Cannabis Ruderalis

thcscience_admin
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
Mdog228 (talk | contribs)
1 edit
SSCreader (talk | contribs)
269 edits
mNo edit summary
 
(40 intermediate revisions by 27 users not shown)
Line 1: Line 1:
{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 451554694
| verifiedrevid = 451554694
| IUPAC_name = 4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone
| IUPAC_name = 4-Ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone
| image = JWH-210_structure.png
| image = JWH-210.svg
| width = 180


<!--Clinical data-->
<!--Clinical data-->
Line 10: Line 13:
| 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_BR = F2
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| 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>
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_CA = Schedule II
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_UK = Class B
⚫
| 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 | accessdate = 12 June 2011}}</ref>
| legal_US = Schedule I
⚫
| routes_of_administration =
| legal_DE = Anlage II
⚫
| 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>
⚫
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
Line 21: Line 27:
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 824959-81-1
| CAS_number = 824959-81-1
| CAS_supplemental = (JWH-210)<br /> 619294-47-2 (JWH-122)
| CAS_supplemental = (JWH-210)<br /> {{CAS|824960-02-3}} (JWH-182)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R18JYO04PY
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
Line 32: Line 40:
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 24617616


<!--Chemical data-->
<!--Chemical data-->
| C=26 | H=27 | N=1 | O=1
| C=26 | H=27 | N=1 | O=1
| molecular_weight = 369.498 g/mol
| smiles = c4cccc2c4c(CC)ccc2C(=O)c(c3)c1ccccc1n3CCCCC
| smiles = c4cccc2c4c(CC)ccc2C(=O)c(c3)c1ccccc1n3CCCCC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = LACIUQLUNACUKC-UHFFFAOYSA-N
}}
}}


'''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 0.46nM at CB<sub>1</sub> and 0.69nM 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> 0.69nM) and [[JWH-182]] (CB<sub>1</sub> K<sub>i</sub> 0.65nM) respectively, and than the 4-methoxy compound [[JWH-081]] (CB<sub>1</sub> K<sub>i</sub> 1.2nM).<ref>{{Cite pmid|15582455}}</ref> It was discovered by and named after Dr. [[John W. Huffman]]. JWH-210 and JWH-122 were banned in Sweden on 1st 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>[http://www.lagboken.se/files/SFS/2010/101086.PDF Swedish Code of Statutes Regulation (2010:1086). (pdf)]</ref> The substance 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>
'''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&nbsp;nM at CB<sub>1</sub> and 0.69&nbsp;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&nbsp;nM) and JWH-182 (CB<sub>1</sub> K<sub>i</sub> 0.65&nbsp;nM) respectively, and than the 4-methoxy compound [[JWH-081]] (CB<sub>1</sub> K<sub>i</sub> 1.2&nbsp;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]].


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>
Effects
Out of all the JWH chemicals, JWH-210 is most known to produce effects similar to that of a sativa-type cannabis. <ref>{{cite web|first=CulianJope|title=Re: Jwh-210 Experiences|url=http://www.drugs-forum.com/forum/showthread.php?t=140647|accessdate=7 November 2011}}</ref>


==See also==
==Legal status==
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>

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>

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>

== See also ==
*[[JWH-081]]
*[[JWH-081]]
*[[JWH-193]]
*[[JWH-193]]
*[[JWH-398]]
*[[JWH-398]]


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



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


[[Category:JWH cannabinoids]]
[[Category:JWH cannabinoids]]
[[Category:Naphthoylindoles]]
[[Category:Naphthoylindoles]]
[[Category:Designer drugs]]

[[Category:CB1 receptor agonists]]
[[ru:JWH-210]]
[[Category:CB2 receptor agonists]]

Latest revision as of 23:17, 18 September 2023

JWH-210
Legal status
Legal status
Identifiers
  • 4-Ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.233.380 Edit this at Wikidata
Chemical and physical data
FormulaC26H27NO
Molar mass369.508 g·mol−1
3D model (JSmol)
  • c4cccc2c4c(CC)ccc2C(=O)c(c3)c1ccccc1n3CCCCC
  • InChI=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 ☒N
  • Key:LACIUQLUNACUKC-UHFFFAOYSA-N ☒N
 ☒NcheckY (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]

  1. ^ 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.
  2. ^ "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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 21 U.S.C. § 812: Schedules of controlled substances
  6. ^ Swedish Code of Statutes Regulation (2010:1086).
  7. ^ "Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.
  8. ^ LVFS 2011:8
  9. ^ "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.
source: https://en.wikipedia.org/w/index.php?title=JWH-210&diff=1176020601&oldid=459392896

Leave a Reply