Introduction to Phenethylamines

Phenethylamines are a wide class of compounds derived from phenethylamine. It is the substitutions made to this Phenethylamine molecule that result in the new molecules that propagate the category collectively known as The Phenethylamines, sometimes referred to as Substituted Phenethylamines.

Phenethylamines are the biggest class of psychoactive compounds, and can exhibit a wide spectrum of effects. Phenethylamines can be psychedelic (mescaline, 2C-B, TMA), entactogen (MDMA), stimulant (amphetamine, methamphetamine). Although some phenethylamines have only one type of effect (for example amphetamine is only stimulant), many have effects which are a mix of different "main" effects, justifying the term "spectrum" for the effects of phenethylamines.

Two notable subcategories of phenethylamines are amphetamines and methamphetamines.

Chemical description of Phenethylamines

Phenethylamines are based on the parent compound phenethylamine, which in turn is analoguous to the amino acid phenylalanine.

The structural formula of any substituted phenethylamine contains a phenyl ring that is joined to an amino (NH) group via a two-carbon sidechain. Hence, any substituted phenethylamine can be classified according to the substitution of hydrogen (H) atoms on phenethylamine's phenyl ring, sidechain, or amino group with a specific group of atoms.

Uses of Phenethylamines

Most phenethylamines are used recreatively, and are thus controlled if not illegal to possess, produce or sell.

Phenethylamine is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, in orally ingested phenethylamine, a significant amount is metabolized in the small intestine by monoamine oxidase B (MAO-B) and then aldehyde dehydrogenase (ALDH), which convert it to phenylacetic acid. This means that for significant concentrations to reach the brain, the dosage must be higher than for other methods of administration.

Phenethylamines, or more properly, substituted phenethylamines, are the group of phenethylamine derivatives that contain phenethylamine as a "backbone"; in other words, this chemical class includes derivative compounds that are formed by replacing one or more hydrogen atoms in the phenethylamine core structure with substituents. The class of substituted phenethylamines includes all substituted amphetamines, and substituted methylenedioxyphenethylamines (MDxx), and contains many drugs which act as empathogens, stimulants, psychedelics, anorectics, bronchodilators, decongestants, and/or antidepressants, among others.

Effects of Phenethylamines

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 amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons; to a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentatio

General pharmacology of Phenethylamines

Phenethylamine, being similar to amphetamine in its action at their common biomolecular targets, releases norepinephrine and dopamine. Phenethylamine also appears to induce acetylcholine release via a glutamate-mediated mechanism.

Phenethylamine has been shown to bind to human trace amine-associated receptor 1 (hTAAR1) as an agonist.

Dangers of Phenethylamines

Sources of Phenethylamines

Natural sources

Phenethylamine is produced by a wide range of species throughout the plant and animal kingdoms, including humans; it is also produced by certain fungi and bacteria (genera: Lactobacillus, Clostridium, Pseudomonas and the family Enterobacteriaceae) and acts as a potent antimicrobial against certain pathogenic strains of Escherichia coli (e.g., the O157:H7 strain) at sufficient concentrations.

Synthesis

Phenethylamine is a primary amine, the amino-group being attached to a benzene ring through a two-carbon, or ethyl group. It is a colourless liquid at room temperature that has a fishy odor, and is soluble in water, ethanol and ether. Its density is 0.964 g/ml and its boiling point is 195 °C. Upon exposure to air, it combines with carbon dioxide to form a solid carbonate salt. Phenethylamine is strongly basic, pKb = 4.17 (or pKa = 9.83), as measured using the HCl salt, and forms a stable crystalline hydrochloride salt with a melting point of 217 °C.

Substituted derivatives
Substituted phenethylamines are a chemical class of organic compounds based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents

Legal Status of Phenethylamines

AU: Unscheduled
CA: Unscheduled
UK: Unscheduled
US: Unscheduled
UN: Unscheduled

History of Phenethylamines

Insights for Phenethylamines

Phenethylamines

More Phenethylamines Sections and Information

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Phenethylamine research chemicals:

Related categories

Amphetamines, Methamphetamines, Catecholamines

References