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WIN 55,212-2



WIN 55,212-2
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
ATC code  ?
PubChem 5311501
Chemical data
Formula C27H26N2O3 
Mol. mass 522.61 g/mol
SMILES search in eMolecules, PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

WIN 55,212-2 is a drug described as an aminoalkylindole derivative, that produces effects similar to those of Cannabinoid derivatives such as THC but has an entirely different chemical structure.[1][2][3]

WIN 55,212-2 is a potent cannabinoid receptor agonist [4] which 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].

WIN55,212-2, along side HU-210 and JWH-133, are implicated in preventing the inflammation caused by Amyloid beta proteins involved in Alzheimer's Disease, in addition to preventing cognitive impairment and loss of neuronal markers. This antiinflamatory action is induced through the agonization of cannabinoid receptors which prevents microglial activation that elicits the inflammation. Additionally, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.

WIN55212-2 is a weaker partial agonist than THC, but with higher affinity to the CB1 receptor. [8] This means that the threshold dose for onset of effects is smaller than that of THC, but the maximum effects attainable are not as strong as those of THC, meaning that WIN55212-2 could potentially be used as a legal cannabis substitute drug, for instance as an alternative to medical marijuana. WIN55212-2 produces cannabis-like effects in humans within the oral dosage range of 1 to 3 miligrams however the effects are described as milder and shorter lasting when compared to THC[citation needed].

References

  1. ^ Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR. 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.
  2. ^ Ferraro L, Tomasini MC, Gessa GL, Bebe BW, Tanganelli S, Antonelli T. 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.
  3. ^ Zhang Q, Ma P, Iszard M, Cole RB, Wang W, Wang G. In Vitro Metabolism of R(+)-[2,3-Dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a Cannabinoid Receptor Agonist. Drug Metabolism and Disposition. 2002; 30(10):1077-1086.
  4. ^ C.C. Felder et al. Mol. Pharmacol. 1995 48 443
  5. ^ I.D. Meng et al. Nature 1998 395 381
  6. ^ U. Herzberg et al. Neurosci. Lett. 1997 221 157
  7. ^ M. Bouaboula et al. Biochem. J. 1995 312 637
  8. ^ Kuster JE, Stevenson JI, Ward SJ, D'Ambra TE, Haycock DA. Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids. Journal of Pharmacology and Experimental Therapeutics. 1993 Mar;264(3):1352-63.
v • d • e
Cannabinoids
Plant cannabinoidsCBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • 11-Hydroxy-THC • THCV
Synthetic cannabinoidsAjulemic acid • AM251 • CP 55,940 • DMHP • Dronabinol • HU-210 • JWH-133 • Levonantradol • Methanandamide • Nabilone • Nabitan • Parahexyl • Pravadoline • Rimonabant • THC-O-acetate • THC-O-phosphate • WIN 55,212-2
Endogenous cannabinoidsArachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "WIN_55,212-2". A list of authors is available in Wikipedia.
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