Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459449749
| verifiedrevid = 459449749
| IUPAC_name = (4-methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone
| IUPAC_name = (4-Methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone
| image = JWH-122.svg
| image = JWH-122.svg
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 619294-47-2
| CAS_number = 619294-47-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 44147RI31X
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22796
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
Line 15: Line 21:
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 24623066
| ChemSpiderID = 24623066
| C = 25 | H = 25 | N = 1 | O = 1
| chemical_formula = C<sub>25</sub>H<sub>25</sub>NO
| molecular_weight = 355.472
| smiles = CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(c4c3cccc4)C
| smiles = CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(c4c3cccc4)C
| InChI = 1/C25H25NO/c1-3-4-9-16-26-17-23(21-12-7-8-13-24(21)26)25(27)22-15-14-18(2)19-10-5-6-11-20(19)22/h5-8,10-15,17H,3-4,9,16H2,1-2H3
| InChIKey = HUKJQMKQFWYIHS-UHFFFAOYAB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H25NO/c1-3-4-9-16-26-17-23(21-12-7-8-13-24(21)26)25(27)22-15-14-18(2)19-10-5-6-11-20(19)22/h5-8,10-15,17H,3-4,9,16H2,1-2H3
| StdInChI = 1S/C25H25NO/c1-3-4-9-16-26-17-23(21-12-7-8-13-24(21)26)25(27)22-15-14-18(2)19-10-5-6-11-20(19)22/h5-8,10-15,17H,3-4,9,16H2,1-2H3
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| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
| pregnancy_category=
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU = 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, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_CA = Schedule II
| legal_UK = Class B
| legal_status =
| legal_US = Schedule I
| legal_DE = Anlage II
| routes_of_administration =
| routes_of_administration =
}}
}}


'''JWH-122''' is a synthetic cannabimimetic that was discovered by [[John W. Huffman]]. It is a methylated analogue of [[JWH-018]]. It has a [[Dissociation constant|K<sub>i</sub>]] of 0.69 nM at CB<sub>1</sub> and 1.2 nM at CB<sub>2</sub>.<ref>{{Cite pmid|15582455}}</ref>
'''JWH-122''' is a synthetic cannabimimetic that was discovered by [[John W. Huffman]]. It is a methylated analogue of [[JWH-018]]. It has a [[Dissociation constant|K<sub>i</sub>]] of 0.69 nM at CB<sub>1</sub> and 1.2 nM at CB<sub>2</sub>.<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>


In January 2015, over 40 people were reportedly sickened after eating a holiday bread called [[Rosca de reyes]] purchased at a bakery in [[Santa Ana, California]], that was laced with JWH-122.<ref>{{Cite web | url=http://www.foodsafetynews.com/2015/02/tests-show-synthetic-drug-contaminated-holiday-bread-from-ca-bakery/ |title = Tests Show Synthetic Drug Contaminated Holiday Bread from CA Bakery|date = 2015-02-02 | work = Food Safety News }}</ref>


==See also===
==Legal status==
===Australia===
JWH-122 is considered a Schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">{{cite web | title = Poisons Standard | date = October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 | work = Federal Register of Legislation | publisher = The Australian Government }}</ref> A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name="Poisons Standard" />

===China===
As of October 2015 JWH-122 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>

===United States===
In the United States, JWH-122 is a [[Schedule I Controlled Substance]].<ref>{{cite web | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf | title = Controlled Substances | work = Diversion Control Division | publisher = U.S. Department of Justice, Drug Enforcement Division (DEA) }}</ref>

== See also ==
* [[JWH-193]]
* [[JWH-193]]
* [[JWH-210]]
* [[JWH-210]]
* [[JWH-398]]
* [[JWH-398]]
* [[List of JWH cannabinoids]]


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


{{Cannabinoids}}
{{Cannabinoids}}


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

[[Category:CB2 receptor agonists]]
[[de:JWH-122]]

{{cannabinoid-stub}}

Latest revision as of 04:06, 4 January 2024

JWH-122
Legal status
Legal status
Identifiers
  • (4-Methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone
CAS Number
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25NO
Molar mass355.481 g·mol−1
3D model (JSmol)
  • CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(c4c3cccc4)C
  • InChI=1S/C25H25NO/c1-3-4-9-16-26-17-23(21-12-7-8-13-24(21)26)25(27)22-15-14-18(2)19-10-5-6-11-20(19)22/h5-8,10-15,17H,3-4,9,16H2,1-2H3 checkY
  • Key:HUKJQMKQFWYIHS-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

JWH-122 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is a methylated analogue of JWH-018. It has a Ki of 0.69 nM at CB1 and 1.2 nM at CB2.[2]

In January 2015, over 40 people were reportedly sickened after eating a holiday bread called Rosca de reyes purchased at a bakery in Santa Ana, California, that was laced with JWH-122.[3]

Legal status[edit]

Australia[edit]

JWH-122 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[4] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[4]

China[edit]

As of October 2015 JWH-122 is a controlled substance in China.[5]

United States[edit]

In the United States, JWH-122 is a Schedule I Controlled Substance.[6]

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. ^ 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.
  3. ^ "Tests Show Synthetic Drug Contaminated Holiday Bread from CA Bakery". Food Safety News. 2015-02-02.
  4. ^ a b "Poisons Standard". Federal Register of Legislation. The Australian Government. October 2015.
  5. ^ "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.
  6. ^ "Controlled Substances" (PDF). Diversion Control Division. U.S. Department of Justice, Drug Enforcement Division (DEA).
source: https://en.wikipedia.org/w/index.php?title=JWH-122&diff=1193502445&oldid=535791733

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