JWH-368

JWH-368
Legal status
Legal status	CA: Schedule II; UK: Class B;
Identifiers
	IUPAC name [5-(3-Fluorophenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone;
CAS Number	914458-31-4 ;
PubChem CID	44418331;
ChemSpider	23277909 ;
UNII	HYS2YS4WNM;
CompTox Dashboard (EPA)	DTXSID60658824 ;
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=C2)F)C(=O)C3=CC=CC4=CC=CC=C43;
	InChI InChI=1S/C26H24FNO/c1-2-3-6-15-28-18-21(17-25(28)20-11-7-12-22(27)16-20)26(29)24-14-8-10-19-9-4-5-13-23(19)24/h4-5,7-14,16-18H,2-3,6,15H2,1H3 ; Key:OCOICOMCAJNSCA-UHFFFAOYSA-N ;

JWH-368 ([5-(3-Fluorophenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 16 ± 1nM) and CB₂ (K_i = 9.1 ± 0.7nM) receptors, binding ~1.76 times stronger to the CB₂ receptor than to the CB₁ receptor. JWH-368 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB₁ receptor.^[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.

[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.

[1]

Legal status

Legal status	CA: Schedule II UK: Class B
Identifiers
IUPAC name [5-(3-Fluorophenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone
CAS Number	914458-31-4^Y
PubChem CID	44418331
ChemSpider	23277909^Y
UNII	HYS2YS4WNM
CompTox Dashboard (EPA)	DTXSID60658824
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=C2)F)C(=O)C3=CC=CC4=CC=CC=C43
InChI InChI=1S/C26H24FNO/c1-2-3-6-15-28-18-21(17-25(28)20-11-7-12-22(27)16-20)26(29)24-14-8-10-19-9-4-5-13-23(19)24/h4-5,7-14,16-18H,2-3,6,15H2,1H3^Y Key:OCOICOMCAJNSCA-UHFFFAOYSA-N^Y