1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE Property

Melting point:

186-186.5 °C

Boiling point:

655.9±50.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Desiccate at RT

solubility 

DMSO: >10mg/mL

pka

6.01±0.10(Predicted)

form 

A crystalline solid

color 

white to off-white

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE Chemical Properties,Usage,Production

Description

Linopirdine 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; K_v7.2/7.3; 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).

Uses

Alzheimer’s disease treatment (cognition enhancer).

Definition

ChEBI: Linopirdine is a member of indoles.

Biological Activity

Blocker of KCNQ voltage-gated potassium channels; blocks KCNQ2+3/M-currents (IC 50 = 4-7 μ M) and KCNQ1 homomeric channels (IC 50 = 8.9 μ M). Augments hippocampal ACh release and is a cognitive enhancer following oral administration in vivo .