JWH-193

JWH-193
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-methylnaphthalen-1-ylmethanone;
CAS Number	133438-58-1 ;
PubChem CID	10250276;
ChemSpider	8425762;
UNII	WB1TIJ1IO9;
CompTox Dashboard (EPA)	DTXSID70158108 ;
Chemical and physical data
Formula	C26H26N2O2
Molar mass	398.506 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3cccc1c3c(ccc1C)C(=O)c5c2ccccc2n(c5)CCN4CCOCC4;
	InChI InChI=1S/C26H26N2O2/c1-19-10-11-23(21-7-3-2-6-20(19)21)26(29)24-18-28(25-9-5-4-8-22(24)25)13-12-27-14-16-30-17-15-27/h2-11,18H,12-17H2,1H3; Key:ICKWPPYMDARCKJ-UHFFFAOYSA-N;
	(verify)

JWH-193 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-193 has a binding affinity at the CB₁ receptor of 6 nM, binding around seven times more tightly than the parent compound JWH-200,^[1] though with closer to twice the potency of JWH-200 in activity tests.

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-193 are Schedule I Controlled Substances.^[2]

Related compounds

A structural isomer of JWH-193 with the methyl group on the indole ring instead of the naphthoyl ring, was also found to be of similarly increased potency over JWH-200.^[3]^[4]

6-Methyl-JWH-200

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.
^ 21 U.S.C. § 812: Schedules of controlled substances
^ Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, et al. (August 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 (November 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.

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[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.

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

[pmid7636873-3] Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, et al. (August 1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. doi:10.1021/jm00016a013. PMID 7636873.

[pmid9804691-4] Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (November 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.

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[2]

[3]

[4]

JWH-193

Related compounds

See also

References

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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-methylnaphthalen-1-ylmethanone
CAS Number	133438-58-1^Y
PubChem CID	10250276
ChemSpider	8425762
UNII	WB1TIJ1IO9
CompTox Dashboard (EPA)	DTXSID70158108
Chemical and physical data
Formula	C₂₆H₂₆N₂O₂
Molar mass	398.506 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c3cccc1c3c(ccc1C)C(=O)c5c2ccccc2n(c5)CCN4CCOCC4
InChI InChI=1S/C26H26N2O2/c1-19-10-11-23(21-7-3-2-6-20(19)21)26(29)24-18-28(25-9-5-4-8-22(24)25)13-12-27-14-16-30-17-15-27/h2-11,18H,12-17H2,1H3 Key:ICKWPPYMDARCKJ-UHFFFAOYSA-N
(verify)