JWH-176

JWH-176
JWH-176.svg
Legal status
Legal status
  • In general: legal
Identifiers
CAS Number
ChemSpider
Chemical and physical data
Formula C25H24
Molar mass 324.457 g/mol 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 only 26.0nM, 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, Dr. John W. Huffman.

Stereochemistry[edit]

JWH-171

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]

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.