JWH-250

JWH-250
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule II; DE: Anlage II; UK: Class B; US: Schedule I; Illegal in Czech Republic and Latvia;
Identifiers
	IUPAC name 2-(2-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone;
CAS Number	864445-43-2 ;
PubChem CID	44397540;
ChemSpider	23256117 ;
UNII	IP9911R8A0;
ChEMBL	ChEMBL188031 ;
CompTox Dashboard (EPA)	DTXSID40235556 ;
Chemical and physical data
Formula	C22H25NO2
Molar mass	335.447 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC;
	InChI 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 ; Key:FFLSJIQJQKDDCM-UHFFFAOYSA-N ;
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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 K_i 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.^[4] Other 2'-substituted analogues such as the methyl, chloro and bromo compounds are also active and somewhat more potent.^[5]^[6]

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 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.^[7] An ELISA immunoassay technique for detecting JWH-250 in urine has been reported.^[8]

Legal status

Australia

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

United States

In the United States, CB₁ receptor agonists of the 3-phenylacetylindole class such as JWH-250 are Schedule I Controlled Substances.^[10]

References

^ "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.
^ 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.
^ Legal article in Latvian (www.likumi.lv)
^ 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.
^ 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.
^ The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. ISBN 978-1-58829-712-9
^ "Understanding the 'Spice' phenomenon. EMCDDA, Lisbon, November 2009" (PDF). Archived from the original (PDF) on 2010-04-08. Retrieved 2009-11-05.
^ 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.
^ ^a ^b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
^ 21 U.S.C. § 812: Schedules of controlled substances

[1] "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.

[2] 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.

[3] Legal article in Latvian (www.likumi.lv)

[4] 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.

[5] 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.

[6] The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. ISBN 978-1-58829-712-9

[7] "Understanding the 'Spice' phenomenon. EMCDDA, Lisbon, November 2009" (PDF). Archived from the original (PDF) on 2010-04-08. Retrieved 2009-11-05.

[8] 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.

[Poisons_Standard-9] Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

[10] 21 U.S.C. § 812: Schedules of controlled substances

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