U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H26N2O3
Molecular Weight 426.5069
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WIN-55212-2

SMILES

CC1=C(C(=O)C2=C3C=CC=CC3=CC=C2)C4=C5N1[C@H](CN6CCOCC6)COC5=CC=C4

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 426.5069
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/9121688 | https://www.ncbi.nlm.nih.gov/pubmed/15728830 | https://www.ncbi.nlm.nih.gov/pubmed/11168547

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.

Originator

Curator's Comment: Sanofi Winthrop http://adisinsight.springer.com/drugs/800004262

Approval Year

TargetsConditions
Doses

Doses

DosePopulationAdverse events​
50 ug single, topical
Highest studied dose
Dose: 50 ug
Route: topical
Route: single
Dose: 50 ug
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol.
1992 Dec
Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor.
1992 Jan
Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids.
1993 Mar
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
The rodent amygdala contributes to the production of cannabinoid-induced antinociception.
2003
Cannabinoid receptor type 1 modulates excitatory and inhibitory neurotransmission in mouse colon.
2004 Jan
Retroinhibition of presynaptic Ca2+ currents by endocannabinoids released via postsynaptic mGluR activation at a calyx synapse.
2004 Jun 30
Periaqueductal grey CB1 cannabinoid and metabotropic glutamate subtype 5 receptors modulate changes in rostral ventromedial medulla neuronal activities induced by subcutaneous formalin in the rat.
2005
R-(+)-[2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)-pyrrolo-[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphtalenylmethanone (WIN-2) ameliorates experimental autoimmune encephalomyelitis and induces encephalitogenic T cell apoptosis: partial involvement of the CB(2) receptor.
2006 Dec 15
Evaluation of the role of nicotinic acetylcholine receptor subtypes and cannabinoid system in the discriminative stimulus effects of nicotine in rats.
2006 Jul 1
Neuropathic pain and the endocannabinoid system in the dorsal raphe: pharmacological treatment and interactions with the serotonergic system.
2006 Oct
Anti-inflammatory property of the cannabinoid agonist WIN-55212-2 in a rodent model of chronic brain inflammation.
2007 Feb 23
Long-term reduction of brain-derived neurotrophic factor levels and signaling impairment following prenatal treatment with the cannabinoid receptor 1 receptor agonist (R)-(+)-[2,3-dihydro-5-methyl-3-(4-morpholinyl-methyl) pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1- naphthalenylmethanone.
2007 Jun
Cannabinoids excite hypothalamic melanin-concentrating hormone but inhibit hypocretin/orexin neurons: implications for cannabinoid actions on food intake and cognitive arousal.
2007 May 2
CB1 receptor activation in the basolateral amygdala produces antinociception in animal models of acute and tonic nociception.
2007 May-Jun
Role of cannabinoid CB1 receptors and Gi/o protein activation in the modulation of synaptosomal Na+,K+-ATPase activity by WIN55,212-2 and delta(9)-THC.
2007 Oct 15
Mapping the structural requirements in the CB1 cannabinoid receptor transmembrane helix II for signal transduction.
2008 Apr
Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats.
2009 Jan
Patents

Sample Use Guides

Rat: 2.14, 4.3 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Radioligand binding studies were performed using male Sprague-Dawley rat cerebellar membranes from a 48,000 x g pellet which was washed twice by suspension in 20 mM HEPES buffer, pH 7. The final assay volume was 1 ml and included: 20 mM HEPES, pH 7; 0.5 nM [3H]-(R)-(+)-WIN 55212-2 (specific activity 59 Ci/mmOl, Dupont NEN); 1 mg/ml BSA; 100-120 ug cerebellar membrane protein and varying concentrations of competing compounds. WIN 55212-2 appeared to bind to a single class of sites (Kd = 2 nM: Bmax = 1.2 pmoles/mg protein) and was saturable, heat-labile, reversible and stereospecific.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:57:48 GMT 2025
Edited
by admin
on Mon Mar 31 21:57:48 GMT 2025
Record UNII
5H31GI9502
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(R)-(+)-WIN-55212-2
Preferred Name English
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
J442.901J
Code English
WIN 55212-2
Code 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
Code English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-WIN-55212-2
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
Code System Code Type Description
DRUG BANK
DB13950
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
PRIMARY
FDA UNII
5H31GI9502
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
PRIMARY
CAS
131543-22-1
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID40894849
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
PRIMARY
PUBCHEM
5311501
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
PRIMARY
CAS
131513-18-3
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
WIN 55,212-2
Created by admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING
IC50
TARGET -> AGONIST
Mouse AtT-20 neuroblastoma cells stably transfected with human CB2
EC50
TARGET -> AGONIST
BINDING
IC50
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Mouse AtT-20 neuroblastoma cells stably transfected with human CB1
EC50
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY