Armodafinil

Base Information

• Chemical Name: Armodafinil
• CAS No.: 112111-43-0
• Molecular Formula: C15H15NO2S
• Molecular Weight: 273.356
• European Community (EC) Number: 682-508-8
• UNII: V63XWA605I
• DSSTox Substance ID: DTXSID90920667
• Wikipedia: Armodafinil
• Wikidata: Q418913
• NCI Thesaurus Code: C65241
• RXCUI: 641465
• Pharos Ligand ID: YGT27K9BRV74,YGT7GHB8X5V7
• Metabolomics Workbench ID: 149768
• ChEMBL ID: CHEMBL1201192
• Mol file: 112111-43-0.mol

Synonyms:2 Benzhydrylsulfinylacetamide;2-((diphenylmethyl)sulfinyl)acetamide;2-((R)-(diphenylmethyl)sulfinyl)acetamide;2-(Benzhydrylsulfinyl)acetamide;2-Benzhydrylsulfinylacetamide;Alertec;armodafinil;benzhydrylsulfinylacetamide;CRL 40476;CRL-40476;modafinil;Modiodal;Nuvigil;Provigil;R Modafinil;R-modafinil;Sparlon

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Armodafinil

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.56E-12mmHg at 25°C
• Melting Point: 156-158 °C
• Refractive Index: 1.645
• Boiling Point: 559.1 °C at 760 mmHg
• PKA: 14.88±0.40(Predicted)
• Flash Point: 292 °C
• PSA: 79.37000
• Density: 1.283 g/cm³
• LogP: 3.57600
• Storage Temp.: Controlled Substance, -20?C Freezer
• Solubility.: DMSO: ≥16mg/mL
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 273.08234989
• Heavy Atom Count: 19
• Complexity: 302

Purity/Quality:

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)N
• Isomeric SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)[S@](=O)CC(=O)N
• Recent ClinicalTrials: Single Agent Armodafinil for Patient-Reported Fatigue Following Radiation Therapy for Head and Neck Cancer
• Recent EU Clinical Trials: A Randomized, Open-Label Study to Characterize the Pharmacokinetics, Pharmacodynamics, and Safety of Single and Multiple Doses of Armodafinil (50, 100, and 150 mg/day) in Children and Adolescents with Excessive Sleepiness Associated With Narcolepsy
• 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.
• Uses: Used for treatment of excessive sleepiness, a1-adrenoceptor agonist Used for treatment of excessive sleepiness, α1-adrenoceptor agonist. analeptic

Technology Process of Armodafinil

There total 42 articles about Armodafinil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-(diphenylmethylthio)acetamide (68524-30-1) → Modafinil (112111-43-0,112111-47-4,112111-49-6,68693-11-8)

Guidance literature:

With phthaloyl peroxide; In dichloromethane; at 25 ℃; for 8h; chemoselective reaction; Schlenk technique;

DOI:10.1039/c7ob00021a

Reference yield: 95.73%

2-(diphenylmethylthio)acetamide (68524-30-1) → Modafinil (112111-43-0,112111-47-4,112111-49-6,68693-11-8) + Modafinil sulfone

Guidance literature:

With dihydrogen peroxide; In acetic acid; at 40 ℃; for 6h;

Reference yield: 95.0%

(diphenylmethyl)(ethyl acetate)sulfoxide (118286-19-4) → Modafinil (112111-43-0,112111-47-4,112111-49-6,68693-11-8)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 12h; Inert atmosphere;

upstream raw materials:

2-(diphenylmethylthio)acetamide

modafinil acid

1,1-Diphenylmethanol

(benzhydrylthio)acetic acid

Downstream raw materials:

C₂₀H₁₉NO₅S

C₁₉H₁₇NO₅S

2-[(R)-(diphenylmethyl)sulfinyl]acetamide monohydrate

Refernces

• 1、 Hartman, Tomá?,?turala, Ji?í,Cibulka, Radek. "Two-Phase Oxidations with Aqueous Hydrogen Peroxide Catalyzed by Amphiphilic Pyridinium and Diazinium Salts". . p. 3573 - 3586. Retrieved 2015.
• 2、 Cuéllar, Elena,Diez-Varga, Alberto,Torroba, Tomás,Domingo-Legarda, Pablo,Alemán, José,Cabrera, Silvia,Martín-Alvarez, Jose M.,Miguel, Daniel,Villafa?e, Fernando. "Luminescent cis-Bis(bipyridyl)ruthenium(II) Complexes with 1,2-Azolylamidino Ligands: Photophysical, Electrochemical Studies, and Photocatalytic Oxidation of Thioethers". . p. 7008 - 7022. Retrieved 2021.
• 3、 Maurya, Shivam,Yadav, Dhiraj,Pratap, Kemant,Kumar, Atul. "Efficient atom and step economic (EASE) synthesis of the "smart drug" Modafinil". . p. 629 - 633. Retrieved 2017.
• 4、 Ternois, James,Guillen, Frederic,Plaquevent, Jean-Christophe,Coquerel, Gerard. "Asymmetric synthesis of modafinil and its derivatives by enantioselective oxidation of thioethers: comparison of various methods including synthesis in ionic liquids". . p. 2959 - 2964. Retrieved 2007.
• 5、 Akbay, Nuriye,Koksal, Zeynep,Oguzcan, Esra,Taskin-Tok, Tugba,Uzgoren-Baran, Ayse. "Spectroscopic and molecular modeling methods to investigate the interaction between psycho-stimulant modafinil and calf thymus DNA using ethidium bromide as a fluorescence probe". . . Retrieved 2022/01/08.
• 6、 Liu, Shengping,Jin, Shengnan,Wang, Hao,Qi, Zaojuan,Hu, Xiaoxue,Qian, Bo,Huang, Hanmin. "Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation". supporting information. . Retrieved 2021/03/15.