Phenylisobutylamine
Encyclopedia
Phenylisobutylamine, also known as α-ethylphenethylamine or AEPEA, is a stimulant
drug
of the phenethylamine
class. It is a higher homologue
of amphetamine
, differing from amphetamine's molecular structure only by the substitution of the methyl group at the alpha position
of the side chain
with an ethyl
group
. Compared to amphetamine, phenylisobutylamine has strongly reduced dopaminergic
effects, and instead acts as a selective
norepinephrine releasing agent
. The dextro
isomer
of phenylisobutylamine partially substitutes for dextroamphetamine
in rats.
A number of derivatives of phenylisobutylamine are known, including BDB, MBDB, EBDB, butylone (bk-MBDB), eutylone
(bk-EBDB), Ariadne
(α-Et-DOM), 4-CAB
, and 4-MAB
.
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
of the phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
class. It is a higher homologue
Homologous series
In chemistry, a homologous series is a series of compounds with a similar general formula, possessing similar chemical properties due to the presence of the same functional group, and showing a gradation in physical properties as a result of increase in molecular size and mass...
of amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
, differing from amphetamine's molecular structure only by the substitution of the methyl group at the alpha position
Alpha carbon
The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
of the side chain
Side chain
In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called "main chain" or backbone. The placeholder R is often used as a generic placeholder for alkyl group side chains in chemical structure diagrams. To indicate other non-carbon...
with an ethyl
Ethyl
Ethyl may refer to:* Ethyl group, a functional group in organic chemistry* Ethyl Corporation, a fuel additive company* Ethanol, also known as ethyl alcohol* Cold Ethyl, a rock band founded by Nicke Andersson...
group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
. Compared to amphetamine, phenylisobutylamine has strongly reduced dopaminergic
Dopaminergic
Dopaminergic means related to the neurotransmitter dopamine. For example, certain proteins such as the dopamine transporter , vesicular monoamine transporter 2 , and dopamine receptors can be classified as dopaminergic, and neurons which synthesize or contain dopamine and synapses with dopamine...
effects, and instead acts as a selective
Binding selectivity
Binding selectivity refers to the differing affinities with which different ligands bind to a substrate forming a complex. A selectivity coefficient is the equilibrium constant for the reaction of displacement by one ligand of another ligand in a complex with the substrate...
norepinephrine releasing agent
Norepinephrine releasing agent
A norepinephrine releasing agent is a type of drug which induces the release of norepinephrine and epinephrine from the pre-synaptic neuron into the synapse...
. The dextro
Dextro
Dextro is the pseudonym given to the Scottish Falkirk born DIY musician, Ewan Mackenzie. Under the Dextro moniker he has released a number of works, most notably the albums Winded , Consequence Music and the 12" single Do You Need Help...
isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
of phenylisobutylamine partially substitutes for dextroamphetamine
Dextroamphetamine
Dextroamphetamine is a psychostimulant drug which is known to produce increased wakefulness and focus as well as decreased fatigue and decreased appetite....
in rats.
A number of derivatives of phenylisobutylamine are known, including BDB, MBDB, EBDB, butylone (bk-MBDB), eutylone
Eutylone
β-Keto-Ethylbenzodioxolylbutanamine is a stimulant compound developed in the 1960s, which has been reported as a novel designer drug.- See also :* Butylone* EBDB* Ethylone* MDEA* Pentylone...
(bk-EBDB), Ariadne
Ariadne (psychedelic)
Ariadne , or 4-methyl-2,5-dimethoxy-alpha-ethylphenethylamine, is a lesser-known psychedelic drug. It is a homologue of 2C-D and DOM. Ariadne was first synthesized by Alexander Shulgin...
(α-Et-DOM), 4-CAB
4-Chlorophenylisobutylamine
4-Chlorophenylisobutylamine , also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine class...
, and 4-MAB
4-Methylphenylisobutylamine
4-Methylphenylisobutylamine , also known as 4-methyl-α-ethylphenethylamine, is a stimulant drug of the phenethylamine class.- References :...
.