WIN 55,212-2

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WIN 55,212-2
Legal status
Legal status
Identifiers
  • (11R)-2-Methyl-11-[(morpholin-4-yl)methyl]-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraene
JSmol)
  • CC1=C(C2=C3N1[C@@H](COC3=CC=C2)CN4CCOCC4)C(=O)C5=CC=CC6=CC=CC=C65
  • InChI=1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1 ☒N
  • Key:HQVHOQAKMCMIIM-HXUWFJFHSA-N ☒N
 ☒NcheckY (what is this?)  (verify)
Pancreatic stellate cells. The cells in the lower frame are under the action of WIN 55,212-2. They are thought to assume a more "quiescent" phenotype. From Michalski et al., 2008.[2]

WIN 55,212-2 is a chemical described as an aminoalkylindole derivative, which produces effects similar to those of cannabinoids such as tetrahydrocannabinol (THC) but has an entirely different chemical structure.[3][4][5]

WIN 55,212-2 is a potent cannabinoid

MAP kinase via receptor-mediated signaling.[9]

At 5 μM WIN 55,212-2 inhibits

CB1 receptor-dependent fashion.[10]

WIN 55,212-2, along with

markers. This anti-inflammatory action is induced through agonist action at cannabinoid receptors, which prevents microglial
activation that elicits the inflammation.

WIN 55,212-2 is a full agonist at the

CB1 cannabinoid receptor (Ki = 1.9 nM) and has much higher affinity than THC (Ki = 41 nM) for this receptor.[11] WIN 55,212-2 is also an agonist of the PPARα and PPARγ nuclear receptors.[12]

WIN 55,212-2 reduces voluntary wheel running in laboratory mice, but with effects that depend on both genetic background and sex.[13]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as WIN 55,212-2 are

Schedule I Controlled Substances.[14] WIN 55,212-2 is illegal in the UK.[15]

WIN 55,212-2 is also a

endothelial nitric oxide synthase (eNOS) cardiac equilibrium.[16][17]

See also

References

  1. ^ "Controlled Drugs and Substance Act - Schedule II". Justice Laws Website. Government of Canada. 18 March 2021.
  2. PMID 18301776
    .
  3. PMID 1335057
    .
  4. PMID 11459762
    .
  5. S2CID 10848076
    .
  6. PMID 7565624
    .
  7. S2CID 1619608
    .
  8. S2CID 33643599
    .
  9. PMID 8526880
    .
  10. PMID 21615727
    .
  11. PMID 8450470
    .
  12. PMID 27077495
    .
  13. S2CID 25174208
    .
  14. ^ 21 U.S.C. § 812: Schedules of controlled substances
  15. ^ "The Misuse of Drugs Act 1971 (Amendment) Order 2013". legislation.gov.uk.
  16. S2CID 32450365
    .
  17. S2CID 24074568
    .

Further reading

External links
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