Jwh-176

JWH-176
Legal status
Legal status	UK: Class B ; US: Schedule I ;
Identifiers
	IUPAC name 1-([(1E)-3-Pentylinden-1-ylidine]methyl)naphthalene;
CAS Number	619294-62-1 ;
ChemSpider	29341653;
UNII	VA60GT97BB;
Chemical and physical data
Formula	C25H24
Molar mass	324.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=C\C(=C/c2cccc3ccccc32)c2ccccc21;
	InChI InChI=1S/C25H24/c1-2-3-4-11-21-18-22(25-16-8-7-15-24(21)25)17-20-13-9-12-19-10-5-6-14-23(19)20/h5-10,12-18H,2-4,11H2,1H3/b22-17+; Key:FPESBQVTVSBBSE-OQKWZONESA-N;
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Short description: Chemical compound

JWH-176 is an analgesic drug which acts as a cannabinoid receptor agonist. Its binding affinity at the CB₁ receptor is 26.0 nM, making it more potent than THC itself,^[1] however JWH-176 is particularly notable in that it is a hydrocarbon containing no heteroatoms. This demonstrates that reasonably high-affinity cannabinoid binding and agonist effects can be produced by compounds with no hydrogen bonding capacity at all, relying merely on Van der Waals and possibly hydrophobic interactions to bind to the receptor.^[2] It was discovered by, and named after, John W. Huffman.

Stereochemistry

JWH-176 is the (E)-stereoisomer of 1-([3-pentylinden-1-ylidine]methyl)naphthalene, whereas JWH-171 is the mixture of the (E)- and (Z)-isomers.^[3]

JWH-171

Legal status

In the United States, CB₁ receptor agonists of the 1-(1-naphthylmethylene)indene class such as JWH-176 and JWH-171 are Schedule I Controlled Substances.^[4]

As of 23 December 2009, any compound structurally derived from 1–(1–naphthylmethyl)indene by substitution at the 3–position of the indene ring by an alkyl group is a Class B drug in the United Kingdom.^[5]

References

↑ "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry 12 (12): 1395–411. 2005. doi:10.2174/0929867054020864. PMID 15974991.
↑ "Cannabinoids". Handbook of Experimental Pharmacology. 168. Springer. pp. 269. ISBN 3-540-22565-X.
↑ "Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes". Frontiers in Medicinal Chemistry. 4. 2010-12-10. pp. 661–687 (681). doi:10.2174/978160805207310904010661. ISBN 978-1-60805-346-9. https://books.google.com/books?id=N_luK703FKEC.
↑ 21 U.S.C. § 812: Schedules of controlled substances
↑ The Misuse of Drugs Act 1971 (Amendment) Order 2009, The National Archives, SI 2009/3209, http://legislation.gov.uk/uksi/2009/3209/made

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

[2] "Cannabinoids". Handbook of Experimental Pharmacology. 168. Springer. pp. 269. ISBN 3-540-22565-X.

[3] "Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes". Frontiers in Medicinal Chemistry. 4. 2010-12-10. pp. 661–687 (681). doi:10.2174/978160805207310904010661. ISBN 978-1-60805-346-9. https://books.google.com/books?id=N_luK703FKEC.

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

[5] The Misuse of Drugs Act 1971 (Amendment) Order 2009, The National Archives, SI 2009/3209, http://legislation.gov.uk/uksi/2009/3209/made

Jwh-176

Contents

Stereochemistry

Legal status

See also

References

Legal status

Legal status	UK: Class B US: Schedule I
Identifiers
IUPAC name 1-([(1E)-3-Pentylinden-1-ylidine]methyl)naphthalene
CAS Number	619294-62-1^Y
ChemSpider	29341653
UNII	VA60GT97BB
Chemical and physical data
Formula	C₂₅H₂₄
Molar mass	324.467 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=C\C(=C/c2cccc3ccccc32)c2ccccc21
InChI InChI=1S/C25H24/c1-2-3-4-11-21-18-22(25-16-8-7-15-24(21)25)17-20-13-9-12-19-10-5-6-14-23(19)20/h5-10,12-18H,2-4,11H2,1H3/b22-17+ Key:FPESBQVTVSBBSE-OQKWZONESA-N
(verify)