Armodafinil Property

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)

Safety

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

Armodafinil Chemical Properties,Usage,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

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

Uses

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.