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Adrafinil

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Name

Adrafinil

EINECS 264-303-1
CAS No. 63547-13-7 Density 1.342 g/cm3
PSA 85.61000 LogP 3.28670
Solubility N/A Melting Point 150-160 °C
Formula C15H15NO3S Boiling Point N/A
Molecular Weight 289.355 Flash Point N/A
Transport Information N/A Appearance White, hygroscopic powder.
Safety Risk Codes 22
Molecular Structure Molecular Structure of 63547-13-7 (Adrafinil) Hazard Symbols HarmfulXn
Synonyms

Adrafinil;CRL 40028;Olmifon;2-[(Diphenylmethyl)sulfinyl]-N-hydroxyacetamide;Acetamide, 2-[(diphenylmethyl)sulfinyl]-N-hydroxy-;2-((Diphenylmethyl)sulfinyl)acetohydroxamic acid;2-((Diphenylmethyl)sulfinyl)acetohydroxamsaeure;2-((Diphenylmethyl)sulfinyl)-N-hydroxyacetamide;2-(Benzhydrylsulfinyl)acetohydroxamic acid;2-(Diphenyl-methanesulfinyl)-N-hydroxy-acetamide;BRN 1990030;

Article Data 2

Adrafinil Synthetic route

63547-44-4

2-benzhydrylsulfanyl-N-hydroxyacetamide

63547-13-7

adrafinil

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid at 40℃;72%
91-01-0

1,1-Diphenylmethanol

BF3(C2H5)2O

BF3(C2H5)2O

63547-13-7

adrafinil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / trifluoroacetic acid / 3 h / 20 °C
2: 99 percent / H2SO4 / Heating
3: 92 percent / hydroxylamine hydrochloride; KOH / methanol / 0.25 h
4: 72 percent / aq. H2O2; acetic acid / 40 °C
View Scheme
63547-22-8

(benzhydrylthio)acetic acid

63547-13-7

adrafinil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / H2SO4 / Heating
2: 92 percent / hydroxylamine hydrochloride; KOH / methanol / 0.25 h
3: 72 percent / aq. H2O2; acetic acid / 40 °C
View Scheme
63547-23-9

(diphenylmethyl)(ethyl acetate)sulfide

63547-13-7

adrafinil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / hydroxylamine hydrochloride; KOH / methanol / 0.25 h
2: 72 percent / aq. H2O2; acetic acid / 40 °C
View Scheme
63547-13-7

adrafinil

(meso-1,2-N,N’-bisquinoline-2-methyl-diphenyl-1,2-diamine) zinc(II) trifluoromethanesulfonate

C49H45N5O3SZn(1+)

Conditions
ConditionsYield
In water; acetonitrile pH=6.0; Inert atmosphere;
63547-13-7

adrafinil

C50H45CuN5O4(1+)

C49H45CuN5O3S(1+)

Conditions
ConditionsYield
In water; acetonitrile pH=6.0; Inert atmosphere;

Adrafinil History

Adrafinil (CAS NO.63547-13-7) was discovered in the late 1970s by scientists working with the French pharmaceutical company Group Lafon. First offered in France in 1986 as an experimental treatment for narcolepsy, Lafon later developed modafinil, the primary metabolite of adrafinil. Modafinil possesses greater selective alpha-1 adrenergic activity than adrafinil without the side effects of stomach pain, skin irritations, feelings of tension, and increases in liver enzyme levels.
It is important to monitor the liver of an individual using adrafinil. It can cause liver damage in some instances. 

Adrafinil Specification

The Adrafinil with CAS registry number of 63547-13-7 is also known as 2-[(Diphenylmethyl)sulfinyl]-N-hydroxyacetamide. The IUPAC name is 2-Benzhydrylsulfinyl-N-hydroxyacetamide. It belongs to product categories of Aromatics Compounds; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds. This chemical is a light pink solid and its EINECS registry number is 264-303-1. In addition, the formula is C15H15NO3S and the molecular weight is 289.35. This chemical is harmful if swallowed.

Physical properties about Adrafinil are: (1)ACD/LogP: 1.596; (2)ACD/LogD (pH 5.5): 1.60; (3)ACD/LogD (pH 7.4): 1.53; (4)ACD/BCF (pH 5.5): 9.60; (5)ACD/BCF (pH 7.4): 8.34; (6)ACD/KOC (pH 5.5): 175.52; (7)ACD/KOC (pH 7.4): 152.63; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.653; (12)Molar Refractivity: 78.858 cm3; (13)Molar Volume: 215.542 cm3; (14)Polarizability: 31.262 10-24cm3; (15)Surface Tension: 67.25 dyne/cm; (16)Density: 1.342 g/cm3

Preparation of Adrafinil: it is prepared by reaction of diphenyl methyl bromide with thiourea. This reaction needs reagent NaOH. After reacting with chloroacetic acid, hydrochloric acid amine and hydrogen peroxide, the product is obtained. The yield is about 73%.

Adrafinil is prepared by reaction of diphenyl methyl bromide with thiourea.

Uses of Adrafinil: it is used as non-amphetamine-type psychostimulant and can wake up and raise awareness. For the elderly arousal disorder and depressive symptoms in symptomatic treatment.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17);
(2)InChIKey=CGNMLOKEMNBUAI-UHFFFAOYSA-N;
(3)SmilesC(C[S@@](=O)C(c1ccccc1)c1ccccc1)(=O)NO

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 859mg/kg (859mg/kg) BEHAVIORAL: EXCITEMENT Journal de Pharmacologie. Vol. 17, Pg. 37, 1986.
mouse LD50 oral 1950mg/kg (1950mg/kg)   United States Patent Document. Vol. #4066686,