Etilamfetamine (trade names Apetinil and Adiparthrol; also known as ''N''-ethylamphetamine) 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 of the
phenethylamine
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amin ...
and
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 classes. It was invented in the early 20th century and was subsequently used as an
anorectic or
appetite suppressant in the 1950s, but was not as commonly used as other amphetamines such as
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 ...
,
methamphetamine
Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamph ...
, and
benzphetamine, and was largely discontinued once newer drugs such as
phenmetrazine were introduced. It most likely acts primarily as a dopamine releasing agent.
Its activity as a norepinephrine or serotonin releasing agent is not known.
Chemistry
The
molecular structure of ethylamphetamine is
analogous to
methamphetamine
Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamph ...
, with an
ethyl group
In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated ...
in place of the
methyl group.
[Amphetamine is a substituted phenethylamine with a methyl group at RA position.] It can also be considered a
substituted amphetamine
Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with sub ...
, with an ethyl group on the amphetamine backbone.
[The ]ethyl group
In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated ...
of ethylamphetamine is at RN position, hence the name ''N-ethylamphetamine''.[Ethylamphetamine is structurally similar to N-methylamphetamine (methamphetamine), the ]ethyl group
In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated ...
being replaced in methamphetamine with a methyl group.
Recreational Use
Ethylamphetamine can be used as a
recreational drug
Recreational drug use indicates the use of one or more psychoactive drugs to induce an altered state of consciousness either for pleasure or for some other casual purpose or pastime by modifying the perceptions and emotions of the user. When a ...
and, while its prevalence is less than amphetamine's, it is still encountered as a substance taken for recreational purposes.
Ethylamphetamine produces effects similar to amphetamine and methamphetamine, though it is of weaker
potency. At equipotent dosage, ethylamphetamine is subjectively less euphorigenic.
See also
*
3-Fluoroethamphetamine
3-Fluoroethamphetamine (3-FEA) is a stimulant drug of the amphetamine class which acts as a releasing agent of the monoamine neurotransmitters norepinephrine, dopamine and serotonin.
Compared to the unsubstituted ethylamphetamine, 3-fluoroethamp ...
*
Dimethylamphetamine
*
Fenfluramine
*
Isopropylamphetamine
Isopropylamphetamine is a psychostimulant of the substituted amphetamine class. It is an isomer of propylamphetamine and was discovered by a team at Astra Laekemedel AB. The isopropyl moiety reduces the stimulant activity of the compound but gre ...
*
Propylamphetamine
References
Notes
{{Phenethylamines
Substituted amphetamines
Anorectics
Norepinephrine-dopamine releasing agents