Etilamphetamine
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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