JWH-145

JWH-145
Legal status
Legal status	CA: Schedule II; UK: Class B;
Identifiers
	IUPAC name 1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone;
CAS Number	914458-19-8 ;
PubChem CID	44418304;
ChemSpider	23277878 ;
UNII	JRT5F2Y0NA;
ChEMBL	ChEMBL385940 ;
CompTox Dashboard (EPA)	DTXSID401016339 ;
Chemical and physical data
Formula	C26H25NO
Molar mass	367.492 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(C1=CN(CCCCC)C(C2=CC=CC=C2)=C1)C3=C(C=CC=C4)C4=CC=C3;
	InChI InChI=1S/C26H25NO/c1-2-3-9-17-27-19-22(18-25(27)21-12-5-4-6-13-21)26(28)24-16-10-14-20-11-7-8-15-23(20)24/h4-8,10-16,18-19H,2-3,9,17H2,1H3 ; Key:JLXYYSHMURZHKI-UHFFFAOYSA-N ;

JWH-145 (1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 14 ± 2nM) and CB₂ (K_i = 6.4 ± 0.4nM) receptors, with a moderate (~2.2x) selectivity for the CB₂ receptor. JWH-145 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 1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone
CAS Number	914458-19-8^Y
PubChem CID	44418304
ChemSpider	23277878^Y
UNII	JRT5F2Y0NA
ChEMBL	ChEMBL385940^Y
CompTox Dashboard (EPA)	DTXSID401016339
Chemical and physical data
Formula	C₂₆H₂₅NO
Molar mass	367.492 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(C1=CN(CCCCC)C(C2=CC=CC=C2)=C1)C3=C(C=CC=C4)C4=CC=C3
InChI InChI=1S/C26H25NO/c1-2-3-9-17-27-19-22(18-25(27)21-12-5-4-6-13-21)26(28)24-16-10-14-20-11-7-8-15-23(20)24/h4-8,10-16,18-19H,2-3,9,17H2,1H3^Y Key:JLXYYSHMURZHKI-UHFFFAOYSA-N^Y