WIN 55,212-2

WIN 55,212-2
Legal status

Legal status	CA: Schedule II UK: Class B
Identifiers
IUPAC name (11R)-2-methyl-11-[(morpholin-4-yl)methyl]-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4(12),5,7-tetraene
CAS Number	131543-22-1^N
PubChem (CID)	5311501
IUPHAR/BPS	733
ChemSpider	4470978^N
UNII	5H31GI9502^N
ChEBI	CHEBI:73295^N
ChEMBL	CHEMBL188^N
Chemical and physical data
Formula	C₂₇H₂₆N₂O₃
Molar mass	426.52 g/mol
3D model (Jmol)	Interactive image
SMILES CC1=C(C2=C3N1[C@@H](COC3=CC=C2)CN4CCOCC4)C(=O)C5=CC=CC6=CC=CC=C65
InChI InChI=1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1^N Key:HQVHOQAKMCMIIM-HXUWFJFHSA-N^N
^NY (what is this?)

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.

WIN 55,212-2 is a potent cannabinoid receptor agonist that has been found to be a potent analgesic in a rat model of neuropathic pain. It activates p42 and p44 MAP kinase via receptor-mediated signaling.

At 5 µM WIN 55,212-2 inhibit ATP production in sperm in a CB₁ receptor-dependent fashion.

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.

WIN 55,212-2 is a full agonist at the CB₁ cannabinoid receptor (K_i = 1.9 nM) and has much higher affinity than THC (K_i = 41 nM) for this receptor.

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Wikipedia