WIN 55,212-2
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| Systematic (IUPAC) name | |
| (R)-(+)-[2,3-Dihydro-5-methyl- 3-(4-morpholinylmethyl)pyrrolo [1,2,3-de]-1,4-benzoxazin-6-yl]- 1-napthalenylmethanone |
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| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 131543-23-2  |
| ATC code | ? |
| PubChem | CID 5311501 |
| IUPHAR ligand | 733 |
| ChemSpider | 4470978  |
| ChEBI | CHEBI:73295 |
| ChEMBL | CHEMBL188 |
| Chemical data | |
| Formula | C27H26N2O3 |
| Mol. mass | 426.52 g/mol |
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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.[1][2][3]
WIN 55,212-2 is a potent cannabinoid receptor agonist[4] that has been found to be a potent analgesic[5] in a rat model of neuropathic pain.[6] It activates p42 and p44 MAP kinase via receptor-mediated signaling.[7]
At 5 µM WIN 55,212-2 inhibit ATP production in sperm in a CB1 receptor-dependent fashion.[8]
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.[9]
WIN 55,212-2 reduces voluntary wheel running in laboratory mice, but with effects that depend on both genetic background and sex.[10]
External links [edit]
- Biomol 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
See also [edit]
References [edit]
- ^ 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.
- ^ Ferraro L, et al. The Cannabinoid Receptor Agonist WIN 55,212-2 Regulates Glutamate Transmission in Rat Cerebral Cortex: an In Vitro and In Vivo Study. Cerebral Cortex. 2001; (11):728-733.
- ^ Zhang, Q., et al. (2002). "In vitro metabolism of R(+)-2,3-dihydro-5-methyl-3-(morpholinyl)methylpyrrolo 1,2,3-de1,4-benzoxazinyl-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist". Drug metabolism and disposition: the biological fate of chemicals 30 (10): 1077–1086. doi:10.1124/dmd.30.10.1077. PMID 12228183.
- ^ C.C. Felder et al. Mol. Pharmacol. 1995 48 443
- ^ I.D. Meng et al. Nature 1998 395 381
- ^ U. Herzberg et al. Neurosci. Lett. 1997 221 157
- ^ M. Bouaboula et al. Biochem. J. 1995 312 637
- ^ Morgan, D. J., et al. (2012). "Δ9-Tetrahydrocannabinol (Δ9-THC) attenuates mouse sperm motility and male fecundity". British Journal of Pharmacology 165 (8): 2575–2583. doi:10.1111/j.1476-5381.2011.01506.x. PMC 3423255. PMID 21615727.
- ^ 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.
- ^ Keeney BK, et al. (2012). "Sex differences in cannabinoid receptor-1 (CB1) pharmacology in mice selectively bred for high voluntary wheel-running behavior". Pharmacology, Biochemistry and Behavior 101: 528–537. doi:10.1016/j.pbb.2012.02.017.
- ^ Michalski, C., et al. (2008). "Cannabinoids Reduce Markers of Inflammation and Fibrosis in Pancreatic Stellate Cells". In Gluud, Christian. PLoS ONE 3 (2): e1701. Bibcode:2008PLoSO...3.1701M. doi:10.1371/journal.pone.0001701. PMC 2253501. PMID 18301776.
