JWH-122

JWH-122
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;
Identifiers
	IUPAC name (4-Methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone;
CAS Number	619294-47-2 ;
ChemSpider	24623066 ;
UNII	44147RI31X;
KEGG	C22796 ;
ChEMBL	ChEMBL557004 ;
CompTox Dashboard (EPA)	DTXSID00210965 ;
Chemical and physical data
Formula	C25H25NO
Molar mass	355.481 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(c4c3cccc4)C;
	InChI 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 ; Key:HUKJQMKQFWYIHS-UHFFFAOYSA-N ;
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JWH-122 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is a methylated analogue of JWH-018. It has a K_i 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]

^ 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.
^ 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.
^ "Tests Show Synthetic Drug Contaminated Holiday Bread from CA Bakery". Food Safety News. 2015-02-02.

[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.

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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
Identifiers
IUPAC name (4-Methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone
CAS Number	619294-47-2^N
ChemSpider	24623066^Y
UNII	44147RI31X
KEGG	C22796^Y
ChEMBL	ChEMBL557004^Y
CompTox Dashboard (EPA)	DTXSID00210965
Chemical and physical data
Formula	C₂₅H₂₅NO
Molar mass	355.481 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(c4c3cccc4)C
InChI 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^Y Key:HUKJQMKQFWYIHS-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)