Adrafinil Chemical Properties

Melting point:

159-1600C

Density 

1.342±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

DMSO: 35 mg/mL

pka

8.22±0.20(Predicted)

form 

solid

color 

white

CAS DataBase Reference

63547-13-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

RTECS 

AB8139500

Toxicity

LD50 in mice (mg/kg): <2048 i.p.; 1950 gastric admin (Lafon)

MSDS

• Language:English Provider:2-[(Diphenylmethyl)sulfinyl]acetohydroxamic acid
• Language:English Provider:SigmaAldrich

Adrafinil Usage And Synthesis

Description

Adrafinil is a centrally-acting, αl-adrenergic agonist useful in the management of vigillance disturbances and depression in the elderly.

Chemical Properties

Light Pink Solid

Originator

Labs. L. Lafon (France)

Uses

a-Adrenergic agonist. Treatment of depression

Uses

α-Adrenergic agonist. Treatment of depression.

Definition

ChEBI: Adrafinil is a diarylmethane.

Manufacturing Process

7.6 g (0.1 mol) of thiourea and 100 ml of dematerialized water are introduced into a 500 ml three-neck flask equipped with a magnetic stirrer, a dropping funnel and a condenser; the mixture is heated to 50°C and 20.25 g (18 ml; 0.1 mol) of chlorodiphenylmethane are then added all at once. The solution is left refluxing until it has become limpid, and is then cooled to 20°C, and 200 ml of 2.5 N NaOH are added dropwise. So the sodium benzhydrylthiolate is obtained.
A solution of sodium 3-chloroacetate is added to the solution of sodium benzhydrylthiolate at about 60°C. Thereafter the temperature is raised to the boil, the mixture is left under reflux for about 0.5 h and is then cooled, filtered over charcoal and acidified with concentrated HCl, and 3- (benzhydrylthio)acetic acid are thus precipitated.
To the solution of 3-(benzhydrylthio)acetic acid in 1,2-dichloroethane, methanol and concentrated H2SO4 have been added. The whole is heated to the reflux temperature for about 5 h, cooled, and decanted, the aqueous phase is discarded and the organic phase is washed with a saturated sodium bicarbonate solution and then with water until the wash waters have a neutral pH. After drying over MgSO4 and evaporating the solvent, the 3- (benzhydrylthio)acetic acid methyl ester is obtained.
The 3-(benzhydrylthio)acetic acid methyl ester dissolved in methanol, is added to a solution of hydroxylamine base [prepared by neutralising 0.15 mol (10.4 g) of hydroxylamine hydrochloride with 0.15 mol of sodium methylate]. The whole is left at ordinary temperature (15°-25°C) for 48 h, the sodium chloride is filtered off, the methanol is evaporated, the residue is taken up with aqueous alkali, the solution is filtered over charcoal, the filtrate is acidified with concentrated HCl, and the 3-(benzhydrylthio)acethylhydroxamic acid (recrystallised from benzene) is thus obtained.
The 3-(benzhydrylthio)acethylhydroxamic acid, dissolved in anhydrous CH3COOH, is reacted with H2O2. The mixture is left at 40°-45°C for about 1.5 h, the acetic acid is evaporated and the residue is taken up in 50 ml of ethyl acetate; the 2-[(diphenylmethyl)sulfinyl]-N-hydroxyacetamide (CRL 40028) crystallises (recrystallised from isopropanol).

brand name

OLMIFON

Therapeutic Function

Psychostimulant

Adrafinil(63547-13-7)Related Product Information

• Dimethyl sulfoxide
• Ethyl 2-(Chlorosulfonyl)acetate
• Phenoxyacetyl chloride
• Acetone oxime
• Citric acid
• Ethyl acetohydroxamate
• Folic acid
• Sorafenib
• Dimethyl sulfone
• 2,3-Butanedione monoxime
• Acetohydroxamic acid
• Trimethylsulfoxonium iodide
• Pirfenidone
• 2-Butanone oxime
• Ascoric Acid
• Adrafinil
• SULFOXIDE
• 2-[(Diphenylmethyl)thio]acetamide