WIN 55,212-2

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WIN 55,212-2
200px
Systematic (IUPAC) name
(R)-(+)-[2,3-Dihydro-5-methyl-
3-(4-morpholinylmethyl)pyrrolo
[1,2,3-de]-1,4-benzoxazin-6-yl]-
1-napthalenylmethanone
Identifiers
CAS Number 131543-23-2 YesY
PubChem CID: 5311501
IUPHAR/BPS 733
ChemSpider 4470978 N
ChEBI CHEBI:73295 N
ChEMBL CHEMBL188 N
Chemical data
Formula C27H26N2O3
Molecular mass 426.52 g/mol
 NYesY (what is this?)  (verify)
File:Pancreatic stellate cell cropped.png
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.[1]

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.[2][3][4]

WIN 55,212-2 is a potent cannabinoid receptor agonist[5] that has been found to be a potent analgesic[6] in a rat model of neuropathic pain.[7] It activates p42 and p44 MAP kinase via receptor-mediated signaling.[8]

At 5 µM WIN 55,212-2 inhibit ATP production in sperm in a CB1 receptor-dependent fashion.[9]

WIN 55,212-2, along with HU-210 and JWH-133, may prevent the inflammation caused by amyloid beta proteins involved in Alzheimer's disease, in addition to preventing cognitive impairment and loss of neuronal markers. This anti-inflammatory action is induced through agonist action at cannabinoid receptors, which prevents microglial activation that elicits the inflammation. Additionally, cannabinoids completely abolish neurotoxicity related to microglial activation in rat models.[citation needed]

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.[10]

WIN 55,212-2 reduces voluntary wheel running in laboratory mice, but with effects that depend on both genetic background and sex.[11]

WIN 55,212-2 is illegal in the UK[12]

See also

References

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  2. Compton DR, et al. Aminoalkylindole Analogs: Cannabimimetic Activity of a Class of Compounds Structurally Distinct from Δ9-Tetrahydrocannabinol. Journal of Pharmacology and Experimental Therapeutics. 1992; 263(3):1118-1126.
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  5. Felder, C. C.; Joyce, K. E.; Briley, E. M.; Mansouri, J.; MacKie, K.; Blond, O.; Lai, Y.; Ma, A. L.; Mitchell, R. L. (1995). "Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors". Molecular pharmacology. 48 (3): 443–450. PMID 7565624.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  10. Kuster, J. E.; et al. (1993). "Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids". The Journal of Pharmacology and Experimental Therapeutics. 264 (3): 1352–1363. PMID 8450470.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  12. "The Misuse of Drugs Act 1971 (Amendment) Order 2013".<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>

External links

  • Enzo Life Sciences Win 55,212-2 Data Sheet
  • The cannabinoid WIN 55,212-2 inhibits transient receptor potential vanilloid 1 (TRPV1) and evokes peripheral antihyperalgesia via calcineurin. 2006 Jul 18; PubMed 16849427
  • JNeurosci.org Prevention of Alzheimer's Disease Pathology by Cannabinoids: Neuroprotection Mediated by Blockade of Microglial Activation
  • New Scientist: Hope for cannabis-based drug for Alzheimer's