JWH-424: Difference between revisions

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Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (
Importing Wikidata short description: "Chemical compound"
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 416695546
| verifiedrevid = 433533861
| IUPAC_name = 1-pentyl-3-(8-bromo-1-naphthoyl)indole
| IUPAC_name = 1-Pentyl-3-(8-bromo-1-naphthoyl)indole
| image = JWH-424_structure.png
| image = JWH-424.svg
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| CAS_number =
| width = 150
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| ATC_prefix =

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| ATC_suffix =
<!--Clinical data-->
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| PubChem =
| DrugBank =
| tradename =
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| C=24|H=22|Br=1|N=1|O=1
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| pregnancy_US = <!-- A / B / C / D / X -->
| molecular_weight = 420.341 g/mol
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| pregnancy_category =
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| smiles = c4cccc1c4n(CCCCC)cc1C(=O)c(c2c3Br)cccc2ccc3
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| bioavailability =
| legal_CA = Schedule II
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| protein_bound =
| legal_DE = NpSG
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| metabolism =
| legal_UK = Class B
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| elimination_half-life =
| legal_US = Schedule I
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| excretion =
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| legal_status =
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| routes_of_administration =
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| pregnancy_US = <!-- A / B / C / D / X -->

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| pregnancy_category=
<!--Pharmacokinetic data-->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| bioavailability =
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
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| protein_bound =
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
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| metabolism =
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| elimination_half-life =
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| legal_status =
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| excretion =
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| routes_of_administration =

<!--Identifiers-->
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| CAS_number = 1366068-04-3
| CAS_number_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O4Q3AIP6BJ
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| ATC_prefix =
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| ATC_suffix =
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| PubChem = 57458937
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID = 28645324

<!--Chemical data-->
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| C=24 | H=22 | Br=1 | N=1 | O=1
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| smiles = c4cccc1c4n(CCCCC)cc1C(=O)c(c2c3Br)cccc2ccc3
| StdInChI = 1S/C24H22BrNO/c1-2-3-6-15-26-16-20(18-11-4-5-14-22(18)26)24(27)19-12-7-9-17-10-8-13-21(25)23(17)19/h4-5,7-14,16H,2-3,6,15H2,1H3
| StdInChIKey = QXZYVJRMQVOOEQ-UHFFFAOYSA-N

}}
}}


'''JWH-424''' is a drug from the [[naphthoylindole]] family, which acts as a [[cannabinoid]] agonist at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2|CB<sub>2</sub>]] [[Receptor (biochemistry)|receptors]], but with moderate selectivity for CB<sub>2</sub>, having a [[Dissociation constant#Protein-ligand binding|K<sub>i</sub>]] of 5.44nM at CB<sub>2</sub> vs 20.9nM at CB<sub>1</sub>. The heavier 8-[[iodo]] analogue is even more CB<sub>2</sub> selective, with its 2-methyl derivative having 40x selectivity for CB<sub>2</sub>. However the 1-propyl homologues in this series showed much lower affinity at both receptors, reflecting a generally reduced affinity for the 8-substituted naphthoylindoles overall.<ref>Valerie Smith, John Huffman, Jenny Wiley and Billy Martin. EFFECTS OF HALOGEN SUBSTITUENTS UPON CB1 AND CB2 RECEPTOR AFFINITIES IN THE SERIES OF N-ALKYL-3-(8-HALO-1-NAPTHOYL)INDOLES. (2007) 17th Annual Symposium on the Cannabinoids, Burlington, Vermont, International Cannabinoid Research Society, Page 72.</ref><ref>John W. Huffman, Valerie J. Smith, Jianhong Chen, Jenny L. Wiley and Billy R. Martin. STRUCTURE-ACTIVITY RELATIONSHIPS AT THE CB1 AND CB2 RECEPTORS FOR 1-ALKYL-3-(1-NAPHTHOYL-4 AND 8-HALOGEN SUBSTITUTED) INDOLES (2009) 19th Annual Symposium on the Cannabinoids, Burlington, Vermont, International Cannabinoid Research Society, Page 2.</ref>
'''JWH-424''' is a drug from the [[naphthoylindole]] family, which acts as a [[cannabinoid]] [[agonist]] at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2|CB<sub>2</sub>]] [[Receptor (biochemistry)|receptors]], but with moderate selectivity for CB<sub>2</sub>, having a [[Dissociation constant#Protein-ligand binding|K<sub>i</sub>]] of 5.44nM at CB<sub>2</sub> vs 20.9&nbsp;nM at CB<sub>1</sub>. The heavier 8-[[Iodine|iodo]] analogue is even more CB<sub>2</sub> selective, with its 2-methyl derivative having 40 times selectivity for CB<sub>2</sub>. However the 1-propyl homologues in this series showed much lower affinity at both receptors, reflecting a generally reduced affinity for the 8-substituted naphthoylindoles overall.<ref name="pmid22341572">{{cite journal | vauthors = Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW | title = Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents | journal = Bioorganic & Medicinal Chemistry | volume = 20 | issue = 6 | pages = 2067–81 | date = March 2012 | pmid = 22341572 | pmc = 3298571 | doi = 10.1016/j.bmc.2012.01.038 }}</ref>

In the United States, all CB<sub>1</sub> receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-424 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>


==See also==
==See also==
* [[JWH-018]]
* [[JWH-398]]
* [[JWH-398]]


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


{{Cannabinoids}}
{{Cannabinoids}}
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{{cannabinoid-stub}}


[[Category:Naphthoylindoles]]
[[Category:Naphthoylindoles]]
[[Category:JWH cannabinoids]]
[[Category:JWH cannabinoids]]
[[Category:Organobromides]]
[[Category:Bromoarenes]]
[[Category:Designer drugs]]
[[Category:CB1 receptor agonists]]

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{{cannabinoid-stub}}
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