JWH-146

Chemical compound
Identifiers
  • (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone
CAS Number
  • 914458-21-2 checkY
PubChem CID
  • 44418308
ChemSpider
  • 23277883 checkY
UNII
  • 5446SVK6LH
ChEMBL
  • ChEMBL219970 ☒N
Chemical and physical dataFormulaC28H29NOMolar mass395.546 g·mol−13D model (JSmol)
  • Interactive image
  • O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(CCCCCCC)C(C4=CC=CC=C4)=C3
InChI
  • InChI=1S/C28H29NO/c1-2-3-4-5-11-19-29-21-24(20-27(29)23-14-7-6-8-15-23)28(30)26-18-12-16-22-13-9-10-17-25(22)26/h6-10,12-18,20-21H,2-5,11,19H2,1H3 checkY
  • Key:JDBFNFBWXVCTSA-UHFFFAOYSA-N checkY

JWH-146 (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 21 ± 2nM) and CB2 (Ki = 62 ± 5nM) receptors, with a moderate (~2.9x) selectivity for the CB1 receptor over the CB2 receptor. JWH-146 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.[1]

Legality

In the United States JWH-146 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-146.[2][3][4][5]

In Canada, JWH-146 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.[citation needed]

In the United Kingdom, JWH-146 and other naphthoylpyrrole-based cannabinoids are considered Class B drugs under the Misuse of Drugs Act 1971.[citation needed]

See also

References

  1. ^ Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR (October 2006). "1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors". Bioorganic & Medicinal Chemistry Letters. 16 (20): 5432–5. doi:10.1016/j.bmcl.2006.07.051. PMID 16889960.
  2. ^ 21 U.S.C. § 812: Schedules of controlled substances
  3. ^ "The 2020 Florida Statutes". www.leg.state.fl.us. Retrieved 20 August 2021.
  4. ^ "Arizona Revised Statutes Title 13. Criminal Code § 13-3401". www.azleg.gov. Retrieved 20 August 2021.
  5. ^ "California Code, Health and Safety Code - HSC § 11357.5". Findlaw.
  • v
  • t
  • e
Phytocannabinoids
(comparison)
Cannabibutols
  • CBB
Cannabichromenes
Cannabicyclols
  • CBL
    • CBLA
  • CBLB
  • CBLP
    • CBLPA
  • CBLV
    • CBLVA
Cannabidiols
Cannabielsoins
  • CBE
    • CBEA
      • CBEA-A
      • CBEA-B
  • CBEB
  • CBEP
    • CBEPA
  • CBEV
Cannabigerols
  • CBG
    • CBGA
    • CBGB
    • CBGBA
    • CBGM
      • CBGAM
  • CBGP
    • CBGPA
  • CBNR
    • CBNRA
      • CBNRA-A
  • CBGV
    • CBGVA
      • CBGVA-A
  • CBGQ
Cannabiphorols
  • CBP
Cannabinols
  • CBN
    • CBNA
    • CBN-C1
    • CBN-C2
    • CBN-C4
    • CBNM
  • CBND
    • CBNDA
  • CBNP
    • CBNPA
  • CBVD
    • CBVDA
Cannabitriols
  • CBT
    • CBTA
  • CBTB
  • CBTV
    • CBTVA
  • CBTP
    • CBTPA
Cannabivarins
Delta-8-tetrahydrocannabinols
  • Delta-8-THC
    • Delta-8-THCA
      • Delta-8-THCA-A
  • Delta-8-THCB
  • Delta-8-THCP
  • Delta-8-THCV
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
EndocannabinoidsSynthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Hydrocarbons
Indazole carboxamides
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Pyrrolobenzoxazines
Quinolinyl esters
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Tetramethylcyclo-
propylindoles
Others
Allosteric CBRTooltip Cannabinoid receptor ligandsEndocannabinoid
enhancers
(inactivation inhibitors)Anticannabinoids
(antagonists/inverse
agonists/antibodies)


Stub icon

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e