CNS-1102 Chemical Properties

Melting point:

223-225°

storage temp. 

2-8°C

solubility 

H₂O: 17 mg/mL, soluble

form 

solid

color 

white

Water Solubility 

Water: 50 mM

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

CNS-1102 Usage And Synthesis

Originator

Aptiganel,Oregon State University

Uses

Stroke and traumatic brain injury treatment (NMDA ion channel blocker).

Uses

Cerestat is a Potent and Noncompetitive NMDA receptor antagonist, Significantly reduced ischemic volume in rat focal cerebral ischemia model. (2). It is a neuroprotective, decreases contusion volume, reduced hemispheric swelling and ICP and also increases CPP. (3)

Manufacturing Process

A solution of m-ethylphenylcyanamide (1.46 g, 10 mmol) and sodium hydride (480 mg, 20 mmol, prewashed with hexane) in anhydrous THF (10 ml) was heated at 80-85°C for 2.5 hours. After it was allowed to cool to room temperature, methyl iodide (3.5 g, 25 mmol) was added and stirring continued at room temperature for 2 hours. Methanol (10 ml) followed by water (20 ml) was added and the reaction mixture was extracted with dichloromethane (3x25 ml). Concentration of the organic layer followed by flash chromatography on SiO2 afforded N-(m-ethylphenyl)-N-methylcyanamide (960 mg, 60%) as a colorless liquid: IR (film): 2220, 3400cm-1.
A mixture of m-ethylphenyl-N-methylcyanamide (520 mg, 3.25 mmol) and 1- aminonaphthalene hydrochloride (508 mg, 3.25 mmol) was placed in a preheated oil bath at 160°C for 3 hours and then allowed to cool to room temperature. The resulting solid was taken into dichloromethane and washed with 10% sodium hydroxide solution. The organic layer was concentrated and the resulting residue was dissolved in absolute ethanol (2 ml) and treated with dilute hydrochloric acid. It was concentrated and the solid was twice recrystallized from absolute ethanol-ether to give N-(1-naphthyl)-N'-(methylphenyl)- N'-methylguanidine hydrochloride (403 mg, 37%) as off-white needles, melting point 223-225°C.

brand name

Cerestat (Cambridge).

Therapeutic Function

NMDA antagonist

Biochem/physiol Actions

CNS-1102 acts as a neuroprotective agent and might exhibit therapeutic effects against acute stroke and traumatic brain injury.

storage

Store at +4°C