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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 406104785
| verifiedrevid = 406104785
| IUPAC_name = 2-(2-methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
| IUPAC_name = 2-(2-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
| image = JWH-250.svg
| image = JWH-250.svg


Line 11: Line 12:
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| 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 / Class A, B, C -->
| legal_CA = Schedule II
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_UK = Class B
| legal_US = Schedule I
| legal_DE = Anlage II
| legal_status = Illegal in Czech Republic and Latvia<ref>[http://www.likumi.lv/doc.php?id=201101&from=off Legal article in Latvian (www.likumi.lv)]</ref>
| legal_status = Illegal in Czech Republic and Latvia<ref>[http://www.likumi.lv/doc.php?id=201101&from=off Legal article in Latvian (www.likumi.lv)]</ref>
| routes_of_administration =
| 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 = 864445-43-2
| CAS_number = 864445-43-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IP9911R8A0
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
Line 34: Line 41:
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 188031
| ChEMBL = 188031
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 23256117


<!--Chemical data-->
<!--Chemical data-->
| C=22 | H=25 | N=1 | O=2
| C=22 | H=25 | N=1 | O=2
| molecular_weight = 335.439 g/mol
| smiles = COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC
| smiles = COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C22H25NO2/c1-3-4-9-14-23-16-19(18-11-6-7-12-20(18)23)21(24)15-17-10-5-8-13-22(17)25-2/h5-8,10-13,16H,3-4,9,14-15H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FFLSJIQJQKDDCM-UHFFFAOYSA-N

}}
}}


'''JWH-250''' or ('''1-pentyl-3-(2-methoxyphenylacetyl)indole''') is an [[analgesic]] chemical from the [[phenylacetylindole]] family, which acts as a [[cannabinoid]] [[agonist]] at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2 (macrophage)|CB<sub>2</sub>]] receptors, with a [[Dissociation constant|K<sub>i</sub>]] of 11nM at CB<sub>1</sub> and 33nM at CB<sub>2</sub>. Unlike many of the older [[List of JWH cannabinoids|JWH series]] compounds, this compound does not have a [[naphthalene]] ring, instead occupying this position with a 2'-methoxy-phenylacetyl group, making JWH-250 a representative member of a new class of cannabinoid ligands.<ref>{{cite journal | last1 = Huffman | first1 = JW | last2 = Szklennik | first2 = PV | last3 = Almond | first3 = A | last4 = Bushell | first4 = K | last5 = Selley | first5 = DE | last6 = He | first6 = H | last7 = Cassidy | first7 = MP | last8 = Wiley | first8 = JL | last9 = Martin | first9 = BR | title = 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles | journal = Bioorganic & medicinal chemistry letters | volume = 15 | issue = 18 | pages = 4110–3 | year = 2005 | pmid = 16005223 | author-separator =, | author-name-separator= | doi = 10.1016/j.bmcl.2005.06.008 }}</ref> Other 2'-substituted analogues such as the [[JWH-251|methyl]], [[JWH-203|chloro]] and [[JWH-249|bromo]] compounds are also active and somewhat more potent.<ref>{{cite journal | last1 = Manera | first1 = C | last2 = Tuccinardi | first2 = T | last3 = Martinelli | first3 = A | title = Indoles and related compounds as cannabinoid ligands | journal = Mini reviews in medicinal chemistry | volume = 8 | issue = 4 | pages = 370–87 | year = 2008 | pmid = 18473928 | author-separator =, | author-name-separator= }}</ref><ref>The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. ISBN 978-1-58829-712-9</ref>
'''JWH-250''' or ('''1-pentyl-3-(2-methoxyphenylacetyl)indole''') is an [[analgesic]] chemical from the [[phenylacetylindole]] family that acts as a [[cannabinoid]] [[agonist]] at both the [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2 (macrophage)|CB<sub>2</sub>]] receptors, with a [[Dissociation constant|''K''<sub>i</sub>]] of 11&nbsp;nM at CB<sub>1</sub> and 33&nbsp;nM at CB<sub>2</sub>. Unlike many of the older [[List of JWH cannabinoids|JWH series]] compounds, this compound does not have a [[naphthalene]] ring, instead occupying this position with a 2'-methoxy-phenylacetyl group, making JWH-250 a representative member of a new class of cannabinoid ligands.<ref>{{cite journal | vauthors = Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR | display-authors = 6 | title = 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles | journal = Bioorganic & Medicinal Chemistry Letters | volume = 15 | issue = 18 | pages = 4110–3 | date = September 2005 | pmid = 16005223 | doi = 10.1016/j.bmcl.2005.06.008 }}</ref> Other 2'-substituted analogues such as the [[JWH-251|methyl]], [[JWH-203|chloro]] and [[JWH-249|bromo]] compounds are also active and somewhat more potent.<ref>{{cite journal | vauthors = Manera C, Tuccinardi T, Martinelli A | title = Indoles and related compounds as cannabinoid ligands | journal = Mini Reviews in Medicinal Chemistry | volume = 8 | issue = 4 | pages = 370–87 | date = April 2008 | pmid = 18473928 | doi = 10.2174/138955708783955935 }}</ref><ref>The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. {{ISBN|978-1-58829-712-9}}</ref>


