What Is Phenylethylamine?

Phenethylamine (PEA), also known as -phenethylamine, 2-phenethylamine, is an alkaloid and monoamine neurotransmitter that increases dopamine levels in extracellular fluid and inhibits dopamine nerve activation (Neuron firing), treatment of depression. Phenethylamine has a structural isomer, namely -phenylethylamine or 1-phenylethylamine. ^[1]

Phenethylamine (PEA), also known as -phenethylamine, 2-phenethylamine, is an alkaloid and monoamine neurotransmitter that increases dopamine levels in extracellular fluid and inhibits dopamine nerve activation (Neuron firing), treatment of depression. Phenethylamine has a structural isomer, namely -phenylethylamine or 1-phenylethylamine. ^[1]

Chinese name

Phenethylamine

English name

Phenethylamine

nickname

2-phenylethylamine; 2-phenylethylamine

Chemical formula

C8H11N: C6H5CH2CH2NH2

Molecular weight

121.18

CAS Registry Number

64-04-0

EINECS registration number

200-574-4

Melting point

-60

Boiling point

194.5-195

Water soluble

Soluble in water

Density

0.964

Molar mass

121.18 g · mol¹

Boiling point

194.5-195 ° C

pKa

9.90 ± 0.10 (25 oC)

Physical and chemical properties of phenethylamine

Phenethylamine physical properties

Phenethylamine is an aromatic amine that is a colorless liquid at room temperature. Melting point -60 ° C ^[2] , boiling point 197-198 ° C, 70-71 ° C (0.93kPa), flash point 90 ° C, relative density 0.958 (24/4 ° C), refractive index 1.5290 (25 ° C). Soluble in alcohol, ether and water. Fishy smell. ^[1]

Phenethylamine Properties

Phenethylamine has strong alkalinity, can absorb carbon dioxide from the air to form corresponding carbonates, and has a fishy smell. ^[3] Phenethylamine is a strong base, which can form stable hydrochloride crystals. The melting point of this salt is 217 ° C. Phenethylamine is also a skin irritant and sensitizer. ^[1]

Structural characteristics of phenethylamine

Phenylethylamine, with molecular formula C8H11N, has a structural isomer, namely -phenylethylamine or 1-phenylethylamine. -phenylethylamine has two stereoisomer

Structural formula of phenethylamine and amphetamine

Body: (R)-(+)-1-phenethylamine and (S)-(-)-1-phenethylamine. In the human brain, ^[3] 2-phenethylamine has neuromodulating substances, neurotransmitters, and trace amines. Phenethylamine is a natural compound and can also be found in many foods, such as chocolate, especially after microbial fermentation. It is generally believed that a sufficient amount of phenethylamine from foods will have a mental effect. However, it was quickly metabolized by the enzyme monoamine gadolinium oxide, preventing it from efficiently reaching the brain. ^[4]

Uses of phenethylamine

Phenethylamine physiological effects

As early as the early 20th century, scientists discovered through human anatomy that when the mood of a person changes, a series of compounds are secreted from the base of the mesencephalon in the human brain. Such chemical molecules include phenethylamine, endorphins, and so on, which scientists call "emotional hormones." . ^[4]

Phenethylamine

Phenethylamine can be substituted by other groups on the benzene ring, side chain and amino group:

Amphetamines are homologs of phenethylamine, which are substituted by methyl (-CH3) at the alpha position of the amino group.

Catecholamines are phenylethylamines substituted at the 3,4 position of the phenyl ring by a hydroxyl group. Examples are the hormones and neurotransmitters dopamine, epinephrine and norepinephrine.

Aromatic amino acids phenylalanine and tyrosine carry a carboxyl group (-COOH) at the alpha position.

Class 2C compounds are phenethylamines substituted with methoxy at the 2,5-position of the phenyl ring, and there is no methyl substitution at the -position. ^[1]

Organic Synthesis of Phenylethylamine

This product is an intermediate of the drug hypoglycemic. Also used in other organic synthesis. ^[3]

Phenethylamine medicine

Phenethylamine is an important pharmaceutical and dye intermediate, and is mainly used in the synthesis of the following drugs in medicine ^[5]

Stimulants: (Stimulant), such as the plant alkaloids ephedrine and cathinone with the synthetic drugs Dextroamphetamine and Methylphenidate.

Hallucinogens : (Hallucinogen), such as the plant alkaloid mescaline (trimethoxyphenethylamine, meseca, Mescaline) and the synthetic drug 2C-B.

Divine stimulants: such as ecstasy.

Anorectic, such as phentermine, fenfluramine, and amphetamine.

Bronchodilators : (Bronchodilator), such as Salbutamol (Salbutamol) and Ephedrine (Ephedrine).

Antidepressant : Antidepressant, such as Venlafaxine, Bupropion, Monoamine oxidase inhibitor (MAOI), Phenelzine and Tranylcypromine. ^[5]

Note : Many of the above substituted phenethylamines can be used as drugs in pharmacology, but in real life, stimulants cannot be used in sports, and some drugs are more harmful to the body such as ecstasy, ephedra Alkali.

Ecstasy

Method for preparing phenethylamine

It is produced by the catalytic hydrogenation of phenylacetonitrile under pressure. Liquid ammonia was passed into phenylacetonitrile, mixed with Raney nickel after cooling and absorption, and then added to the autoclave to remove air and pass hydrogen. The reaction was performed at about 10 MPa at 80-120 ° C for 3 hours until no more hydrogen was absorbed, the pressure was cooled, and the solution was filtered. The filtrate was distilled under reduced pressure, and a 90-93 ° C (2kPa) fraction was collected to obtain 2-phenylethylamine. The yield was 90%. If 2-phenylethylamine hydrochloride (156-28-5) is prepared, the above filtrate is taken, adjusted to a pH of 3-4 with hydrochloric acid below 60 ° C, cooled to 5 ° C, left to stand for 8h, and filtered . The hydrochloride is flaky crystals. Melting point 223-224 ° C (217 ° C). ^[4]

Phenylethylamine safety risks

Risk term for phenethylamine

R22 Harmful if swallowed.

R34 causes burns. ^[6]

Phenylethylamine Safety Terminology

S26 After contact with eyes, rinse immediately with plenty of water and seek medical advice.

S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label if possible).

S36 / 37/39 Wear suitable protective clothing, gloves and goggles or a mask. ^[6]

Phenethylamine storage method

Long-term storage under nitrogen atmosphere.

Phenylethylamine emergency measures

Inhalation: Remove victim to fresh air and keep at rest in a place comfortable for breathing.

Ingestion: Rinse mouth. Do not induce vomiting.

Eye contact: Wash carefully with water for several minutes. Remove contact lenses if convenient and easy to operate. Continue flushing.

Skin contact: Remove / Take off all contaminated clothing immediately. Wash skin / shower with water. Wash contaminated clothing before reuse.

Call a detoxification center / doctor immediately.

Phenylethylamine fire protection measures

Suitable extinguishing agents: dry powder, foam, carbon dioxide

Unsuitable extinguishing agents: Water (Possibility of expanding disaster.)

Specific hazards: Caution, toxic fumes may be generated by decomposition at fire or high temperatures.

Specific method: Extinguish the fire from the upwind, and choose the appropriate fire extinguishing method according to the surrounding environment.

Unrelated personnel should be evacuated to a safe place.

Once in the vicinity of the fire: If safe, remove the removable container.

Special protective equipment for firefighters: Always wear personal protective equipment when fighting fires

Phenethylamine storage method

Long-term storage under nitrogen atmosphere. Store in a well-ventilated place. Keep cool. The storage must be locked.