JWH-122

JWH-122
Legal status
Legal status	AU: S9 (Prohibited substance) ; 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;
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 ;
	(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 K_i of 0.69 nM at CB₁ and 1.2 nM at CB₂.[1]

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, CA that was laced with JWH-122.[2]

Legal status

Australia

JWH-122 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[3] 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.[3]

China

As of October 2015 JWH-122 is a controlled substance in China.[4]

United States

In the United States, JWH-122 is a Schedule I Controlled Substance.[5]

References

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.
"Poisons Standard". Federal Register of Legislation. The Australian Government. October 2015.
"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. Retrieved 1 October 2015.
"Controlled Substances" (PDF). Diversion Control Division. U.S. Department of Justice, Drug Enforcement Division (DEA).

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[1] 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.

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

[Poisons_Standard-3] "Poisons Standard". Federal Register of Legislation. The Australian Government. October 2015.

[4] "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. Retrieved 1 October 2015.

[5] "Controlled Substances" (PDF). Diversion Control Division. U.S. Department of Justice, Drug Enforcement Division (DEA).