Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 446619973
| verifiedrevid = 446619973
| IUPAC_name = 4-methoxynaphthalen- 1-yl- (1-pentylindol- 3-yl)methanone
| IUPAC_name = 4-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
| image = JWH-081.svg
| image = JWH-081.svg


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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_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 = 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&#61;WDU20111050614 |publisher= Internetowy System Aktów Prawnych |accessdate= 12 June 2011}}</ref>
| legal_US = Schedule I
⚫
| routes_of_administration =
| legal_DE = Anlage II
⚫
| legal_status = 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-->
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 210179-46-7
| CAS_number = 210179-46-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 77E58024IT
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChemSpiderID = 8722599


<!--Chemical data-->
<!--Chemical data-->
| C=25 | H=25 | N=1 | O=2
| C=25 | H=25 | N=1 | O=2
| molecular_weight = 371.47 g/mol
| smiles = CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4
| smiles = CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4
| StdInChI = 1S/C25H25NO2/c1-3-4-9-16-26-17-22(19-11-7-8-13-23(19)26)25(27)21-14-15-24(28-2)20-12-6-5-10-18(20)21/h5-8,10-15,17H,3-4,9,16H2,1-2H3
| StdInChIKey = UBMPKJKGUQDHRM-UHFFFAOYSA-N

}}
}}
⚫
'''JWH-081''' is an [[analgesic]] chemical from the [[naphthoylindole]] family, which acts as a [[cannabinoid]] agonist at both the CB<sub>1</sub> and CB<sub>2</sub> receptors.<ref name="pmid10940540">{{cite journal | vauthors = Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, Showalter VM, Abood ME, Martin BR | display-authors = 6 | title = Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding | journal = Drug and Alcohol Dependence | volume = 60 | issue = 2 | pages = 133–40 | date = August 2000 | pmid = 10940540 | doi = 10.1016/s0376-8716(99)00152-0 }}</ref> With a [[dissociation constant|K<sub>i</sub>]] of 1.2nM it is fairly selective for the CB<sub>1</sub> subtype, its affinity at this subtype is measured at approximately 10x the affinity at CB<sub>2</sub>(12.4nM).<ref name="pmid15582455">{{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-081 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>
⚫
'''JWH-081''' is an [[analgesic]] chemical from the [[naphthoylindole]] family, which acts as a [[cannabinoid]] agonist at both the CB<sub>1</sub> and CB<sub>2</sub> receptors.<ref>Aung MM, ''et al.'' Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB<sub>1</sub> and CB<sub>2</sub> receptor binding. ''Drug and Alcohol Dependence'' 2000; 60:133-140.</ref> With a [[dissociation constant|K<sub>i</sub>]] of 1.2nM it is fairly selective for the CB<sub>1</sub> subtype, its affinity at this subtype approximately 10x the affinity at CB<sub>2</sub>.<ref>Huffman JW, ''et al.'' Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB<sub>1</sub> and CB<sub>2</sub> receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB<sub>2</sub> receptor agonists. ''Bioorganic and Medicinal Chemistry''. 2005; 13:89-112.</ref> It was discovered by and named after Dr. [[John W. Huffman]].


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

In the United States, JWH-081 is a [[Schedule I Controlled Substance]].<ref>[https://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf Controlled Substances listed by the DEA]</ref>

As of October 2015, JWH-081 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-018]]
*[[JWH-018]]
*[[JWH-098]]
*[[JWH-098]]
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*[[JWH-210]]
*[[JWH-210]]


==References==
== References ==
{{reflist}}
{{reflist}}


{{Cannabinoids}}
{{Cannabinoids}}
{{Hallucinogens}}
⚫
{{cannabinoid-stub}}


[[Category:Designer drugs]]
[[Category:JWH cannabinoids]]
[[Category:JWH cannabinoids]]
[[Category:Naphthoylindoles]]
[[Category:Naphthoylindoles]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]
[[Category:Designer drugs]]
[[Category:CB1 receptor agonists]]


⚫
{{cannabinoid-stub}}
[[pl:JWH-081]]

Latest revision as of 04:17, 28 August 2023

JWH-081
Legal status
Legal status
Identifiers
  • 4-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.230.181 Edit this at Wikidata
Chemical and physical data
FormulaC25H25NO2
Molar mass371.480 g·mol−1
3D model (JSmol)
  • CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4
  • InChI=1S/C25H25NO2/c1-3-4-9-16-26-17-22(19-11-7-8-13-23(19)26)25(27)21-14-15-24(28-2)20-12-6-5-10-18(20)21/h5-8,10-15,17H,3-4,9,16H2,1-2H3
  • Key:UBMPKJKGUQDHRM-UHFFFAOYSA-N
  (verify)

JWH-081 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors.[3] With a Ki of 1.2nM it is fairly selective for the CB1 subtype, its affinity at this subtype is measured at approximately 10x the affinity at CB2(12.4nM).[4] It was discovered by and named after John W. Huffman.

JWH-081 may be neurotoxic to animals when administered in high doses.[5]

Legal status[edit]

In the United States, JWH-081 is a Schedule I Controlled Substance.[6]

As of October 2015, JWH-081 is a controlled substance in China.[7]

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. ^ Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding". Drug and Alcohol Dependence. 60 (2): 133–40. doi:10.1016/s0376-8716(99)00152-0. PMID 10940540.
  4. ^ 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.
  5. ^ 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.
  6. ^ Controlled Substances listed by the DEA
  7. ^ "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-081&diff=1172605461&oldid=525174334

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