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Adrafinil

CAS No.
63547-13-7
Chemical Name:
Adrafinil
Synonyms
OLMIFON;CRL 40028;ADRAFINIL;Olmifon sky;Adrafinil API;A flexor sorafenib;ADRAFINIL (OLMIFON);Adrafinil/CRL-40028;Adrafinil USP/EP/BP;Nootropics Adrafinil
CBNumber:
CB7245226
Molecular Formula:
C15H15NO3S
Molecular Weight:
289.35
MDL Number:
MFCD00865357
MOL File:
63547-13-7.mol
Last updated:2023-06-08 09:01:58

Adrafinil 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)
FDA UNII BI81Z4542G
ATC code N06BX17

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
RTECS  AB8139500
Toxicity LD50 in mice (mg/kg): <2048 i.p.; 1950 gastric admin (Lafon)
NFPA 704
0
2 0

Adrafinil Chemical Properties,Uses,Production

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

α-Adrenergic agonist. Treatment of depression.

Uses

a-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

2-((diphenylmethyl)sulfinyl)-acetohydroxamicaci 2-((diphenylmethyl)sulfinyl)-n-hydroxy-acetamid 2-((diphenylmethyl)sulfinyl)-n-hydroxyacetamide 2-(benzhydrylsulfinyl)acetohydroxamicacid ADRAFINIL 2-[(DIPHENYLMETHYL)SULFINYL]ACETOHYDROXAMIC ACID CRL 40028 OLMIFON ADRAFINIL (OLMIFON) 2-[(Diphenylmethyl)sulfinyl]acetohydroxamic acid, CRL 40028, Olmifon 2-[(Diphenylmethyl)sulfinyl]-N-hy-dmxyacetamide Acetohydroxamic acid, 2-((diphenylmethyl)sulfinyl)- (Benzhydrylsulfinyl)acetohydroximic acid Adrafinil,2-[(Diphenylmethyl)sulfinyl]acetohydroxamic acid, CRL 40028, Olmifon Adrafinil API AcetaMide,2-[(diphenylMethyl)sulfinyl]-N-hydroxy- A flexor sorafenib Adrafinil/CRL-40028 Olmifon sky 63547-13-7 White Adrafinil Power ADRAFINIL / ADRAFINIL Adrafinil USP/EP/BP Smart Drug Nootropics Crl-40, 941 Nootropics Adrafinil 63547-13-7 3547-13-7 C15H15NO3S research chemical pharmacetical intermediate Adrafinil Aromatics Compounds Aromatics Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds