Adrafinil

Bezeichnung:Adrafinil

CAS-Nr63547-13-7

Englisch Name:Adrafinil

CBNumberCB7245226

SummenformelC15H15NO3S

Molgewicht289.35

MOL-Datei63547-13-7.mol

Adrafinil physikalisch-chemischer Eigenschaften

Schmelzpunkt	159-1600C
Dichte	1.342±0.06 g/cm3(Predicted)
storage temp.	-20°C Freezer
Löslichkeit	DMSO: 35 mg/mL
pka	8.22±0.20(Predicted)
Aggregatzustand	solid
Farbe	white
CAS Datenbank	63547-13-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
WGK Germany	3
RTECS-Nr.	AB8139500
Toxizität	LD50 in mice (mg/kg): <2048 i.p.; 1950 gastric admin (Lafon)

Gefahreninformationscode (GHS)

Adrafinil Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
Beschreibung
Adrafinil is a centrally-acting, αl-adrenergic agonist useful in the management of vigillance disturbances and depression in the elderly.
Chemische Eigenschaften
Light Pink Solid
Originator
Labs. L. Lafon (France)
Verwenden
a-Adrenergic agonist. Treatment of depression
Verwenden
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).
Trademarks
OLMIFON
Therapeutic Function
Psychostimulant

Adrafinil Upstream-Materialien And Downstream Produkte

63547-13-7, Adrafinil Verwandte Suche:

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