JWH-176

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  (Redirected from JWH-171)
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JWH-176
JWH-176.svg
Legal status
Legal status
Identifiers
CAS Number
ChemSpider
Chemical and physical data
FormulaC25H24
Molar mass324.467 g·mol−1
3D model (JSmol)
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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 interactions to bind to the receptor.[2] It was discovered by, and named after, John W. Huffman.

Stereochemistry[edit]

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[edit]

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]

See also[edit]

References[edit]

  1. ^ Huffman JW, Padgett LW. Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes. Current Medicinal Chemistry, 2005; 12: 1395-1411.
  2. ^ Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. ISBN 3-540-22565-X
  3. ^ Rahman, Atta-ur; Iqbal Choudhary, M; Reitz, Allen B (2010-12-10). Frontiers in Medicinal Chemistry , Volume (4). p. 681. ISBN 978-1608052073.
  4. ^ 21 U.S.C. § 812: Schedules of controlled substances