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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 451554694 |
| verifiedrevid = 451554694 |
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| IUPAC_name = 4- |
| IUPAC_name = 4-Ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone |
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| image = JWH- |
| image = JWH-210.svg |
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| width = 180 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_BR = F2 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_CA = Schedule II |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_UK = Class B |
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⚫ | | legal_status = Illegal in Sweden,I-N(Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | |
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| legal_US = Schedule I |
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| legal_DE = Anlage II |
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⚫ | | legal_status = Illegal in Sweden, I-N (Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | access-date = 12 June 2011}}</ref> |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 824959-81-1 |
| CAS_number = 824959-81-1 |
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| CAS_supplemental = (JWH-210)<br /> 824960-02-3 (JWH-182) |
| CAS_supplemental = (JWH-210)<br /> {{CAS|824960-02-3}} (JWH-182) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = R18JYO04PY |
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| ATC_prefix = |
| ATC_prefix = |
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| ATC_suffix = |
| ATC_suffix = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 24617616 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=26 | H=27 | N=1 | O=1 |
| C=26 | H=27 | N=1 | O=1 |
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| molecular_weight = 369.498 g/mol |
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| smiles = c4cccc2c4c(CC)ccc2C(=O)c(c3)c1ccccc1n3CCCCC |
| smiles = c4cccc2c4c(CC)ccc2C(=O)c(c3)c1ccccc1n3CCCCC |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C26H27NO/c1-3-5-10-17-27-18-24(22-13-8-9-14-25(22)27)26(28)23-16-15-19(4-2)20-11-6-7-12-21(20)23/h6-9,11-16,18H,3-5,10,17H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = LACIUQLUNACUKC-UHFFFAOYSA-N |
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}} |
}} |
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'''JWH-210''' is an [[analgesic]] chemical from the [[naphthoylindole]] family, which acts as a potent [[cannabinoid]] agonist at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2 (macrophage)|CB<sub>2</sub>]] receptors, with K<sub>i</sub> values of 0. |
'''JWH-210''' is an [[analgesic]] chemical from the [[naphthoylindole]] family, which acts as a potent [[cannabinoid]] agonist at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2 (macrophage)|CB<sub>2</sub>]] receptors, with K<sub>i</sub> values of 0.46 nM at CB<sub>1</sub> and 0.69 nM at CB<sub>2</sub>. It is one of the most potent 4-substituted naphthoyl derivatives in the naphthoylindole series, having a higher [[Dissociation constant#Protein-ligand binding|binding affinity]] (i.e. lower K<sub>i</sub>) at CB<sub>1</sub> than both its 4-methyl and 4-''n''-propyl [[homolog (chemistry)|homologue]]s [[JWH-122]] (CB<sub>1</sub> K<sub>i</sub> 0.69 nM) and JWH-182 (CB<sub>1</sub> K<sub>i</sub> 0.65 nM) respectively, and than the 4-methoxy compound [[JWH-081]] (CB<sub>1</sub> K<sub>i</sub> 1.2 nM).<ref>{{cite journal | vauthors = Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, Thompson AL, Bushell S, Tartal C, Hurst DP, Reggio PH, Selley DE, Cassidy MP, Wiley JL, Martin BR | display-authors = 6 | title = Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists | journal = Bioorganic & Medicinal Chemistry | volume = 13 | issue = 1 | pages = 89–112 | date = January 2005 | pmid = 15582455 | doi = 10.1016/j.bmc.2004.09.050 }}</ref> It was discovered by and named after [[John W. Huffman]]. |
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JWH-210 may be neurotoxic to animals when administered in high doses.<ref>{{cite journal | vauthors = Cha HJ, Seong YH, Song MJ, Jeong HS, Shin J, Yun J, Han K, Kim YH, Kang H, Kim HS | display-authors = 6 | title = Neurotoxicity of Synthetic Cannabinoids JWH-081 and JWH-210 | journal = Biomolecules & Therapeutics | volume = 23 | issue = 6 | pages = 597–603 | date = November 2015 | pmid = 26535086 | pmc = 4624077 | doi = 10.4062/biomolther.2015.057 }}</ref> |
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==Legal status== |
