JWH-309

JWH-309
Legal status
Legal status	CA: Schedule II; UK: Class B;
Identifiers
	IUPAC name naphthalen-1-yl-(5-naphthalen-1-yl-1-pentylpyrrol-3-yl)methanone;
CAS Number	914458-42-7 ;
PubChem CID	44418371;
ChemSpider	ID23277951 ;
UNII	5LC7L6AM73;
CompTox Dashboard (EPA)	DTXSID201016890 ;
Chemical and physical data
Formula	C30H27NO
Molar mass	417.552 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1C=C(C=C1C2=CC=CC3=CC=CC=C32)C(=O)C4=CC=CC5=CC=CC=C54;
	InChI InChI=1S/C30H27NO/c1-2-3-8-19-31-21-24(30(32)28-18-10-14-23-12-5-7-16-26(23)28)20-29(31)27-17-9-13-22-11-4-6-15-25(22)27/h4-7,9-18,20-21H,2-3,8,19H2,1H3 ; Key:WVISOUYKTUUDFW-UHFFFAOYSA-N ;

JWH-309 (naphthalen-1-yl-(5-naphthalen-1-yl-1-pentylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 41 ± 3nM) and CB₂ (K_i = 49 ± 7nM) receptors, displaying a slight selectivity for the former. JWH-309 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB₁ receptor.^[1]

Legality

In the United States JWH-309 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-309.^[2]^[3]^[4]^[5]

In Canada, JWH-309 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-309 and other naphthoylpyrrole-based cannabinoids are considered Class B drugs under the Misuse of Drugs Act 1971.

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-(5-naphthalen-1-yl-1-pentylpyrrol-3-yl)methanone
CAS Number	914458-42-7^Y
PubChem CID	44418371
ChemSpider	ID23277951^Y
UNII	5LC7L6AM73
CompTox Dashboard (EPA)	DTXSID201016890
Chemical and physical data
Formula	C₃₀H₂₇NO
Molar mass	417.552 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCN1C=C(C=C1C2=CC=CC3=CC=CC=C32)C(=O)C4=CC=CC5=CC=CC=C54
InChI InChI=1S/C30H27NO/c1-2-3-8-19-31-21-24(30(32)28-18-10-14-23-12-5-7-16-26(23)28)20-29(31)27-17-9-13-22-11-4-6-15-25(22)27/h4-7,9-18,20-21H,2-3,8,19H2,1H3^Y Key:WVISOUYKTUUDFW-UHFFFAOYSA-N^Y

JWH-309

Legality

See also

References