CAS No.63547-13-7,Adrafinil Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	63547-13-7
Name:	Adrafinil
Article Data:	2

Formula:	C₁₅H₁₅NO₃S
Molecular Weight:	289.355
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;
EINECS:	264-303-1
Density:	1.342 g/cm³
Melting Point:	150-160 °C
Appearance:	White, hygroscopic powder.
Hazard Symbols:	Xn
Risk Codes:	22
PSA:	85.61000
LogP:	3.28670

Synthetic route

: 63547-44-4
2-benzhydrylsulfanyl-N-hydroxyacetamide

: 63547-13-7
adrafinil

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 63547-13-7
adrafinil

: C50H45CuN5O4(1+)

: C49H45CuN5O3S(1+)

Conditions

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

Raw Materials

91-01-0

63547-22-8

63547-44-4

63547-23-9

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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.

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,