==History==
==History==
JWH-250 was discovered by, and named after the researcher [[John W. Huffman]]. He created JWH-250 and a number of other compounds to research the structure and function of the [[endocannabinoid]] system of [[mammal]]s. Samples of JWH-250 were first identified in May 2009 by the German Federal Criminal Police, as an ingredient in new generation "[[Spice (drug)|herbal smoking blends]]" that had been released since the banning of the original ingredients [[(C8)-CP 47,497]] and [[JWH-018]].<ref>{{Cite web |url=http://www.emcdda.europa.eu/attachements.cfm/att_80086_EN_Spice%20Thematic%20paper%20%E2%80%94%20final%20version.pdf |title=Understanding the 'Spice' phenomenon. EMCDDA, Lisbon, November 2009 |access-date=2009-11-05 |archive-date=2010-04-08 |archive-url=https://web.archive.org/web/20100408172523/http://www.emcdda.europa.eu/attachements.cfm/att_80086_EN_Spice%20Thematic%20paper%20%E2%80%94%20final%20version.pdf |url-status=dead }}</ref> An ELISA immunoassay technique for detecting JWH-250 in urine has been reported.<ref>{{cite journal | vauthors = Arntson A, Ofsa B, Lancaster D, Simon JR, McMullin M, Logan B | title = Validation of a novel immunoassay for the detection of synthetic cannabinoids and metabolites in urine specimens | journal = Journal of Analytical Toxicology | volume = 37 | issue = 5 | pages = 284–90 | date = June 2013 | pmid = 23625703 | doi = 10.1093/jat/bkt024 | doi-access = free }}</ref>
JWH-250 was discovered by, and named after the researcher Dr. [[John W. Huffman]]. He created JWH-250 and a number of other compounds to research the structure and function of the [[endocannabinoid]] system of [[mammal]]s.
Samples of JWH-250 were first identified in May 2009 by the German Federal Criminal Police, as an ingredient in new generation "[[Spice (drug)|herbal smoking blends]]" which had been released since the banning of the original ingredients [[(C8)-CP 47,497]] and [[JWH-018]].<ref>[http://www.emcdda.europa.eu/attachements.cfm/att_80086_EN_Spice%20Thematic%20paper%20%E2%80%94%20final%20version.pdf Understanding the ‘Spice’ phenomenon. EMCDDA, Lisbon, November 2009]</ref>


==Legal status==
Competition,consumer awareness of the active components,and recent market trends have driven down the capital needed to buy JWH and other research chemicals such as these to a few US dollars per gram on the retail and wholesale market market.
===Australia===
<ref>http://www.thechemicalbay.com/component/virtuemart/chemicalbay/research-chemicals/jwh-250.html Buy JWH and RCS-4</ref>
JWH-250 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">Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534</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" />

