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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H26N2O3
Molecular Weight 426.508
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WIN-55212-2

SMILES

Cc1c(c2cccc3c2n1[C@]([H])(CN4CCOCC4)CO3)C(=O)c5cccc6ccccc65

InChI

InChIKey=HQVHOQAKMCMIIM-HXUWFJFHSA-N
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

HIDE SMILES / InChI

Molecular Formula C27H26N2O3
Molecular Weight 426.508
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

WIN 55212-2 is the synthetic cannabimimetic compound. It is a potent aminoalkylindole cannabinoid receptor agonist. WIN 55,212-2 increases expression of anti-oxidant Cu/Zn SOD and is able to prevent inflammation induced by Aβ1-42 in cultured astrocytes. It exerts neuroprotective and anti-inflammatory actions against Aβ damage through both CB₁ and CB₂ receptors. WIN 55212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain. In the clinical trial, it was revealed that WIN 55212-2, applied topically, decreases the intraocular pressure of human glaucoma resistant to conventional therapies within the first 30 min.

Approval Year

Doses

Doses

DosePopulationAdverse events​
50 ug single, topical (total daily dose)
Highest studied dose
Dose: 50 ug
Route: topical
Route: single
Dose: 50 ug
Sources:
unhealthy, ADULT
n = 8
Health Status: unhealthy
Condition: glaucoma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 8
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.
1995 Sep
Molecular cloning, expression and function of the murine CB2 peripheral cannabinoid receptor.
1996 Jun 7
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.
1996 Sep
N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A) interaction with LYS 3.28(192) is crucial for its inverse agonism at the cannabinoid CB1 receptor.
2002 Dec
The heritability of antinociception: common pharmacogenetic mediation of five neurochemically distinct analgesics.
2003 Feb
Long-term effects on cortical glutamate release induced by prenatal exposure to the cannabinoid receptor agonist (R)-(+)-[2,3-dihydro-5-methyl-3-(4-morpholinyl-methyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone: an in vivo microdialysis study in the awake rat.
2004
Cannabinoid receptor type 1 modulates excitatory and inhibitory neurotransmission in mouse colon.
2004 Jan
Neurochemical evidence that stimulation of CB1 cannabinoid receptors on GABAergic nerve terminals activates the dopaminergic reward system by increasing dopamine release in the rat nucleus accumbens.
2009 Jun
Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine.
2009 Mar 10
Cannabinoid CB1 and cholecystokinin CCK2 receptors modulate, in an opposing way, electrically evoked [3H]GABA efflux from rat cerebral cortex cell cultures: possible relevance for cortical GABA transmission and anxiety.
2009 May
Endocannabinoids suppress excitatory synaptic transmission to dorsal raphe serotonin neurons through the activation of presynaptic CB1 receptors.
2009 Oct
Patents

Sample Use Guides

25 or 50 ug
Route of Administration: Topical
ChIP assays were performed to evaluate whether R(+)WIN 55,212-2 could affect the binding of the NF-kB subunit, p65, to the ICAM-1 and IL-8 promoters. 1321N1 astrocytoma were pre-treated with or without R(+)WIN 55,212-2 (20 uM) for 1 h prior to stimulation for a further 1 h in the absence or presence of IL-1 (10 ng/ml). p65 was absent at the promoters in unstimulated 1321N1 cells, but after 1-h stimulation with IL-1, p65 was detected at both promoters.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:41:49 UTC 2021
Edited
by admin
on Sat Jun 26 11:41:49 UTC 2021
Record UNII
5H31GI9502
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
WIN-55212-2
Code English
METHANONE, (2,3-DIHYDRO-5-METHYL-3-(4-MORPHOLINYLMETHYL)PYRROLO(1,2,3-DE)-1,4-BENZOXAZIN-6-YL)-1-NAPHTHALENYL-, (+)-
Systematic Name English
(R)-(+)-WIN-55212-2
Common Name English
J442.901J
Code English
WIN 55212-2
Common Name English
METHANONE, ((3R)-2,3-DIHYDRO-5-METHYL-3-(4-MORPHOLINYLMETHYL)PYRROLO(1,2,3-DE)-1,4-BENZOXAZIN-6-YL)-1-NAPHTHALENYL-
Systematic Name English
(R)-WIN-55212
Common Name English
Code System Code Type Description
DRUG BANK
DB13950
Created by admin on Sat Jun 26 11:41:49 UTC 2021 , Edited by admin on Sat Jun 26 11:41:49 UTC 2021
PRIMARY
FDA UNII
5H31GI9502
Created by admin on Sat Jun 26 11:41:49 UTC 2021 , Edited by admin on Sat Jun 26 11:41:49 UTC 2021
PRIMARY
CAS
131543-22-1
Created by admin on Sat Jun 26 11:41:49 UTC 2021 , Edited by admin on Sat Jun 26 11:41:49 UTC 2021
PRIMARY
PUBCHEM
5311501
Created by admin on Sat Jun 26 11:41:49 UTC 2021 , Edited by admin on Sat Jun 26 11:41:49 UTC 2021
PRIMARY
CAS
131513-18-3
Created by admin on Sat Jun 26 11:41:49 UTC 2021 , Edited by admin on Sat Jun 26 11:41:49 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
WIN 55,212-2
Created by admin on Sat Jun 26 11:41:49 UTC 2021 , Edited by admin on Sat Jun 26 11:41:49 UTC 2021
PRIMARY
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