Cannabis Ruderalis

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| CAS_number = 619294-62-1
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Revision as of 19:58, 10 April 2020

JWH-176
Legal status
Legal status
Identifiers
  • 1-([(1E)-3-Pentylinden-1-ylidine]methyl)naphthalene
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H24
Molar mass324.467 g·mol−1
3D model (JSmol)
  • CCCCCc(c3)c1ccccc1c3=Cc2cccc4ccccc24
  • 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-XLNRJJMWSA-N
  (verify)

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

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 23rd 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]

See also

References

  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
  5. ^ "The Misuse of Drugs Act 1971 (Amendment) Order 2009", legislation.gov.uk, The National Archives, SI 2009/3209
source: https://en.wikipedia.org/wiki/Special%3ADiff%2F950206795

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