68693-11-8 Usage
Description
Modafinil is a central nervous system (CNS) stimulant that is marketed as a wakefulness promoting agent. It 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. Additionally, recent studies have shown that modafinil may be effective in helping cocaine addicts fight against their addiction. The sleepiness-preventing effects of modafinil function by stimulating certain parts of the brain, activating neurons and binding to the dopamine reuptake pump to inhibit the reuptake of dopamine, thus preventing drowsiness and keeping people awake.
Uses
Used in Sleep Disorder Treatment:
Modafinil is used as a wakefulness promoting agent for the treatment of narcolepsy, obstructive sleep apnea, hypopnea syndrome, shift-work sleep disorder, and circadian rhythm sleep disorder. It helps reduce excessive daytime sleepiness and improves the patient's ability to stay awake and alert.
Used in Neurological Disorders:
Modafinil is used as a psychostimulant that displays neuroprotective and antiparkinsonian activity in a primate model of Parkinson's disease. It has been reported to exhibit minimal peripheral side effects at therapeutic doses and appears to have low abuse potential.
Used in Cerebral Infarction and Ischemia Treatment:
Modafinil is used in the treatment of cerebral infarction and ischemia, as it has been claimed to have beneficial effects on these conditions.
Used in Drug Addiction Treatment:
Modafinil is used as an aid for cocaine addicts to fight against their addiction, as recent studies have shown its potential effectiveness in this area.
Used in Neuroprotection:
Modafinil is used as a central nervous system vigilance promoting agent that possesses neuroprotective properties, helping to protect the brain from damage and degeneration.
Note: Modafinil is a controlled substance (stimulant) and should be used under the guidance of a healthcare professional.
References
https://en.wikipedia.org/wiki/Modafinil
http://bodyandhealth.canada.com/drug/getdrug/apo-modafinil
https://www.drugbank.ca/drugs/DB00745
Originator
Lafon (France)
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%.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 68693-11-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,8,6,9 and 3 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 68693-11:
(7*6)+(6*8)+(5*6)+(4*9)+(3*3)+(2*1)+(1*1)=168
168 % 10 = 8
So 68693-11-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)/t19-/m1/s1
68693-11-8Relevant articles and documents
Spectroscopic and molecular modeling methods to investigate the interaction between psycho-stimulant modafinil and calf thymus DNA using ethidium bromide as a fluorescence probe
Akbay, Nuriye,Koksal, Zeynep,Oguzcan, Esra,Taskin-Tok, Tugba,Uzgoren-Baran, Ayse
, (2022/01/08)
Interaction type of modafinil with calf thymus DNA (ct-DNA) was examined systematically using ethidium bromide (EB) as a fluorescence probe by fluorescence spectroscopy, UV–Vis spectroscopy, viscosity and molecular docking method. The fluorescence quenchi
Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation
Liu, Shengping,Jin, Shengnan,Wang, Hao,Qi, Zaojuan,Hu, Xiaoxue,Qian, Bo,Huang, Hanmin
, (2021/03/15)
A nickel-catalyzed oxidative dehydrogenative coupling reaction of alkane with thiol for the construction of C(sp3)-S bond has been established, affording more than 50 alkyl thioethers. Notably, pharmaceutical and agrochemicals, such as Provigil, Chlorbenside and Pyridaben, were readily synthesized by this approach. The sterically hindered ligand BC and disulfide which was formed in situ oxidation of thiol, efficiently avoiding nickel-catalyst poisoning. A set of mechanistic experiments disclose both Ni-catalyzed and Ni-free HAA processes.
Alloxan-catalyzed biomimetic oxidations with hydrogen peroxide or molecular oxygen
Zhang, Shiqi,Li, Guangxun,Li, Ling,Deng, Xiongfei,Zhao, Gang,Cui, Xin,Tang, Zhuo
, p. 245 - 252 (2019/12/24)
Inspired by biological flavin catalysis, the nonionic alloxan derivatives were applied as the biomimetic catalysts for various oxidations, catalyzing oxidations of sulfides and amines with hydrogen peroxide or molecular oxygen under mild conditions with high yields in a short time. The whole catalytic cycle has been verified to be a biomimetic approach through the formation of the alloxan hydroperoxide reactive intermediate. Additionally, encouraging asymmetric catalytic results have been obtained with an easily prepared chiral alloxan in a sulfoxidation reaction.
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