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In the United States, all CB<sub>1</sub> receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-210 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref> |
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JWH-210 and JWH-122 were banned in Sweden on 1 October 2010 as hazardous goods harmful to health, after being identified as ingredients in "herbal" [[synthetic cannabis]] products.<ref>[http://www.riksdagen.se/webbnav/index.aspx?nid=3911&bet=1999:58 Swedish Code of Statutes Regulation (2010:1086).]</ref><ref>{{Cite web |url=http://www.lagboken.se/files/SFS/2010/101086.PDF |title=Swedish Code of Statutes Regulation (2010:1086). (pdf) |access-date=2011-01-10 |archive-url=https://web.archive.org/web/20110728111705/http://www.lagboken.se/files/SFS/2010/101086.PDF |archive-date=2011-07-28 |url-status=dead }}</ref> The substances JWH-210, JWH-122 and [[JWH-203]] were classified as illegal drugs by the Swedish government as of 1 September 2011.<ref>LVFS 2011:8</ref> |
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As of October 2015 JWH-210 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | url-status=dead }}</ref> |
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⚫ | |||
*[[JWH-081]] |
*[[JWH-081]] |
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*[[JWH-193]] |
*[[JWH-193]] |
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*[[JWH-398]] |
*[[JWH-398]] |
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==References== |
== References == |
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{{reflist}} |
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<references/> |
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{{Cannabinoids}} |
{{Cannabinoids}} |
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[[Category:Naphthoylindoles]] |
[[Category:Naphthoylindoles]] |
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[[Category:Designer drugs]] |
[[Category:Designer drugs]] |
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[[Category:CB1 receptor agonists]] |
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[[Category:CB2 receptor agonists]] |
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{{cannabinoid-stub}} |
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[[de:JWH-210]] |
Latest revision as of 23:17, 18 September 2023
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Identifiers | |
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CAS Number |
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PubChem CID | |
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UNII | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.233.380 |
Chemical and physical data | |
Formula | C26H27NO |
Molar mass | 369.508 g·mol−1 |
3D model (JSmol) | |
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(what is this?) (verify) |
JWH-210 is an analgesic chemical from the naphthoylindole family, which acts as a potent cannabinoid agonist at both the CB1 and CB2 receptors, with Ki values of 0.46 nM at CB1 and 0.69 nM at CB2. It is one of the most potent 4-substituted naphthoyl derivatives in the naphthoylindole series, having a higher binding affinity (i.e. lower Ki) at CB1 than both its 4-methyl and 4-n-propyl homologues JWH-122 (CB1 Ki 0.69 nM) and JWH-182 (CB1 Ki 0.65 nM) respectively, and than the 4-methoxy compound JWH-081 (CB1 Ki 1.2 nM).[3] It was discovered by and named after John W. Huffman.
JWH-210 may be neurotoxic to animals when administered in high doses.[4]
Legal status[edit]
In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-210 are Schedule I Controlled Substances.[5]
JWH-210 and JWH-122 were banned in Sweden on 1 October 2010 as hazardous goods harmful to health, after being identified as ingredients in "herbal" synthetic cannabis products.[6][7] The substances JWH-210, JWH-122 and JWH-203 were classified as illegal drugs by the Swedish government as of 1 September 2011.[8]
As of October 2015 JWH-210 is a controlled substance in China.[9]
See also[edit]
References[edit]
- ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
- ^ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 12 June 2011.
- ^ Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
- ^ Cha HJ, Seong YH, Song MJ, Jeong HS, Shin J, Yun J, et al. (November 2015). "Neurotoxicity of Synthetic Cannabinoids JWH-081 and JWH-210". Biomolecules & Therapeutics. 23 (6): 597–603. doi:10.4062/biomolther.2015.057. PMC 4624077. PMID 26535086.
- ^ : Schedules of controlled substances
- ^ Swedish Code of Statutes Regulation (2010:1086).
- ^ "Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.
- ^ LVFS 2011:8
- ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.