===United States===
In the United States, CB<sub>1</sub> receptor agonists of the 3-phenylacetylindole class such as JWH-250 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>

== See also ==
* [[AM-2201]]
⚫
* [[JWH-073]]
* [[JWH-200]]
* [[List of JWH cannabinoids]]
* [[List of AM cannabinoids]]
* [[MEPIRAPIM]]
* [[SDB-001]]
* [[THJ-2201]]


== References ==
== References ==
{{Reflist|2}}
{{Reflist}}


{{Hallucinogens}}
{{Hallucinogens}}
{{Analgesics}}
{{Analgesics}}
{{Cannabinoids}}
{{Cannabinoids}}
{{Cannabinoid-stub}}


[[Category:JWH cannabinoids]]
[[Category:JWH cannabinoids]]
[[Category:Phenylacetylindoles]]
[[Category:Phenylacetylindoles]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]
[[Category:Designer drugs]]

[[Category:CB1 receptor agonists]]
⚫
[[ru:JWH-250]]
[[Category:CB2 receptor agonists]]
[[Category:Pentyl compounds]]

Latest revision as of 14:20, 24 March 2024

JWH-250
Legal status
Legal status
Identifiers
  • 2-(2-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H25NO2
Molar mass335.447 g·mol−1
3D model (JSmol)
  • COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC
  • InChI=1S/C22H25NO2/c1-3-4-9-14-23-16-19(18-11-6-7-12-20(18)23)21(24)15-17-10-5-8-13-22(17)25-2/h5-8,10-13,16H,3-4,9,14-15H2,1-2H3 ☒N
  • Key:FFLSJIQJQKDDCM-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-250 or (1-pentyl-3-(2-methoxyphenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist at both the CB1 and CB2 receptors, with a Ki of 11 nM at CB1 and 33 nM at CB2. Unlike many of the older JWH series compounds, this compound does not have a naphthalene ring, instead occupying this position with a 2'-methoxy-phenylacetyl group, making JWH-250 a representative member of a new class of cannabinoid ligands.[3] Other 2'-substituted analogues such as the methyl, chloro and bromo compounds are also active and somewhat more potent.[4][5]

History

[edit]

JWH-250 was discovered by, and named after the researcher John W. Huffman. He created JWH-250 and a number of other compounds to research the structure and function of the endocannabinoid system of mammals. Samples of JWH-250 were first identified in May 2009 by the German Federal Criminal Police, as an ingredient in new generation "herbal smoking blends" that had been released since the banning of the original ingredients (C8)-CP 47,497 and JWH-018.[6] An ELISA immunoassay technique for detecting JWH-250 in urine has been reported.[7]

[edit]

Australia

[edit]

JWH-250 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[8] 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.[8]

United States

[edit]

In the United States, CB1 receptor agonists of the 3-phenylacetylindole class such as JWH-250 are Schedule I Controlled Substances.[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. ^ Legal article in Latvian (www.likumi.lv)
  3. ^ Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, et al. (September 2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4110–3. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223.
  4. ^ Manera C, Tuccinardi T, Martinelli A (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.
  5. ^ The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. ISBN 978-1-58829-712-9
  6. ^ "Understanding the 'Spice' phenomenon. EMCDDA, Lisbon, November 2009" (PDF). Archived from the original (PDF) on 2010-04-08. Retrieved 2009-11-05.
  7. ^ Arntson A, Ofsa B, Lancaster D, Simon JR, McMullin M, Logan B (June 2013). "Validation of a novel immunoassay for the detection of synthetic cannabinoids and metabolites in urine specimens". Journal of Analytical Toxicology. 37 (5): 284–90. doi:10.1093/jat/bkt024. PMID 23625703.
  8. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  9. ^ 21 U.S.C. § 812: Schedules of controlled substances
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