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Phenethylamine [1]
Phenethylamine structure
Phenethylamine-3d
Chemical name 2-Phenylethylamine
Other names Phenethylamine
β-Phenylethylamine
2-Phenyl-1-aminoethane
β-Aminoethylamine
2-Phenylethanamine
Chemical formula C8H11N
Molecular mass 121.18 g/mol
CAS number [64-04-0]
Density 0.964 g/cm3
Melting point -60 °C
Boiling point 194.5-195 °C
SMILES c1ccccc1CCN
NFPA 704
NFPA 704
2
2
2
 


Disclaimer and references

Phenethylamine (PEA), or β-Phenylethylamine, is an alkaloid and monoamine. In the human brain, it is believed to function as a neuromodulator or neurotransmitter (trace amine). Phenethylamine is a natural compound biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. It has been suggested that phenethylamine from food may have psychoactive effects in sufficient quantities. However, it is quickly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain.

Substituted phenethylamines are a broad and diverse class of compounds that include neurotransmitters, hormones, stimulants, hallucinogens, entactogens, anorectics, bronchodilators, and antidepressants. The phenethylamine structure can also be found as part of more complex ring systems such as the ergoline system of LSD or the morphinan system of morphine.

Chemistry Edit

Phenethylamine is an aromatic amine which is a colorless liquid at room temperature. It is soluble in water, ethanol, and ether.[1] Similar to other low molecular weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer.

Chocolate theory of loveEdit

In the early 1980s, chemistry of love researcher Michael Libowitz, author of the popular 1983 book The Chemistry of Love, remarked to reporters that “chocolate was loaded with PEA”. This became the focus for an article in The New York Times, which was then taken up by the wire services, then by magazine free-lancers, and evolved into the now eponymous “chocolate theory of love”.[2]

Substituted phenethylamines Edit

Phenethylamine rests

General structure of phenethylamines and amphetamines (see the table below).

Substituted phenethylamines carry additional chemical modifications at the phenyl ring, the sidechain, or the amino group:

Pharmacology Edit

Many substituted phenethylamines are pharmacologically active drugs due to their similarity to the monoamine neurotransmitters:

Substitution table Edit

Some of the more important phenethylamines are tabulated below. For simplicity, the stereochemistry of the sidechain is not covered in the table. Hundreds of other simple synthetic phenethylamines are known. This is due in part to the pioneering work of Alexander Shulgin, much of which is described in the book PiHKAL.

Substituted phenethylamines, tabulated by structure
Short Name Rα Rβ R2 R3 R4 R5 RN Full Name
Tyramine OH 4-hydroxy-phenethylamine
Dopamine OH OH 3,4-dihydroxy-phenethylamine
Epinephrine (Adrenaline) OH OH OH CH3 β,3,4-trihydroxy-N-methyl-phenethylamine
Norepinephrine (Noradrenaline) OH OH OH β,3,4-trihydroxyphenethylamine
Salbutamol OH OH CH2OH C(CH3)3 β,4-dihydroxy-3-hydroxymethyl-N-(t)-butyl-phenethylamine
Beta-Methyl-phenethylamine CH3 β-methyl-phenethylamine
Amphetamine CH3 α-methyl-phenethylamine
Methamphetamine CH3 CH3 N-methyl-amphetamine
Methylphenidate N,α-butylene-β-methoxycarbonyl-phenethylamine
Ephedrine,
pseudoephedrine
CH3 OH CH3 N-methyl-β-hydroxy-amphetamine
Cathine CH3 OH β-hydroxy-amphetamine
Cathinone CH3 =O β-keto-amphetamine
Methcathinone CH3 =O CH3 N-methyl-β-keto-amphetamine
Bupropion CH3 =O Cl C(CH3)3 3-chloro-N-(t)-butyl-β-keto-amphetamine
Fenfluramine CH3 CF3 CH2CH3 3-trifluoromethyl-N-ethyl-amphetamine
Phentermine CH3,CH3 α,α-dimethyl-phenethylamine
Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxy-phenethylamine
MDA CH3 -O-CH2-O- 3,4-methylenedioxy-amphetamine
MDMA CH3 -O-CH2-O- CH3 3,4-methylenedioxy-N-methyl-amphetamine
MDMC CH3 =O -O-CH2-O- CH3 3,4-methylenedioxy-N-methyl-β-keto-amphetamine
DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methyl-amphetamine
DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromo-amphetamine
DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitro-amphetamine
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromo-phenethylamine
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chloro-phenethylamine
DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodo-amphetamine
2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodo-phenethylamine
2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methyl-phenethylamine
2C-E OCH3 CH2CH3 OCH3 2,5-dimethoxy-4-ethyl-phenethylamine
2C-F OCH3 F OCH3 2,5-dimethoxy-4-Fluoro-phenethylamine
2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-Nitro-phenethylamine
2C-T-2 OCH3 SCH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine
2C-T-4 OCH3 SCHCH3CH3 OCH3 2,5-dimethoxy-4-(i)-propylthio-phenethylamine
2C-T-7 OCH3 SCH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine
2C-T-8 OCH3 SCH2CHCH2CH2 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine
2C-T-9 OCH3 S-(CH3)3C OCH3 2,5-dimethoxy-4-(t)-Butylthio-phenethylamine
2C-T-21 OCH3 SCH2CH2F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine

Graphical overview Edit

Overview Phenethylamines

See also Edit

ReferencesEdit

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