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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H26N2O3.CH4O3S
Molecular Weight 522.613
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WIN-55212-2 MESYLATE

SMILES

CS(O)(=O)=O.CC1=C(C(=O)C2=CC=CC3=C2C=CC=C3)C4=C5N1[C@H](CN6CCOCC6)COC5=CC=C4

InChI

InChIKey=FSGCSTPOPBJYSX-VEIFNGETSA-N
InChI=1S/C27H26N2O3.CH4O3S/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;1-5(2,3)4/h2-11,20H,12-17H2,1H3;1H3,(H,2,3,4)/t20-;/m1./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Assessment of the role of CB1 receptors in cannabinoid anticonvulsant effects.
2001 Sep 28
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
Desensitization of cannabinoid-mediated presynaptic inhibition of neurotransmission between rat hippocampal neurons in culture.
2002 Mar
Effects of Win 55,212-2 on hippocampal CA1 long-term potentiation in experiments controlled for basal glutamatergic synaptic transmission.
2002 Oct 25
The rodent amygdala contributes to the production of cannabinoid-induced antinociception.
2003
The heritability of antinociception: common pharmacogenetic mediation of five neurochemically distinct analgesics.
2003 Feb
Milk intake and survival in newborn cannabinoid CB1 receptor knockout mice: evidence for a "CB3" receptor.
2003 Feb 7
Functional tolerance and blockade of long-term depression at synapses in the nucleus accumbens after chronic cannabinoid exposure.
2003 Jun 15
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
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
Cannabinoid receptor type 1 located on presynaptic terminals of principal neurons in the forebrain controls glutamatergic synaptic transmission.
2006 May 24
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
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine.
2008 Oct 15
Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats.
2009 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 Dec 16 10:37:34 GMT 2023
Edited
by admin
on Sat Dec 16 10:37:34 GMT 2023
Record UNII
2J851TP7VJ
Record Status Validated (UNII)
Record Version
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Name Type Language
WIN-55212-2 MESYLATE
Common Name English
(R)-(+)-(2,3-DIHYDRO-5-METHYL-3-(4-MORPHOLINYLMETHYL)PYRROLO(1,2,3-DE)-1,4-BENZOXAZIN-6-YL)-1-NAPTHALENYLMETHANONE
Systematic Name English
WIN-55212-2 MESILATE
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-, METHANESULFONATE (1:1)
Systematic Name English
(R)-(+)-WIN 55212-2 MESYLATE
Common Name English
WIN 55212-2 MESYLATE
Common Name English
Code System Code Type Description
PUBCHEM
6604176
Created by admin on Sat Dec 16 10:37:34 GMT 2023 , Edited by admin on Sat Dec 16 10:37:34 GMT 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
WIN 55-212-2
Created by admin on Sat Dec 16 10:37:34 GMT 2023 , Edited by admin on Sat Dec 16 10:37:34 GMT 2023
PRIMARY
DRUG BANK
DBSALT002620
Created by admin on Sat Dec 16 10:37:34 GMT 2023 , Edited by admin on Sat Dec 16 10:37:34 GMT 2023
PRIMARY
FDA UNII
2J851TP7VJ
Created by admin on Sat Dec 16 10:37:34 GMT 2023 , Edited by admin on Sat Dec 16 10:37:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID50424974
Created by admin on Sat Dec 16 10:37:34 GMT 2023 , Edited by admin on Sat Dec 16 10:37:34 GMT 2023
PRIMARY
CAS
131543-23-2
Created by admin on Sat Dec 16 10:37:34 GMT 2023 , Edited by admin on Sat Dec 16 10:37:34 GMT 2023
PRIMARY
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ACTIVE MOIETY