Adrafinil Crystal


adrafinil


Chemical Data :

IUPAC: (±)-2-Benzhydrylsulfinylethanehydroxamic acid

CAS: 63547-13-7

ChemSpider:2297976

Molecular Weight: 289.351 g/mol

Molecular Formula: C15H15NO3S

 

Adrafinil Profile

Adrfinil is a wakefulness promoting drug or “eugeroic” that was previously marketed in France as a medicine particularly for the elderly in order to increase wakefulness, attention and mood. Off-label the drug was used by people wishing to avoid the effects of fatigue such as night workers and people who needed to stay awake and alert for prolonged periods of time. It is considered by many to be a nootropic agent – in other words a drug which may be beneficial for thinking, study and attention in those wishing to enhance their cognition or study longer or better.

It is a prodrug that is metabolised at the liver to the popular eugoric agent known as modafinil. It is only after metabolism to modafinil that the compound is active, thus giving adrafinil a similar pharmacological range of effects to modafinil.

It was first discovered in 1974 by chemists working at the French pharmaceutical firm Lafon Laboritories whilst they were screening potential compounds for a new analgesic. However instead of showing analgesic effects in experiment adrafinil induced hyperactivity and wakefulness in animals typical of the effects of a psycho-stimulant. It was trialled for the treatment of narcolepsy in 1977 and reached the marked as a narcolepsy treatment in 1985.

The effects of adrafinil take a little longer to materialise as it must first be metabolised to its active form. This gives it a slower onset of action than modafinil, with adrafinil typically taking 45-60 minutes to take effect after being taken on an empty stomach.

Adrafinil was sold in France under the brand name Olmifon until it was voluntarily removed sale.

Adrafinil has the formal and systematic IUPAC name (±)-2-Benzhydrylsulfinylethanehydroxamic acid. It has a molar mass of 289.351 grams and empirical formula C15H15NO3S. It has an oral bioavailability of 80 %, is metabolised primarily at the liver and excreted by the renal route. It has a biological half life of one hour with its primary metabolite modafinil having a half life of 12 – 15 hours.

Adrafinil is said to have a greater specificity of action and a reduced incidence of side effects when compared to modafinil. This includes a reduced reportage of side effects like stomach pain, skin irritation, anxiety and elevated liver enzymes.

One case report which has been published claims that adrafinil may increase sexual urges and interest.

There is another case report of adrafinil inducing orofacial dystonia. This has also been reported in modafinil. This is an involuntary movement of the facial muscles and may present an alarming side effect in people taking adrafinil.

It was previously reported as being an α1-adrenergic receptor agonist due to the blocking effects of α1-adrenergic receptor antagonists.  However adrafinil has not been shown to bind to the alpha 1 receptor in vitro. Adrafinil also lacks the sympathomimetic side effects that would be present with a drug binding to the alpha adrenergic receptor. It was found in 2009 that modafinil acts as a weak but atypical dopamine reuptake inhibitor. It is now thought that this interaction explains its pharmacological effects.