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Modafinil

Modafinil Basic information
Description References
Product Name:Modafinil
Synonyms:MODAFINIL;Acetamide, 2-[(diphenylmethyl)sulfinyl]-;Modiodal;(Benzhydrylsulfinyl)acetamide;Modafinilrac;2-[di(phenyl)methylsulfinyl]ethanamide;Modafinil,2-[(Diphenylmethyl)sulfinyl]-acetamide;Modafinil CIV (200 mg)F0D3510.997mg/mg(ai)
CAS:68693-11-8
MF:C15H15NO2S
MW:273.35
EINECS:640-968-7
Product Categories:LOTENSIN;Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
Mol File:68693-11-8.mol
Modafinil Structure
Modafinil Chemical Properties
Melting point 164-166°C
Boiling point 559.1±50.0 °C(Predicted)
density 1.283±0.06 g/cm3(Predicted)
Fp 2℃
storage temp. Store at +4°C
solubility DMSO: 18 mg/mL, soluble
pka14.88±0.40(Predicted)
form white solid
color white
CAS DataBase Reference68693-11-8(CAS DataBase Reference)
Safety Information
Hazard Codes T+,Xn,F
Risk Statements 26/27/28-36-20/21/22-11
Safety Statements 24/25-45-36/37/39-22-36/37-16
RIDADR UN 1648 3 / PGII
WGK Germany 3
HS Code 29309090
Hazardous Substances Data68693-11-8(Hazardous Substances Data)
MSDS Information
ProviderLanguage
2-[(Diphenylmethyl)sulfinyl]-acetamide English
SigmaAldrich English
Modafinil Usage And Synthesis
DescriptionMarketed as a wakefulness promoting agent, modafinil belongs to the group of medicines known as central nervous system (CNS) stimulants, which is commonly used to promote wakefulness and reduce excessive daytime sleepiness in patients with narcolepsy, obstructive sleep apnea, hypopnea syndrome, shift-work sleep disorder or circadian rhythm sleep disorder. Besides, recently studies have showed that modafinil may be effective to help cocaine addicts fight against their addiction.
The sleepiness-preventing effects of modafinil functions by stimulating certain parts of the brain, in which the neurons are activated by modafinil. It binds to the dopamine reuptake pump so as to inhibit the reuptake of dopamine from the cell, while the extracellular dopamine increases, thus preventing drowsiness and keeping people from falling asleep.
Referenceshttps://en.wikipedia.org/wiki/Modafinil
http://bodyandhealth.canada.com/drug/getdrug/apo-modafinil
https://www.drugbank.ca/drugs/DB00745
DescriptionModafinil, a centrally active α1-adrenergic agonist, was marketed in France as a psychostimulant for the treatment of narcolepsy and idiopathic hypersomnia including Gelineau's syndrome. In monkeys, modafinil was found to induce potent behavioral stimulation and awakening without stereotyped behavior. In narcoleptic patients, modafinil reduces the daily number of sleep attacks significantly and markedly improves performance. The mechanism of action for its locomotor effects was reported to be due to the stimulation of the central α1-adrenergic system, opposite to amphetamine and methylphenidate, which act mainly by dopaminergic mechanisms. Modafinil has been reported to exhibit minimal peripheral side effects at therapeutic doses and appears to have low abuse potential. The use of modafinil in the treatment of cerebral infarction and ischemia has been claimed.
Chemical PropertiesCrystalline Solid
OriginatorLafon (France)
UsesACE inhibitor, antihypertensive
UsesModafinil is an α-1-adrenergic agonist. Modafinil is a CNS stimulant; psychostimulant that displays neuroprotective and antiparkinsonian activity in a primate model of Parkinson's disease.
UsesA central nervous system vigilance promoting agent. Possesses neuroprotective properties. This is a controlled substance (stimulant)
Manufacturing ProcessTo 19.5 g (0.076 mol) of benzhydrylthioacetic acid in 110 ml of benzene was added drop by drop 19 ml of thionyl chloride. The mixture was refluxed 1 hour, benzene and the excess thionyl chloride was evaporated. A clear orange oil of benzhydrylthioacetyl chloride is obtained.
