JWH-198

JWH-198
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone;
CAS Number	166599-76-4 ;
PubChem CID	10319620;
ChemSpider	8495084 ;
UNII	J53IGM38PB;
CompTox Dashboard (EPA)	DTXSID40168133 ;
Chemical and physical data
Formula	C26H26N2O3
Molar mass	414.505 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3;
	InChI InChI=1S/C26H26N2O3/c1-30-25-11-10-22(19-6-2-3-8-21(19)25)26(29)23-18-28(24-9-5-4-7-20(23)24)13-12-27-14-16-31-17-15-27/h2-11,18H,12-17H2,1H3 ; Key:QWHSUXWDDKWTOG-UHFFFAOYSA-N ;
	(what is this?) (verify)

JWH-198 is a drug from the aminoalkylindole and naphthoylindole families which acts as a cannabinoid receptor agonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a binding affinity at the CB₁ receptor of 10 nM, binding around four times more tightly than the parent compound JWH-200, which has no substitution on the naphthoyl ring.^[1] It has been used mainly in molecular modelling of the cannabinoid receptors.^[2]^[3]

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-198 are Schedule I Controlled Substances.^[4]

References

^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
^ Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM (Aug 1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. doi:10.1021/jm00016a013. PMID 7636873.
^ Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (Nov 1998). "Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis". Journal of Medicinal Chemistry. 41 (23): 4521–32. doi:10.1021/jm980305c. PMID 9804691.
^ 21 U.S.C. § 812: Schedules of controlled substances

[pmid15974991-1] Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.

[pmid7636873-2] Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM (Aug 1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. doi:10.1021/jm00016a013. PMID 7636873.

[pmid9804691-3] Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (Nov 1998). "Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis". Journal of Medicinal Chemistry. 41 (23): 4521–32. doi:10.1021/jm980305c. PMID 9804691.

[4] 21 U.S.C. § 812: Schedules of controlled substances

[1]

[2]

[3]

[4]

See also

References