(3E)-3-((2,4-Dimethoxyphenyl)methylene)-3,4,5,6-tetrahydro-2,3'-bipyridine
Basic information
- CAS
148372-04-7- Standard SMILES
COc1ccc(/C=C2\CCCN=C2c2cccnc2)c(OC)c1- InChIKey
RPYWXZCFYPVCNQ-RVDMUPIBSA-N- Molecular formula
- C19H20N2O2
- Average molar mass
- 308.4 g/mol
- Monoisotopic mass
- 308.15247789
Overview
DMXB-A is a dimethoxybenzene.
Names & identifiers
- Preferred name
- (3E)-3-((2,4-Dimethoxyphenyl)methylene)-3,4,5,6-tetrahydro-2,3'-bipyridine
- IUPAC
- 3-[(5E)-5-[(2,4-dimethoxyphenyl)methylidene]-3,4-dihydro-2H-pyridin-6-yl]pyridine
- English name
- GTS-21
- Molecular formula
- C19H20N2O2
- Molecular weight
- 308.37
Names & synonyms
Gts-21148372-04-7Dimethoxybenzylidene anabaseine3-[(5E)-5-[(2,4-dimethoxyphenyl)methylidene]-3,4-dihydro-2H-pyridin-6-yl]pyridine8S399XDN2KDMBX-ADTXSID701027513(3E)-3-((2,4-Dimethoxyphenyl)methylene)-3,4,5,6-tetrahydro-2,3'-bipyridine3-((5E)-5-((2,4-dimethoxyphenyl)methylidene)-3,4-dihydro-2H-pyridin-6-yl)pyridineRefChem:1050205DTXCID9015116893-((3E)-3-((2,4-dimethoxyphenyl)methylidene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine
Show more names
3-(2,4-Dimethoxy-Benzylidene)-3,4,5,6-Tetrahydro-[2,3']Bipyridinyl3-[(2,4-dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-2,3'-Bipyridine2,3'-Bipyridine, 3-[(2,4-dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-, (3E)-
CHEMBL1347132,4-Dimethoxybenzylidene anabaseine3-(2,4-Dimethoxybenzylidene)-3,4,5,6-tetrahydro-2,3'-bipyridine(e)-3-(2,4-dimethoxybenzylidene)-3,4,5,6-tetrahydro-2,3'-bipyridine(3e)-3-[(2,4-Dimethoxyphenyl)methylidene]-3,4,5,6-Tetrahydro-2,3'-Bipyridine2,3'-Bipyridine, 3-[(2,4-dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-, hydrochloride (1:2), (3E)-GTS 21 dihydrochlorideGts 21
Database identifiers
- CAS
148372-04-7- PubChem CID
- 5310985
- DTXSID
DTXSID701027513- ChEMBL
CHEMBL134713- ChEBI
CHEBI:188219- UNII
- 8S399XDN2K
- Nikkaji
- J634.185C、J674.426E
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 43.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 447
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.82
Physicochemical properties
- FDA UNII
- 8 S399XDN2K · 8S399XDN2K
Chemistry & industry
Pharmacology
Mechanism of Action
Auditory sensory gating, a biological measurement of the ability to suppress the evoked response to the second of two auditory stimuli, is diminished in people with schizophrenia. Deficits in sensory gating are associated with attentional impairment, and may contribute to cognitive symptoms and perceptual disturbances. This inhibitory process, which involves the alpha(7) nicotinic receptor mediated release of gamma-aminobutyric acid (GABA) by hippocampal interneurons, represents a potential new target for therapeutic intervention in schizophrenia. GTS-21 is an orally active alpha-7 nicotinic acetylcholine (nACh) receptor agonist.
Metabolism/Metabolites
GTS-21 was O-demethylated to yield compounds that were then subject to glucuronidation. Three of the metabolites in rat urine were isolated and characterized as 4-OH-GTS-21, 4-OH-GTS-21 glucuronide and 2-OH-GTS-21 glucuronide. The major urinary metabolites were 4-OH-GTS-21 glucuronide and 2-OH-GTS-21 glucuronide. In vitro chemical inhibition of cytochrome P450 in human liver microsomes indicated that CYPIA2 and CYP2E1 were the isoforms primarily responsible for the O-demethylation of GTS-21, with some contribution from CYP3A.
Gts-21 has known human metabolites that include 2-hydroxy-GTS-21 and 4-hydroxy-GTS-21.
Absorption, Distribution and Excretion
Rapidly and extensively absorbed after oral administration. In rat, GTS-21 showed linear pharmacokinetics over doses ranging from 1 to 10 mg/kg with an absolute bioavailability of 23%. In dog, the absolute bioavailability was 27% at an oral dose of 3 mg/kg.
Applications
Uses2,4-Dimethoxybenzylidene Anabaseine selectively activates rat alpha7 receptors and improves memory-related behaviors in a mecamylamine-sensitive manner.
Additional notes
DefinitionChEBI: DMXB-A is a dimethoxybenzene.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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