JWH-116

JWH-116
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (2-Ethyl-1-pentyl-1H-indol-3-yl)-1-naphthalenylmethanone;
CAS Number	619294-64-3;
ChemSpider	29341485;
UNII	RKP962UAI3;
CompTox Dashboard (EPA)	DTXSID60210966 ;
Chemical and physical data
Formula	C26H27NO
Molar mass	369.508 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1C2=CC=CC=C2C(=C1CC)C(=O)C3=CC=CC4=CC=CC=C43;
	InChI InChI=1S/C26H27NO/c1-3-5-10-18-27-23(4-2)25(22-15-8-9-17-24(22)27)26(28)21-16-11-13-19-12-6-7-14-20(19)21/h6-9,11-17H,3-5,10,18H2,1-2H3; Key:AQHPTHKEKSWGPO-UHFFFAOYSA-N;

JWH-116 is a synthetic cannabinoid receptor ligand from the naphthoylindole family. It is the indole 2-ethyl derivative of related compound JWH-018. The binding affinity of JWH-116 for the CB₁ receptor is reported as K_i = 52 ± 5 nM.^[1]

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-116 are Schedule I Controlled Substances.^[2]

References

^ Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, et al. (February 2003). "3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor". Bioorganic & Medicinal Chemistry. 11 (4): 539–49. doi:10.1016/s0968-0896(02)00451-0. PMID 12538019. S2CID 29107765.
^ 21 U.S.C. § 812: Schedules of controlled substances

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[Huffman_2003-1] Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, et al. (February 2003). "3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor". Bioorganic & Medicinal Chemistry. 11 (4): 539–49. doi:10.1016/s0968-0896(02)00451-0. PMID 12538019. S2CID 29107765.

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

[1]

[2]

Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B US: Schedule I
Identifiers
IUPAC name (2-Ethyl-1-pentyl-1H-indol-3-yl)-1-naphthalenylmethanone
CAS Number	619294-64-3
ChemSpider	29341485
UNII	RKP962UAI3
CompTox Dashboard (EPA)	DTXSID60210966
Chemical and physical data
Formula	C₂₆H₂₇NO
Molar mass	369.508 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCN1C2=CC=CC=C2C(=C1CC)C(=O)C3=CC=CC4=CC=CC=C43
InChI InChI=1S/C26H27NO/c1-3-5-10-18-27-23(4-2)25(22-15-8-9-17-24(22)27)26(28)21-16-11-13-19-12-6-7-14-20(19)21/h6-9,11-17H,3-5,10,18H2,1-2H3 Key:AQHPTHKEKSWGPO-UHFFFAOYSA-N

JWH-116

See also

References