| Identification | More | [Name]
Modafinil | [CAS]
68693-11-8 | [Synonyms]
2-(BENZHYDRYLSULFINYL)ACETAMIDE
2-[(DIPHENYLMETHYL)SULFINYL]ACETAMIDE
AKOS BC-1794
MODAFINIL
MODAFINIL-DEA SCHEDULE IV
CRL-40476
Provigi
MODAFINIL INTERMEDIATE:DIPHENYL METHANESULFONYLACETAMIDE
Acetamide, 2-[(diphenylmethyl)sulfinyl]-
Modiodal
(Benzhydrylsulfinyl)acetamide | [EINECS(EC#)]
640-968-7 | [Molecular Formula]
C15H15NO2S | [MDL Number]
MFCD00868082 | [Molecular Weight]
273.35 | [MOL File]
68693-11-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [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
| [form ]
white solid | [pka]
14.88±0.40(Predicted) | [color ]
white
| [Usage]
A central nervous system vigilance promoting agent. Possesses neuroprotective properties. This is a controlled substance (stimulant) | [BCS Class]
4 | [CAS DataBase Reference]
68693-11-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [RIDADR ]
UN 1648 3 / PGII | [WGK Germany ]
3
| [HS Code ]
29309090 | [Hazardous Substances Data]
68693-11-8(Hazardous Substances Data) |
| Questions And Answer | Back Directory | [Description]
Marketed 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.
| [References]
https://en.wikipedia.org/wiki/Modafinil
http://bodyandhealth.canada.com/drug/getdrug/apo-modafinil
https://www.drugbank.ca/drugs/DB00745
|
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Originator]
Lafon (France) | [Uses]
A central nervous system vigilance promoting agent. Possesses neuroprotective properties. This is a controlled substance (stimulant) | [Uses]
ACE inhibitor, antihypertensive | [Uses]
Modafinil 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. | [Definition]
ChEBI: 2-[(diphenylmethyl)sulfinyl]acetamide is a sulfoxide that is dimethylsulfoxide in which two hydrogens attached to one of the methyl groups are replaced by phenyl groups, while one hydrogen attached to the other methyl group is replaced by a carbamoyl (aminocarbonyl) group. It is a sulfoxide and a monocarboxylic acid amide. | [Manufacturing Process]
To 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 name]
Provigil (Cephalon);Modiodal. | [Therapeutic Function]
Psychostimulant | [General Description]
Modafinil (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 Activity]
Psychostimulant 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. | [Clinical Use]
Excessive daytime drowsiness associated with narcolepsy
and obstructive sleep apnoea | [Drug interactions]
Potentially hazardous interactions with other drugs
Ciclosporin: reduced ciclosporin concentration.
Cytotoxics: concentration of bosutinib possibly
reduced - avoid.
Guanfacine: concentration of guanfacine possibly
reduced - avoid.
Oestrogens: metabolism accelerated (reduced
contraceptive effect).
Ulipristal: possibly reduces contraceptive effect of
ulipristal - avoid | [Metabolism]
Metabolised in the liver, partly by the cytochrome
P450 isoenzymes CYP3A4 and CYP3A5; two major
metabolites have been identified: acid modafinil and
modafinil sulfone, both of which are inactive.
Excretion is mainly through the kidneys. | [storage]
+4°C |
|