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2-benzhydrylsulfanyl-N-hydroxyacetamide
adrafinil
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid at 40℃; | 72% |
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 |
(benzhydrylthio)acetic acid
adrafinil
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 |
(diphenylmethyl)(ethyl acetate)sulfide
adrafinil
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 |
adrafinil
Conditions | Yield |
---|---|
In water; acetonitrile pH=6.0; Inert atmosphere; |
Conditions | Yield |
---|---|
In water; acetonitrile pH=6.0; Inert atmosphere; |
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.
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%.
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, |