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Armodafinil

CAS No.
112111-43-0
Chemical Name:
Armodafinil
Synonyms
Nuvigil;CRL 40982;CEP 10952;R MODAFINIL; Armodafinil;Modafinil R-Isomer;Armodafinil CIV (500 mg);2-[(R)-benzhydrylsulfinyl]acetamide;(R)-2-(benzhydrylsulfinyl)acetamide;2-[(R)-(Diphenylmethyl)sulfinyl]-acetamide
CBNumber:
CB3500844
Molecular Formula:
C15H15NO2S
Molecular Weight:
273.35
MDL Number:
MFCD09841055
MOL File:
112111-43-0.mol
Last updated:2023-06-08 09:03:01

Armodafinil Properties

Melting point 156-1580C
Boiling point 559.1±50.0 °C(Predicted)
Density 1.283
storage temp. Controlled Substance, -20°C Freezer
solubility DMSO: ≥16mg/mL
pka 14.88±0.40(Predicted)
form powder
color white to tan
optical activity [α]/D -15 to -20° in methanol (C=1)
NCI Dictionary of Cancer Terms armodafinil; Nuvigil
FDA UNII V63XWA605I
NCI Drug Dictionary armodafinil
ATC code N06BA13

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H361d
Precautionary statements  P202-P264-P270-P280-P301+P312-P308+P313
Hazard Codes  Xi
Risk Statements  41
Safety Statements  26-39
WGK Germany  3
NFPA 704
0
3 0

Armodafinil Chemical Properties,Uses,Production

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

Used for treatment of excessive sleepiness, a1-adrenoceptor agonist

Uses

analeptic

Uses

Used for treatment of excessive sleepiness, α1-adrenoceptor agonist.

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.

Armodafinil Preparation Products And Raw materials

Raw materials

Preparation Products

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 (R)-2-(benzhydrylsulfinyl)acetamide 2-[(R)-benzhydrylsulfinyl]acetamide Modafinil R-Isomer ArmodafinilQ: What is Armodafinil Q: What is the CAS Number of Armodafinil Q: What is the storage condition of Armodafinil Q: What are the applications of Armodafinil R-Modafinil D10Q: What is R-Modafinil D10 Q: What is the CAS Number of R-Modafinil D10 Q: What is the storage condition of R-Modafinil D10 Q: What are the applications of R-Modafinil D10 Armodafinil CIV (500 mg) *Buprenorphine Impurity 5 (Buprenorphine EP Impurity E) 112111-43-0 NUVIGIL Chiral Reagents Intermediates & Fine Chemicals Neurochemicals Pharmaceuticals