JWH-176: Difference between revisions

'''JWH-~~171~~''' is an [[analgesic]] drug which acts as a [[cannabinoid receptor agonist]]. Its [[Dissociation constant#Protein-ligand binding|binding affinity]] at the CB1 receptor is ~~only 51~~.~~0nM~~, making it ~~slightly less~~ potent than [[THC]] itself,<ref>Huffman JW, Padgett LW. Recent ~~Developments~~ in the ~~Medicinal~~ ~~Chemistry~~ of ~~Cannabimimetic~~ ~~Indoles~~, ~~Pyrroles~~ and ~~Indenes.~~ ''Current Medicinal Chemistry~~'',~~ ~~2005;~~ 12: ~~1395-1411~~.</ref> however JWH-~~171~~ is particularly notable in that it is a [[hydrocarbon]] containing no [[heteroatom]]s. 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 force|Van der Waals]] interactions to bind to the receptor.<ref>~~Roger~~ Pertwee. Cannabinoids. Handbook of Experimental Pharmacology ~~Volume~~ 168, p 269. Springer. ~~ISBN~~ 3-540-22565-X</ref> It was discovered by, and named after, ~~Dr.~~ [[John W. Huffman]].

'''JWH-176''' is an [[analgesic]] drug which acts as a [[cannabinoid receptor agonist]]. Its [[Dissociation constant#Protein-ligand binding|binding affinity]] at the CB1 receptor is 26.0 nM, making it more potent than [[THC]] itself,<ref name="pmid15974991">{{cite journal | vauthors = Huffman JW, Padgett LW | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | journal = Current Medicinal Chemistry | volume = 12 | issue = 12 | pages = 1395–411 | date = 2005 | pmid = 15974991 | doi = 10.2174/0929867054020864 }}</ref> however JWH-176 is particularly notable in that it is a [[hydrocarbon]] containing no [[heteroatom]]s. 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 force|Van der Waals]] and possibly hydrophobic interactions to bind to the receptor.<ref>{{cite book | vauthors = Pertwee RG | title = Cannabinoids | series = Handbook of Experimental Pharmacology | volume = 168 | pages = 269 | publisher = Springer | isbn = 3-540-22565-X }}</ref> 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.<ref>{{cite book | vauthors = Huffman JW, Padgett LW | chapter = Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes |url=https://books.google.com/books?id=N_luK703FKEC|title=Frontiers in Medicinal Chemistry | volume = 4 | veditors = Rahman A, Iqbal Choudhary M, Reitz AB |date=2010-12-10|pages = 661–687 (681) |isbn = 978-1-60805-346-9 | doi = 10.2174/978160805207310904010661 }}</ref>

:[[File:JWH-171.svg|95px|thumb|left|JWH-171]]{{clear-left}}

==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 Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>

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.<ref>{{ Cite legislation UK | type = si | si = The Misuse of Drugs Act 1971 (Amendment) Order 2009 | year = 2009 | number = 3209 }}</ref>

==See also==

* [[JWH-175]]

==References==

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[[Category:Cannabinoids]]

[[Category:JWH cannabinoids]]

[[Category:~~Naphthalenes~~]]

[[Category:1-Naphthyl compounds]]

[[Category:Indenes]]

[[Category:Polycyclic aromatic hydrocarbons]]

[[Category:CB1 receptor agonists]]