112111-43-0

Basic information

• Product Name: R MODAFINIL
• Synonyms: R MODAFINIL; Armodafinil;2-[(R)-(Diphenylmethyl)sulfinyl]-acetamide;CEP 10952;CRL 40982;Nuvigil;AcetaMide,2-[(R)-(diphenylMethyl)sulfinyl]-;2-[(R)-(Diphenylmethyl)sulfinyl]-acetamide, CEP 10952, CRL 40982, Nuvigil
• CAS NO: 112111-43-0
• Molecular Formula: C₁₅H₁₅NO₂S
• Molecular Weight: 273.354
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals;NUVIGIL
• Mol File: 112111-43-0.mol
• Article Data: 51

Chemical Properties

• Melting Point: 156-1580C
• Boiling Point: 559.1 °C at 760 mmHg
• Flash Point: 292 °C
• Appearance: white to tan/
• Density: 1.283
• Vapor Pressure: 1.56E-12mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Controlled Substance, -20?C Freezer
• Solubility: DMSO: ≥16mg/mL
• PKA: 14.88±0.40(Predicted)
• CAS DataBase Reference: R MODAFINIL(CAS DataBase Reference)
• NIST Chemistry Reference: R MODAFINIL(112111-43-0)
• EPA Substance Registry System: R MODAFINIL(112111-43-0)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 112111-43-0(Hazardous Substances Data)

Usage

Description

Armodafinil, an α1-adrenoceptor agonist, was launched for the oral treatment of excessive sleepiness associated with narcolepsy, SWSD, and obstructive sleep apnea/hypopnea syndrome (OSA). It is the R-enantiomer of modafinil, which is a previously marketed wake-promoting agent. The key differentiator for armodafinil is its longer pharmacokinetic half-life as compared with the S-enantiomer (10-14 hvs.3-4h). At therapeutic concentrations, armodafinil does not bind to most of the potentially relevant receptors for sleep/wake regulation (e.g., serotonin, dopamine, and adenosine receptors) or transporters of neurotransmitters or enzymes involved in sleep/wake regulation (e.g., serotonin, norepinephrine, and phosphodiesterase VI transporters). Both armodafinil and modafinil block dopamine reuptake by binding to the dopamine transporter and increasing dopamine concentrations in certain regions of the brain. However, dopamine receptor antagonists (e.g., haloperidol) and dopamine synthesis inhibitors (e.g., α-methyl-p-tyrosine) do not block modafinil’s action.In addition to its wake-promoting effects and ability to increase locomotor activity in animals, modafinil produces psychoactive and euphoric effects, alterations in mood, perception, thinking, and feelings typical of other CNS stimulants in humans. Modafinil was also partially discriminated as stimulant-like. However, the potential for abuse and dependency appears to be lower for modafinil than amphetamine-like stimulants.The most common adverse events associated with armodafinil included headache, nausea, dizziness, and insomnia.

Chemical Properties

White Solid

Originator

Cephalon (US)

Uses

Different sources of media describe the Uses of 112111-43-0 differently. You can refer to the following data:
1. Used for treatment of excessive sleepiness, a1-adrenoceptor agonist
2. Used for treatment of excessive sleepiness, α1-adrenoceptor agonist.
3. analeptic

Definition

ChEBI: A 2-[(diphenylmethyl)sulfinyl]acetamide that has R configuration at the sulfur atom. Like its racemate, modafinil, it is used for the treatment of sleeping disorders such as narcolepsy, obstructive sleep apnoea, and shift-work sleep disord r. Peak concentration in the blood later occurs later following administration than with modafinil, so it is thought that armodafinil may be more effective than modafinil in treating people with excessive daytime sleepiness.

Brand name

Nuvigil

Synthesis

Armodafinil can be obtained starting from (+)-2( diphenylmethylsulfinyl)acetic acid via optical resolution using S-(-)-amethylbenzylamine, followed by esterification to the methyl ester and subsequent amidation with ammonium hydroxide. It can also be derived enantioselectively from 2-(diphenylmethylthio)acetamide via asymmetric oxidation with cumene hydroperoxide and titanium isopropoxide-S,Sdiethyl tartrate complex.

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)

Upstream product

• 63547-22-8 (benzhydrylthio)acetic acid 
• 91-01-0 1,1-Diphenylmethanol 
• 68524-29-8 benzhydrylsulfanyl acetyl chloride 
• 63547-24-0 modafinil acid 
• 68524-30-1 2-(diphenylmethylthio)acetamide 
• 118286-24-1 methyl diphenylmethylmercaptoacetate 
• 776-74-9 Bromodiphenylmethane 
• 713134-72-6 (R)-(-)-methyl (diphenylmethanesulfinyl)-acetate 
• 118286-19-4 (diphenylmethyl)(ethyl acetate)sulfoxide 
• 63547-23-9 (diphenylmethyl)(ethyl acetate)sulfide 
• 112111-45-2 (R)-Modafinil acid 
• 827603-84-9 2-((R)-Diphenyl-methanesulfinyl)-1-((R)-4-phenyl-2-thioxo-thiazolidin-3-yl)-ethanone 
• 101-81-5 Diphenylmethane 
• 90-99-3 diphenylchloromethane 

