The organic compound, trace amine and natural monoamine alkaloid phenethylamine (PEA), acts as a central nervous stimulant in the human brain. Phenethylamine in the brain regulates monoamine neurotransmission through binding to trace amine-associated receptor 1 (TAAR1), and inhibiting vesicular monoamine transporter 2 (2 (VMAT2)) in monoamine neurons. It also functions as a neurotransmitter within the human central nervous system to a lesser degree. Phenethylamine, which is made from L-phenylalanine in mammals, can be produced by the enzyme aromatic L-amino acid decarboxylase via an enzyme-enzymatic decarboxylation. Phenethylamine can also be found in other organisms and foods after microbial fermentation.
Phenethylamine can be used as a dietary supplement to improve mood and weight loss. However, significant amounts of phenethylamine are metabolized in small intestines by monoamine oxidase-B (MAO-B), and then aldehyde-dehydrogenase- (ALDH), where it is converted into phenylacetic acids. The dosage of phenethylamine must be greater than that used for other administration methods in order to reach the brain in significant amounts. It is believed to play a role in falling in love. However, it has not been supported by any evidence.
Substituted phenethylamines or phenethylamines are a group of phenethylamine derivatives that contain phenethylamine “backbone”. This chemical class also includes derivative compounds formed by substituting one or more hydrogen atoms from the core structure of the phenethylamine 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.
A wide variety of plant and animal species produce phenethylamine. It is also produced in sufficient quantities by certain bacteria and fungi (genera Lactobacillus and Clostridium and the family Enterobacteriaceae).
Phenethylamine can be described as a primary amine. The amino group is attached to a 2-carbon or ethyl ring by attaching it to a benzene ring. It is a colourless liquid at ambient temperature and has a fishy smell. It is also soluble in water, alcohol, and ether. It has a density of 0.964g/ml, and a boiling point of 195 degrees Celsius. It reacts with carbon dioxide to create solid carbonate sodium when exposed to air. Phenethylamine, which is very basic at pKb = 4.17 or pKa= 9.83, as determined using the HCl sodium, forms a stable crystalline chloride salt with a melting temperature of 217 degrees Celsius.
Substituted Phenethylamines is a class of chemical compounds that are based on the phenethylamine structure. It consists of all derivative compounds of the phenethylamine, which can be made by substituting one or more hydrogen atoms in the core structure of the phenethylamine with substituents.
Many substituted phenethylamines are psychoactive drugs, which belong to a variety of different drug classes, including central nervous system stimulants (e.g., amphetamine), hallucinogens (e.g., 2,5-dimethoxy-4-methylamphetamine), entactogens (e.g., 3,4-methylenedioxyamphetamine), appetite suppressants (e.g. phentermine, nasal decongestants (e.g. pseudoephedrine), and antidepressants (e.g. bupropion, antiparkinson agents (e.g. selegiline) and vasopressors, e.g. ephedrine, among other things. Many psychoactive compounds have pharmacological effects by modulating the monoamine neurotransmitter system; however, there is no common mechanism of action or biological target for all members of this subclass.
Many endogenous compounds, including hormones, monoamine neurotransmitters and trace amines (e.g. dopamine and norepinephrine), can be substituted for phenethylamines. Dopamine is simply Phenethylamine with an attached hydroxyl group to the 3rd and 4th positions of the benzene rings. The class also includes many other notable recreational drugs such as MDMA (ecstasy), methamphetamine, or cathinone. All substituted amphetamines include phenethylamines.
Phenethylamines can be substituted with pharmaceutical drugs like phenelzine and phenformin.