Phenylethylamine ( 2-phenylethylamine , phenethylamine , β-phenylethylamine , 1-amino-2-phenyl-ethane ) is a chemical compound that is the initial compound for some natural neurotransmitters , and its derivatives are psychedelics and stimulants .
| Phenylethylamine | |
|---|---|
 | |
| Are common | |
| Systematic name | Phenylethylamine (Phenethylamine), β-Phenylethylamine (2-Phenylethylamine), PEA |
| Chem. formula | C 8 H 11 N |
| Physical properties | |
| Molar mass | 121.18 g / mol |
| Density | 0.962 g / cm³ |
| Dynamic viscosity | |
| Kinematic viscosity | |
| Thermal properties | |
| T. melt. | -60 ° C |
| T. bale. | 195 ° C |
| T. aux. | |
| T. svpl. | |
| Etc. blast | |
| Steam pressure | and |
| Chemical properties | |
| pK a | |
| Optical properties | |
| Refractive index | |
| Classification | |
| Reg. CAS number | 64-04-0 |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
An oily liquid, sparingly soluble in water (4.2 ml in 100 ml of water) and good in organic solvents ( diethyl ether , ethanol , etc.).
Occurrence in nature
Phenylethylamine is produced in the organisms of many living things, from plants to mammals, including the human body [5] [6] ; it is also produced by certain fungi and bacteria (genus: Lactobacillus , Clostridium , Pseudomonas and Enterobacteriaceae ) and acts as a powerful antimicrobial agent against some pathogenic strains of E. coli (e.g. strain O157: H7 ) at sufficient concentrations.
Legal Prohibitions
Phenylethylamine at a concentration of 15 percent or more is listed as a precursor in List I (narcotic drugs, psychotropic substances and their precursors, the circulation of which in the Russian Federation is prohibited in accordance with the laws of the Russian Federation and international treaties of the Russian Federation).
Biochemical properties
Phenylethylamine is a biogenic amine that consists of a benzene ring and an aminoethyl group. It is a colorless liquid at room temperature. Phenylethylamine is soluble in water, alcohol and ether. Like other low molecular weight amines, it has a characteristic odor. In the open air, it forms a solid carbonate salt when reacted with carbon dioxide . The substance is irritating to the skin.
Biological role
- Mental stimulation
- Cheer up
- Mental concentration
Phenylethylamine, used in supplements at a dose of 400 mg, is known to be ineffective when taken orally, as it breaks down quickly.
In the brain, phenylethylamine affects mood and emotions, increases mental focus. This is due to an increase in the concentration of dopamine and norepinephrine in intersynaptic spaces. In action, it resembles amphetamine , without its inherent side effects, but psychological dependence may be developed with prolonged use ( physical dependence is possible only with parenteral administration into the cerebrospinal fluid using, for example, an implanted pump).
Scientists suggest that some types of depression are associated with a lack of endogenous phenethylamines. Interestingly, the level of phenethylamine in the brain increases by about 4 times with alcohol and smoking marijuana . .
Chemical Properties
The half-life of the substance in the blood is only 5-10 minutes, it is rapidly inactivated by the monoamine oxidase type B enzyme already in the stomach before it enters the bloodstream, which makes this component almost useless.
Drug Interactions
Some antidepressant drugs can significantly increase the concentration of β-phenylethylamine in the human central nervous system. These include a group of drugs that block the reverse neuronal uptake of monoamines and drugs that inhibit monoamine oxidase (MAO). It should be noted that IMAO type B has a greater selectivity for phenylethylamines in comparison with IMAO type A.
Some psychotropic substances of the phenylethylamine group (such as amphetamine, methamphetamine) are also able to inhibit MAO and, accordingly, increase the concentration of PEA in the body. This property is due to structural similarity with IMAO type B.
Food and Drug Content
Phenylethylamine is found in a number of foods, including chocolate , aspartame- containing sweets, and diet drinks. Even considering the high content of phenylethylamine in these products, they cannot cause euphoria due to the fact that PEA does not even have time to reach the brain.
In some cases, manufacturers intentionally add compounds that allow PEA to enter the bloodstream (such as piperine ) into products containing PEA. Such foods include many fat burning and pre-workout complexes (e.g. Craze), as well as euphoric drinks (e.g. Tushem). It should be noted that at the moment there are no research results proving the rationality of using β-phenylethylamine in these products, since the half-life of PEA in the human body is 5-10 minutes. [7]
Contrary to a widespread misconception, the drugs Phenibut and Baclofen, although considered as derivatives of γ-aminobutyric acid and β-phenylethylamine, do not contain either one or the other.
Notes
- ↑ 1 2 3 4 5 2-Phenylethylamine - Alfa Aesar .
- ↑ 1 2 3 4 5 6 Phenethylamine - Sigma-Aldrich .
- ↑ CRC Handbook of Chemistry and Physics / W. M. Haynes - 97 - Boca Raton : 2016. - P. 5–89. - ISBN 978-1-4987-5428-6
- ↑ CRC Handbook of Chemistry and Physics / W. M. Haynes - 97 - Boca Raton : 2016. - P. 3–36. - ISBN 978-1-4987-5428-6
- ↑ Berry, MD (July 2004). "Mammalian central nervous system trace amines. Pharmacologic amphetamines, physiologic neuromodulators. ” (PDF). Journal of Neurochemistry . 90 (2): 257-71. PMID 15228583 . doi: 10.1111 / j.1471-4159.2004.02501.x .
- ↑ Smith, Terence A. (1977). "Phenethylamine and related compounds in plants." Phytochemistry . 16 (1): 9-18. doi: 10.1016 / 0031-9422 (77) 83004-5 .
- ↑ Sabelli, Hector C .; JI Javaid. Phenylethylamine modulation of affect: therapeutic and diagnostic implications (February 1, 1995).
Literature
- “Handbook of a chemist” Vol. 2, L.-M.: Chemistry, 1964 p. 480–481