2-MDP (U-23807A) is a
dissociative
Dissociatives, colloquially dissos, are a subclass of hallucinogens that distort perception of sight and sound and produce feelings of detachment – dissociation – from the environment and/or self. Although many kinds of drugs are capable of ...
anaesthetic
An anesthetic (American English) or anaesthetic (British English; see spelling differences) is a drug used to induce anesthesia — in other words, to result in a temporary loss of sensation or awareness. They may be divided into t ...
drug which has been found to be an
NMDA antagonist
NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the ''N''-Methyl-D-aspartate receptor ( NMDAR). They are commonly used as anesthetics for humans and animals; the state of anesthesia they ind ...
and produces similar effects to
PCP in animals. The ''levo'' or (−)-
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
is the active form of the drug.
It also has
stimulant
Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...
effects, having only around one third the potency of
amphetamine
Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...
by weight, but with a long duration of action, lasting more than 24 hours from a single oral dose.
Effects
The therapeutic action is said to exhibit appetite suppressant- and antidepressant-like activity.
Synthesis
In a variation of the nitrile-aldol reaction, combination of
benzophenone
Benzophenone is a naturally occurring organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. It is a white solid with a low melting point and ros ...
(1) and
propionitrile
Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to oth ...
(2), in the presence of
sodamide base and
ethyl ether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs to the ether class of o ...
solvent, leads to 3-hydroxy-2-methyl-3,3-diphenylpropanenitrile (3).
The reduction of the intermediate nitrile group with
lithium aluminium hydride
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...
completes the synthesis of 2-MDP (4).
References
{{Ionotropic glutamate receptor modulators
Dissociative drugs
Stimulants