The benzhydrylthioacetyl chloride in 100 ml of methylene chloride was added drop by drop to 35 ml of ammonia in 40 ml of water. Once the addition is complete, the organic phase is washed with a dilute solution of soda and dried over Na2SO4, the solvent is evaporated and the residue is taken up in diisopropyl ether, the benzhydrylthioacetamide is crystallised. 16.8 g of product (yield 86%) are obtained. Melting point 110°C.
14.39 g (0.056) of benzhydrylthioacetamide are placed in a balloon flask and 60 ml of acetic acid and 5.6 ml of H2O2 are added. The mixture is left for one night at 40°C and about 200 ml of water are then added; the CRL 40476 crystallises. By recrystallisation from methanol 11.2 g of benzhydrylsulphinylacetamide are obtained. Yield: 73%, melting point 164- 166°C.
The synthesis of benzhydrylsulphinylacetamide (CRL 40476) on an industrial scale.
1.003 kg of thiourea is dissolved in 5.72 L of 48% hydrobromic acid and 0.880 L of water in a 20 L reaction vessel. The mixture is heated to 60°C and 2.024 kg of benzhydrol are introduced. The temperature is increased to 95°C and the contents of the vessel are allowed to cool to room temperature. The crystals are filtered off and washed with water. They are made into a paste again in 5.5 L of water and this is introduced into a 20 L reaction vessel with 3.5 L of soda lye (d = 1.33). The mixture is heated to 70°C and 1144 g of chloroacetic acid dissolved in 2.2 L of water are passed in slowly. After cooling the benzhydrylthioacetic acid is obtained, but is not isolated.
1.430 L of hydrogen peroxide are passed in over 3 hours at 30°C into the above reaction mixture. 22 L of water are then passed in, the insoluble material is filtered off and acidification is carried out with hydrochloric acid (d = 1.18). Filtration, washing with water to reform a paste and drying without heat are carried out. In this way, the benzhydrylsulphinylacetic acid is obtained.
The above acid is placed in a 20 L reaction vessel with 6 L of water. 1.1 liters of soda lye (d = 1.33) and 1.848 kg of sodium bicarbonate are added. 2.1 L of dimethyl sulfate are added. After one hour, crystallisation is induced. Filtration, drying without heat and washing are carried out. Methyl benzhydrylsulphinylacetate is obtained.
1 kg of methyl benzhydrylsulphinylacetate is dissolved in 3.5 liters of anhydrous methanol in a 10-liter balloon flask. NH3 is bubbled in at a high rate of flow for 1 hour, and then left in contact for 4 hours. Filtration, drying without heat and washing with water are then carried out. By recrystallisation from a mixture of water and methanol (4:1) and then from a mixture of water and methanol (9:1) and drying under reduced pressure, CRL 40476 is obtained in the form of a white crystalline powder; melting point 164-166°C. Total yield (calculated from the benzhydrol): 41%.
Brand nameProvigil (Cephalon);Modiodal.
Therapeutic FunctionPsychostimulant
General DescriptionModafinil (Provigil) has overall wakefulness-promotingproperties similar to those of central sympathomimetics. It isconsidered an atypical α1-norepinephrine (NE) receptorstimulant and is used to treat daytime sleepiness in narcolepsypatients. Adverse reactions at therapeutic doses arereportedly not severe and may include nervousness, anxiety,and insomnia. Modafinil is used by oral administration.
Biological ActivityPsychostimulant that displays neuroprotective and antiparkinsonian activity in a primate model of Parkinson's disease. Promotes vigilence and wakefulness without the central and peripheral side effects associated with conventional dopaminergic psychostimulants. Mechanism of action is not fully understood, possibly via modulation of catecholamine/GABAergic neurotransmission.
Tag:Modafinil(68693-11-8) Related Product Information
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