WIN 55,212-2

Drugbox
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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width= 160
CAS_number= 131543-23-2
ATC_prefix=
ATC_suffix=
PubChem= 5311501
DrugBank=
C=27 | H=26 | N=2 | O=3
molecular_weight = 522.61 g/mol
bioavailability=
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pregnancy_category =
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routes_of_administration=
smiles=CC1=C(C2=C3N1 [C@@H] (COC3=CC=C2)CN4CCOCC4)C(=O)C5=CC=CC6=CC=CC=C65

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. [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.] [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.] [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.]

WIN 55,212-2 is a potent cannabinoid receptor agonist [C.C. Felder "et al. Mol. Pharmacol." 1995 48 443] which has been found to be a potent analgesic [I.D. Meng "et al. Nature" 1998 395 381] in a rat model of neuropathic pain [U. Herzberg "et al. Neurosci. Lett." 1997 221 157] . It activates p42 and p44 MAP kinase via receptor-mediated signaling [M. Bouaboula "et al. Biochem. J." 1995 312 637] .

WIN55,212-2, alongside 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 full agonist at the CB1 receptor and has higher affinity than THC for the CB₁ receptor. [ 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. ] . 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 Fact|date=August 2007.

External links

* [http://www.biomol.com/SiteData/docs/productdata/CR105.pdf 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"
* [http://www.jneurosci.org/cgi/content/full/25/8/1904?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=1&andorexacttitle=and&andorexacttitleabs=and&fulltext=cannabinoid+alzheimer%27s&andorexactfulltext=and&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT JNeurosci.org] Prevention of Alzheimer's Disease Pathology by Cannabinoids: Neuroprotection Mediated by Blockade of Microglial Activation
* [http://www.newscientist.com/article.ns?id=dn10330 New Scientist] : Hope for cannabis-based drug for Alzheimer's

References