JWH-307

JWH-307
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule I;
Identifiers
	IUPAC name (5-(2-Fluorophenyl)-1-pentylpyrrol-3-yl)-naphthalen-1-ylmethanone;
CAS Number	914458-26-7 ;
PubChem CID	16049783;
ChemSpider	13178178;
UNII	06QTR14ONW;
CompTox Dashboard (EPA)	DTXSID60581542 ;
Chemical and physical data
Formula	C26H24FNO
Molar mass	385.482 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1C=C(C=C1C2=CC=CC=C2F)C(=O)C3=CC=CC4=CC=CC=C43;
	InChI InChI=1S/C26H24FNO/c1-2-3-8-16-28-18-20(17-25(28)23-13-6-7-15-24(23)27)26(29)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3; Key:WYNZPDDTQGVCLZ-UHFFFAOYSA-N;
	(verify)

JWH-307 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors. It is somewhat selective for the CB₂ subtype, with a K_i of 7.7 nM at CB₁ vs 3.3 nM at CB₂.^[1] It was discovered by, and named after, John W. Huffman. JWH-307 was detected as an ingredient in synthetic cannabis smoking blends in 2012, initially in Germany.^[2]^[3]

In the United States, CB₁ receptor agonists of the 3-(1-naphthoyl)pyrrole class such as JWH-307 are Schedule I Controlled Substances.^[4]

References

^ Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB₁ and CB₂ receptors. Bioorganic & Medicinal Chemistry Letters 2006; 16:5432-5435.
^ Ernst L, Krüger K, Lindigkeit R, Schiebel HM, Beuerle T (October 2012). "Synthetic cannabinoids in "spice-like" herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market". Forensic Science International. 222 (1–3): 216–22. doi:10.1016/j.forsciint.2012.05.027. PMID 22748479.
^ Kneisel S, Auwärter V (July 2012). "Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction". Journal of Mass Spectrometry. 47 (7): 825–35. Bibcode:2012JMSp...47..825K. doi:10.1002/jms.3020. PMID 22791249.
^ 21 U.S.C. § 812: Schedules of controlled substances

[1] Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB₁ and CB₂ receptors. Bioorganic & Medicinal Chemistry Letters 2006; 16:5432-5435.

[2] Ernst L, Krüger K, Lindigkeit R, Schiebel HM, Beuerle T (October 2012). "Synthetic cannabinoids in "spice-like" herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market". Forensic Science International. 222 (1–3): 216–22. doi:10.1016/j.forsciint.2012.05.027. PMID 22748479.

[3] Kneisel S, Auwärter V (July 2012). "Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction". Journal of Mass Spectrometry. 47 (7): 825–35. Bibcode:2012JMSp...47..825K. doi:10.1002/jms.3020. PMID 22791249.

[4] 21 U.S.C. § 812: Schedules of controlled substances

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See also

References