JWH-372

JWH-372
Legal status
Legal status	CA: Schedule II; UK: Class B;
Identifiers
	IUPAC name naphthalen-1-yl-[1-pentyl-5-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methanone;
CAS Number	914458-28-9 ;
PubChem CID	44418325;
ChemSpider	23277903 ;
CompTox Dashboard (EPA)	DTXSID401337000 ;
Chemical and physical data
Formula	C27H24F3NO
Molar mass	435.490 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1C=C(C=C1C2=CC=CC=C2C(F)(F)F)C(=O)C3=CC=CC4=CC=CC=C43;
	InChI InChI=1S/C27H24F3NO/c1-2-3-8-16-31-18-20(17-25(31)23-13-6-7-15-24(23)27(28,29)30)26(32)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3 ; Key:CYPUIQJYGVOHMM-UHFFFAOYSA-N ;

JWH-372 (naphthalen-1-yl-[1-pentyl-5-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as a potent and selective agonist of the CB₂ receptor. JWH-372 binds approximately 9 times stronger to the CB₂ receptor (K_i = 8.2 ± 0.2nM) than the CB₁ receptor (K_i = 77 ± 2nM). The selectivity of JWH-372 for the CB₂ receptor is likely due to the electron-withdrawing character of the trifluoromethyl group rather than steric effects, as the o-methyl compound JWH-370 was only mildly selective for the CB₂ receptor (CB₁ K_i = 5.6 ± 0.4nM, CB₂ K_i = 4.0 ± 0.5nM). ^[1]

Legality

In the United States JWH-372 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-372.^[2]^[3]^[4]^[5]

In Canada, JWH-372 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.^{[citation needed]}

In the United Kingdom, JWH-372 and other naphthoylpyrrole-based cannabinoids are considered Class B drugs under the Misuse of Drugs Act 1971.^{[citation needed]}

References

^ Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR (October 2006). "1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors". Bioorganic & Medicinal Chemistry Letters. 16 (20): 5432–5. doi:10.1016/j.bmcl.2006.07.051. PMID 16889960.
^ 21 U.S.C. § 812: Schedules of controlled substances
^ "The 2020 Florida Statutes". www.leg.state.fl.us. Retrieved 20 August 2021.
^ "Arizona Revised Statutes Title 13. Criminal Code § 13-3401". www.azleg.gov. Retrieved 20 August 2021.
^ "California Code, Health and Safety Code - HSC § 11357.5". Findlaw.

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[1] Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR (October 2006). "1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors". Bioorganic & Medicinal Chemistry Letters. 16 (20): 5432–5. doi:10.1016/j.bmcl.2006.07.051. PMID 16889960.

[2] 21 U.S.C. § 812: Schedules of controlled substances

[3] "The 2020 Florida Statutes". www.leg.state.fl.us. Retrieved 20 August 2021.

[4] "Arizona Revised Statutes Title 13. Criminal Code § 13-3401". www.azleg.gov. Retrieved 20 August 2021.

[5] "California Code, Health and Safety Code - HSC § 11357.5". Findlaw.

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Legal status

Legal status	CA: Schedule II UK: Class B
Identifiers
IUPAC name naphthalen-1-yl-[1-pentyl-5-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methanone
CAS Number	914458-28-9^Y
PubChem CID	44418325
ChemSpider	23277903^Y
CompTox Dashboard (EPA)	DTXSID401337000
Chemical and physical data
Formula	C₂₇H₂₄F₃NO
Molar mass	435.490 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCN1C=C(C=C1C2=CC=CC=C2C(F)(F)F)C(=O)C3=CC=CC4=CC=CC=C43
InChI InChI=1S/C27H24F3NO/c1-2-3-8-16-31-18-20(17-25(31)23-13-6-7-15-24(23)27(28,29)30)26(32)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3^Y Key:CYPUIQJYGVOHMM-UHFFFAOYSA-N^Y

JWH-372

Legality

See also

References