Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 401493943
| 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
⚫
| CAS_number = 210179-46-7

⚫
| ATC_prefix =
<!--Clinical data-->
⚫
| ATC_suffix =
| tradename =
⚫
| PubChem = 10547208
| DrugBank =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| C=25|H=25|N=1|O=2
⚫
| pregnancy_category =
| molecular_weight = 371.47 g/mol
⚫
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫
| smiles = CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4
| bioavailability =
| legal_BR = F2
| 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>
⚫
| protein_bound =
| legal_CA = Schedule II
⚫
| metabolism =
| legal_UK = Class B
⚫
| elimination_half-life =
| legal_US = Schedule I
⚫
| excretion =
| legal_DE = Anlage II
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| 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>
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| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| routes_of_administration =
⚫
| pregnancy_category=

⚫
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
<!--Pharmacokinetic data-->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| bioavailability =
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫
| protein_bound =
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| metabolism =
⚫
| 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|accessdate=12 June 2011}}</ref>
⚫
| elimination_half-life =
⚫
| routes_of_administration =
⚫
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
⚫
| CAS_number = 210179-46-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 77E58024IT
⚫
| ATC_prefix =
⚫
| ATC_suffix =
⚫
| PubChem = 10547208
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID = 8722599

<!--Chemical data-->
⚫
| C=25 | H=25 | N=1 | O=2
⚫
| 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, Griffin G, Huffman JW, Wu MJ, Keel C, Yang B, Showalter VM, Abood ME, Martin BR. 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, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, Thompson ALS, Bushell S, Tartal C, Hurst DP, Reggio PH, Selley DE, Cassidy MP, Wiley JL, Martin BR. 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 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}}
<references/>


{{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:CB1 receptor agonists]]

⚫
{{cannabinoid-stub}}

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=434771914

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