Downstream Products

• 947318-12-9 2-[(R)-(diphenylmethyl)sulfinyl]acetamide monohydrate 
• 1502873-99-5 C₂₀H₁₉NO₅S 
• 1502874-00-1 C₁₉H₁₇NO₅S 

Relevant articles and documents

Vanadium–Schiff base complex-functionalized SBA-15 as a heterogeneous catalyst: synthesis, characterization and application in pharmaceutical sulfoxidation of sulfids

VO2(picolinichydrazone) complex as a catalyst was stabilized on a SBA-15 mesoporous silica as a catalytic support by using (3-chloropropyl)triethoxysilane as a connector. SBA-15 is nanoporous and has a high ratio of surface area to volume. The immobilization of a metal–Schiff base complex to the surface area of SBA-15 can improve its catalytic effects by increasing the catalytic surface area. Unlike homogeneous catalysts, heterogeneous catalysts can be recovered and reused several times without any significant loss of catalytic activity. A vanadium–Schiff base complex-functionalized SBA-15 was synthesized by covalency connected by a pre-synthesised VO2(picolinichydrazone) complex to silanated SBA-15. The synthesized vanadium–Schiff base complex was characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, carbon nuclear magnetic resonance (13C NMR) spectroscopy and Fourier transform infrared spectroscopy (FT-IR), and the final V/SBA-15 was characterized by FT-IR, ultraviolet–visible spectrophotometry and X-ray powder diffraction. The morphology of V/SBA-15 was also obtained by scanning electron microscopy and transmission electron microscopy. The catalytic effect was examined by using V/SBA-15 as a heterogeneous catalyst in sulfoxidation reactions. The synthesis of modafinil and modafinic acid by pharmaceutical sulfoxidation of solfides was carried out and the effects of different solvents, reaction times and also recoverability and reusability of the heterogeneous catalyst were investigated. This catalyst showed high yield of sulfide conversion, stability and recyclability in the sulfoxidation of sulfides.

New synthetic route to modafinil drug including desulfobenzhydrylation of sodium carbamoylmethyl thiosulfate: Experimental and quantum chemical studies

A new synthetic route to 2-benzhydrylsulfinylacetamide (1), a nootropic drug modafinil, is described. The synthesis includes the alkylation of sodium thiosulfate with chloroacetamide to sodium carbamoylmethyl thiosulfate, the desulfobenzhydrylation of the latter by benzhydrol in formic acid to form benzhydrylthioacetamide (3a), and the further oxidation of this thioamide with hydrogen peroxide. According to B3LYP/6-31G** DFT calculations, the key step of the synthesis, namely, desulfobenzhydrylation of salt 6a, occurs only insignificantly due to the energetically unfavorable direct attack of this salt by benzhydryl formate; the reaction mainly involves the attack by the benzhydrilium carbocation Ph2CH+. The oxidation of sulfide 3a to sulfinylacetamide 1 is efficiently catalyzed by side proton-donor molecules (constituents of the transition states of the reaction). The oxidant can be the anionic form of the reactant (HO2- ion), which reacts with sulfide 3a via the unusual noncatalytic mechanism. At the step of transition state formation, this mechanism resembles the S N2 substitution.

Self-repairing metal-organic hybrid complexes for reinforcing immobilized chloroperoxidase reusability

A self-repairing metal-enzyme hybrid nanocatalyst with a sodium alginate (SA) coating was reported in this study. Compared with free CPO, immobilized chloroperoxidase (CPO) has similar Km and Kcat values. SA-coated CPO@Ca3

Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil

A highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid was achieved employing the fungus Beauveria bassiana in very good yield. This product was amidated using the bacteria Bacillus subtilis to afford (S)-modafinil in good yield.

One-pot parallel synthesis of alkyl sulfides, sulfoxides, and sulfones

A simple and cost-effective one-pot parallel synthesis approach to sulfides, sulfoxides, and sulfones from thiourea was elaborated. The method combines two procedures optimized to the parallel synthesis conditions: alkylation of thiourea with alkyl chlorides and mono or full oxidation of in situ generated sulfides with H2O2 or H2O2-(NH4)2MoO4. The experimental set up required commonly used lab equipment: conventional oven and ultrasonic bath; the work up includes filtration or extraction with chloroform. The method was evaluated on an 81 member library of drug-like sulfides, sulfoxides, and sulfones yielding the compounds on a 30-300 mg scale. A small-scale synthesis of 2-(benzhydrylsulfinyl)acetamide (modafinil) utilizing our approach resulted in similar efficiency to the published procedures.

Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation

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.

Preparation of asymmetric phase-transfer catalyst, 1,4-bis((4s,5s)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium chloride

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