JWH-250

JWH-250
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); 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 ;
	(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 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.^[3] Other 2'-substituted analogues such as the methyl, chloro and bromo compounds are also active and somewhat more potent.^[4]^[5]

^ 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

[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

[1]

[2]

[3]

[4]

[5]

Legal status

Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)^[1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I Illegal in Czech Republic and Latvia^[2]
Identifiers
IUPAC name 2-(2-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number	864445-43-2^Y
PubChem CID	44397540
ChemSpider	23256117^N
UNII	IP9911R8A0
ChEMBL	ChEMBL188031^N
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^N Key:FFLSJIQJQKDDCM-UHFFFAOYSA-N^N
^NY (what is this?) (verify)