View source for WIN 55,212-2

{{Drugbox|
|IUPAC_name = (R)-(+)-[2,3-Dihydro-5-methyl-<br>3-(4-morpholinylmethyl)pyrrolo<br>[1,2,3-de)-1,4-benzoxazin-6-yl]-<br>1-napthalenylmethanone
| image = WIN 55,212-2-2D-skeletal.svg
| width = 200px
| CAS_number= 131543-23-2   
| ATC_prefix=
| ATC_suffix=
| PubChem= 5311501
| IUPHAR_ligand = 733
| DrugBank=
| C=27 | H=26 | N=2 | O=3
| molecular_weight = 522.61 g/mol
| bioavailability=
| metabolism = 
| elimination_half-life= 
| excretion = 
| pregnancy_category =
| legal_status = 
| 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 chemical described as an aminoalkylindole derivative, that produces effects similar to those of [[Cannabinoid]] derivatives such as [[Tetrahydrocannabinol|THC]] but has an entirely different [[chemical structure]].<ref>Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR. Aminoalkylindole Analogs: Cannabimimetic Activity of a Class of Compounds Structurally Distinct from Δ<sup>9</sup>-Tetrahydrocannabinol. ''Journal of Pharmacology and Experimental Therapeutics''. 1992; 263(3):1118-1126.</ref><ref>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.</ref><ref>{{Cite pmid|12228183}}</ref>

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

WIN 55,212-2, 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 anti-inflamatory action is induced through the agonization of [[cannabinoid receptor]]s which prevents [[microglia]]l activation that elicits the inflammation. Additionally, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.

WIN 55212-2 is a full agonist at the CB1 receptor and has higher affinity than [[tetrahydrocannabinol|THC]] for the CB<sub>1</sub> receptor.<ref>{{Cite pmid|8450470}}</ref>. WIN 55212-2 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}}

[[File:Pancreatic stellate cell cropped.png|thumb|left|[[Pancreatic stellate cell]]s. The cells in the lower frame are under the action of WIN 55,212-2. They are thought to assume a more "quiescent" phenotype. From Michalski et al., 2008.<ref name="PSCWIN">{{Cite pmid|18301776}}</ref>]]
==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 ==
{{reflist}}

{{Cannabinoids}}

[[Category:Cannabinoids]]
[[Category:Aminoalkylindoles]]
[[Category:Naphthoylindoles]]
[[Category:Morpholines]]
[[Category:Pyrrolobenzoxazines]]
{{cannabinoid-stub}}
[[Category:2Fix]]