JWH-175

JWH-175
Legal status
Legal status	AU: Illegal; UK: Illegal; US: Schedule I; Illegal in Russia;
Identifiers
	IUPAC name (1-Pentylindol-3-yl)naphthalen-1-ylmethane;
CAS Number	619294-35-8 ;
PubChem CID	56603534;
ChemSpider	29341789 ;
UNII	3S82KAS832;
CompTox Dashboard (EPA)	DTXSID90717796 ;
Chemical and physical data
Formula	C24H25N
Molar mass	327.471 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3cccc2c3cccc2Cc(cn4CCCCC)c1ccccc14;
	InChI InChI=1S/C24H25N/c1-2-3-8-16-25-18-21(23-14-6-7-15-24(23)25)17-20-12-9-11-19-10-4-5-13-22(19)20/h4-7,9-15,18H,2-3,8,16-17H2,1H3 ; Key:TYBRSILIYTUTSQ-UHFFFAOYSA-N ;
	(what is this?)

JWH-175 is a drug from the naphthylmethylindole family which acts as a cannabinoid receptor agonist. It was invented by the scientist John W. Huffman and colleagues at Clemson University. JWH-175 is closely related to the widely used cannabinoid designer drug JWH-018, but with the ketone bridge replaced by a simpler methylene bridge. It is several times weaker than JWH-018, having a binding affinity at the CB₁ receptor of 22 nM, though some derivatives substituted at the 4-position of the naphthyl ring have potency more closely approaching that of the equivalent naphthoylindoles.^[1] This makes JWH-175 considerably less potent than most synthetic cannabinoid drugs used in synthetic cannabis blends, and it is unclear if JWH-175 has ever been used for this purpose. However it has still been explicitly banned in several jurisdictions including Russia and some Australian states, in order to stop its potential use as an ingredient in such products. In the United States, all CB₁ receptor agonists of the 3-(1-naphthylmethane)indole class such as JWH-175 are Schedule I Controlled Substances.^[2]

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

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[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

[1]

[2]

Legal status

Legal status	AU: Illegal UK: Illegal US: Schedule I Illegal in Russia
Identifiers
IUPAC name (1-Pentylindol-3-yl)naphthalen-1-ylmethane
CAS Number	619294-35-8^Y
PubChem CID	56603534
ChemSpider	29341789^N
UNII	3S82KAS832
CompTox Dashboard (EPA)	DTXSID90717796
Chemical and physical data
Formula	C₂₄H₂₅N
Molar mass	327.471 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c3cccc2c3cccc2Cc(cn4CCCCC)c1ccccc14
InChI InChI=1S/C24H25N/c1-2-3-8-16-25-18-21(23-14-6-7-15-24(23)25)17-20-12-9-11-19-10-4-5-13-22(19)20/h4-7,9-15,18H,2-3,8,16-17H2,1H3^N Key:TYBRSILIYTUTSQ-UHFFFAOYSA-N^N
^NY (what is this?)

JWH-175

See also

References