WIN 55,212-2
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Formula | C27H26N2O3 |
Molar mass | 426.52 g/mol g·mol−1 |
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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.[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]
See also
References
- ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 18301776, please use {{cite journal}} with
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instead. - ^ 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.
- ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1093/cercor/11.8.728, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
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instead. - ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/S0304-3940(96)13308-5, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
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instead. - ^ 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.
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External links
- 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; PMID 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