Clobenzorex (Asenlix, Dinintel, Finedal, Rexigen) is a

stimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

of the

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classificat ...

used as an

appetite suppressant An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic. The term is (from the Greek ''ἀν-'' (an-) = "without" and ...

. The drug is legally distributed in

Mexico Mexico (Spanish: México), officially the United Mexican States, is a country in the southern portion of North America. It is bordered to the north by the United States; to the south and west by the Pacific Ocean; to the southeast by Guatema ...

under the trade name Asenlix by

Aventis Sanofi S.A. is a French multinational pharmaceutical and healthcare company headquartered in Paris, France. Originally, the corporation was established in 1973 and merged with Synthélabo in 1999 to form Sanofi-Synthélabo. In 2004, Sanofi-Syn ...

. Chemically, clobenzorex is an ''N''-substituted amphetamine

prodrug A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...

that is converted to ''d''-amphetamine soon after ingestion. In commercial production, clobenzorex is supplied in 30 mg doses as the hydrochloride salt in green-tinted capsules. The drug gained use as a prescription anorectic in the 1970s. In the United States, clobenzorex tablets (among other varieties of stimulants, such as amphetamine) have been used by athletes who ingest the drug to reduce fatigue, increase attention, and improve reaction times during athletic activities. The green-tinted Asenlix capsules (generic forms can be seen as half light green, half dark green capsules marked "IFA") are known as "greenies" among US baseball players, a slang term that in current use has expanded to generically refer to any amphetamine class stimulant. Yet, Clobenzorex is not controlled within the United States or subject to import controls. Importation of Clobenzorex for personal use is lawful provided that is for use to treat a condition with no approved medications, unlawful marketing is not occurring in the U.S, not deemed hazardous to health for the treating the condition, and is verified as a continuation of a treatment plan that began in a foreign country.

Synthesis

Condensation between

(1) and 2-chlorobenzaldehyde (2) gives a

Schiff-base In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines#Nomenclature and classi ...

CID:135056236
(3). Subsequent reduction with

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds appli ...

completed the synthesis of clobenzorex (4). Apparently, also made from the acid chloride, and reduction of the amide with lithium aluminium anhydride.

References

{{Phenethylamines Anorectics Substituted amphetamines Prodrugs Chloroarenes Norepinephrine-dopamine releasing agents

Synthesis

See also

References