name = (2-Iodophenyl)(1-pentyl-1''H''-indol-3-yl)methanone
| image = AM-679_structure.png
| image = AM-679_structure.png
| width = 200
| width = 200
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| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = Class B
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| legal_status =
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number =
| CAS_number = 335160-91-3
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25991468
| ChemSpiderID = 25991468
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 61TFT4BO1C


<!--Chemical data-->
<!--Chemical data-->
| C=20 | H=20 | I=1 | N=1 | O=1
| C=20 | H=20 | I=1 | N=1 | O=1
| molecular_weight = 417.283 g/mol
| smiles = Ic1ccccc1C(=O)c(c2ccccc23)cn3CCCCC
| smiles = Ic1ccccc1C(=O)c(c2ccccc23)cn3CCCCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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}}
}}


'''AM-679''' is a drug which acts as a moderately potent [[agonist]] for the [[cannabinoid receptor]]s, with a [[Dissociation constant|K<sub>i</sub>]] of 13.5nM at [[Cannabinoid receptor 1|CB<sub>1</sub>]] and 49.5nM at [[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 | assign1= }}</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 which are now widely used in research, including the potent CB<sub>1</sub> agonists [[AM-694]] and [[AM-2233]], and the selective CB<sub>2</sub> agonist [[AM-1241]].<ref>[http://proquest.umi.com/pqdlink?did=726066941&Fmt=7&clientId=79356&RQT=309&VName=PQD Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.]</ref> 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.<ref name="pmid21813254">{{cite journal |author=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= |issue= |pages= |year=2011 |month=August |pmid=21813254 |doi=10.1016/j.forsciint.2011.07.011 |url=}}</ref>
'''AM-679''' (part of the [[List of AM cannabinoids|AM cannabinoid series]]) is a drug that acts as a moderately potent [[agonist]] for the [[cannabinoid receptor]]s, with a [[Dissociation constant|''K''<sub>i</sub>]] of 13.5&nbsp;nM at [[Cannabinoid receptor 1|CB<sub>1</sub>]] and 49.5&nbsp;nM at [[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 [[AM-694]] and [[AM-2233]], and the selective CB<sub>2</sub> agonist [[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 [[cannabinoid]] [[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==
== See also ==
* [[RCS-4]]
* [[RCS-4]]
* [[AM-694]]
* [[AM-2233]]


==References==
== References ==
{{reflist}}
<references/>


{{Cannabinoids}}
{{Cannabinoids}}


⚫
[[Category:Cannabinoids]]
[[Category:Benzoylindoles]]
[[Category:Benzoylindoles]]
[[Category:AM cannabinoids]]
[[Category:AM cannabinoids]]
[[Category:Organoiodides]]
[[Category:Iodobenzene derivatives]]
⚫
[[Category:Designer drugs]]




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