WIN 55,212-2
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Systematic (IUPAC) name | |
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(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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Identifiers | |
CAS Number | 131543-23-2 |
PubChem | CID: 5311501 |
IUPHAR/BPS | 733 |
ChemSpider | 4470978 |
ChEBI | CHEBI:73295 |
ChEMBL | CHEMBL188 |
Chemical data | |
Formula | C27H26N2O3 |
Molecular 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.[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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
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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; Lua error in package.lua at line 80: module 'strict' not found.
- 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
- Pages with broken file links
- Chemical articles having calculated molecular weight overwritten
- Infobox drug articles without a structure image
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
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- Drugboxes with an unspecified ATC code
- Drugs with no legal status
- Articles with unsourced statements from December 2010
- Aminoalkylindoles
- Cannabinoids
- Morpholines
- Naphthoylindoles
- WIN compounds
- CB1 receptor agonists