Basic information
- CAS
105431-72-9- Standard SMILES
O=C1N(c2ccccc2)c2ccccc2C1(Cc1ccncc1)Cc1ccncc1- InChIKey
YEJCDKJIEMIWRQ-UHFFFAOYSA-N- Molecular formula
- C26H21N3O
- Average molar mass
- 391.5 g/mol
- Monoisotopic mass
- 391.1684623
Overview
Linopirdine is a member of indoles.
Names & identifiers
- Preferred name
- Linopirdine
- IUPAC
- 1-phenyl-3,3-bis(pyridin-4-ylmethyl)indol-2-one
- English name
- 1,3-Dihydro-1-phenyl-3,3-bis(4-pyridinylmethyl)-2H-indol-2-one dihydrochloride
- Molecular formula
- C26H21N3O
- Molecular weight
- 391.46
Names & synonyms
Linopirdine105431-72-9Dup 9961-phenyl-3,3-bis(pyridin-4-ylmethyl)indol-2-oneDuP-996LinopirdinaI5TB3NZ94T2H-Indol-2-one, 1,3-dihydro-1-phenyl-3,3-bis(4-pyridinylmethyl)-1-phenyl-3,3-bis(4-pyridylmethyl)indolin-2-one3,3-bis(4-pyridylmethyl)-1-phenylindolin-2-onelinopirdinum3,3-dipyridylmethyl-1-phenyl-2-indolinone
Show more names
linopiridineLinopirdine2HClLINOPIRDINE (DUP996)Linopirdine, 10 mM in DMSOLINOPIRDINE DIHYDROCHLORIDE1-Phenyl-3,3-bis(4-pyridinylmethyl)-2,3-dihydro-1H-indole-2-one1-Phenyl-3,3-bis(pyridin-4-ylmethyl)indolin-2-one dihydrochloride
RefChem:924805N06BX091,3-Dihydro-1-phenyl-3,3-bis(4-pyridinylmethyl)-2H-indol-2-one1-Phenyl-3,3-bis(pyridin-4-ylmethyl)indolin-2-oneDTXSID6045163MFCD008672161-Phenyl-3,3-bis(4-pyridinylmethyl)-2-indolinoneNCGC00015590-03
Database identifiers
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 46.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 555
Physicochemical properties
- Melting point
- 186 · 186-186.5 °C
- Boiling point
- 655.9 · 655.9±50.0 °C(Predicted)
- Density
- 1 · 1+-.0.06 g/cm3(Predicted)
- storage temp.
- Desiccate at RT
- solubility
- 10 mg/mL · DMSO: >10mg/mL
- pka
- 6.01 · 6.01±0.10(Predicted)
- form
- A crystalline solid
- color
- white to off-white
- FDA UNII
- 5 TB3NZ94T · I5TB3NZ94T
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological Classification
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
A class of drugs that act by inhibition of potassium efflux through cell membranes. Blockade of potassium channels prolongs the duration of ACTION POTENTIALS. They are used as ANTI-ARRHYTHMIA AGENTS and VASODILATOR AGENTS.
Applications
DescriptionLinopirdine is an enhancer of the stimulus-evoked but not basal release of several neurotransmitters, including acetylcholine, dopamine, serotonin, and glutamate. It increases acetylcholine release in rat hippocampal CA1 neurons by blocking voltage-gated, calcium-activated and leak (M-type; Kv7.2/7.3; KCNQ2/3) K+ current with an IC50 value of 2.4 μM. Inhibition of M-channels is reported to result in the depolarization of CA3 pyramidal neurons and activated presynaptic voltage-gated P/Q- and N-type calcium channels, which leads to Ca2+ influx and increased neurotransmitter release. Linopirdine has been shown to produce a number of effects including EEG patterns of enhanced vigilance, induction of c-fos expression in cerebral cortex, reduction of the increase of cerebral glucose utilization induced by hypoxia, and improved performance in animal models of learning and memory. Linopirdine has also been identified as an agonist of transient receptor potential vanilloid type 1 (EC50 = 115 μM in HEK293 cells voltage clamped at -60 mV).
UsesAlzheimer’s disease treatment (cognition enhancer).
Suppliers39 total
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
Related reactions
8 records
Compound notes
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