Phenethylamine

Phenethylamine
Chemical name2-Phenyl-ethylamine or
2-phenylethanamine
Chemical formulaC8H11N
Molecular mass121.18 g/mol
Density0.965 g/ml
Melting point-60 C
Boiling point200 C
CAS number64-04-0
SMILES NCCC1=CC=CC=C1
Chemical structure of Phenethylamine
Phenethylamine is an alkaloid and monoamine. In the human brain, it is discussed as a putative neuromodulator or neurotransmitter. In nature phenethylamine is synthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods, especially after microbial fermentation, e.g. in chocolate. Phenethylamine is a colorless liquid that forms a solid carbonate salt with carbon dioxide (CO2) upon exposure to air. Phenethylamine from food (e.g. chocolate) has been discussed to have psychoactive effects. However, it is quickly metabolized by the enzyme MAO-B so that significant concentrations do not reach the brain. Substituted phenethylamines are a broad and diverse class of compounds that include alkaloids, neurotransmitters, hormone, stimulants, hallucinogens, empathogens, anorectics, bronchodilators, and antidepressants. The phenethylamine structure can also be found as part of more complex ring systems like in the ergoline system of LSD or the morphinan system of morphine.

Substituted phenethylamines

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

Pharmacology

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

Substitution table

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
a href="/encyclopedia/Tyramine" title="Tyramine">Tyramine OH 4-hydroxy-phenethylamine
a href="/encyclopedia/Dopamine" title="Dopamine">Dopamine OH OH 3,4-dihydroxy-phenethylamine
a href="/encyclopedia/Epinephrine" title="Epinephrine">Epinephrine (Adrenaline) OH OH OH CH3 β,3,4-trihydroxy-N-methyl-phenethylamine
a href="/encyclopedia/Norepinephrine" title="Norepinephrine">Norepinephrine (Noradrenaline) OH OH OH β,3,4-trihydroxyphenethylamine
a href="/encyclopedia/Salbutamol" title="Salbutamol">Salbutamol OH OH CH2CH2OH C(CH3)3 4-(2-(tert-Butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol
a href="/encyclopedia/Amphetamine" title="Amphetamine">Amphetamine CH3 α-methyl-phenethylamine
a href="/encyclopedia/Methamphetamine" title="Methamphetamine">Methamphetamine CH3 CH3 N-methyl-amphetamine
a href="/encyclopedia/Ephedrine" title="Ephedrine">Ephedrine,
pseudoephedrine		 CH3 OH CH3 N-methyl-β-hydroxy-amphetamine
a href="/encyclopedia/Cathine" title="Cathine">Cathine CH3 OH β-hydroxy-amphetamine
a href="/encyclopedia/Cathinone" title="Cathinone">Cathinone CH3 =O β-keto-amphetamine
a href="/encyclopedia/Methcathinone" title="Methcathinone">Methcathinone CH3 =O CH3 N-methyl-β-keto-amphetamine
a href="/encyclopedia/Bupropion" title="Bupropion">Bupropion CH3 =O Cl C(CH3)3 3-chloro-N-tert-butyl-β-keto-amphetamine
a href="/encyclopedia/Fenfluramine" title="Fenfluramine">Fenfluramine CH3 CF3 CH2CH3 3-trifluoromethyl-N-ethyl-amphetamine
a href="/encyclopedia/Phentermine" title="Phentermine">Phentermine CH3,CH3 α,α-dimethyl-phenethylamine
a href="/encyclopedia/Mescaline" title="Mescaline">Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxy-phenethylamine
a href="/encyclopedia/3,4-methylenedioxyamphetamine" title="3,4-methylenedioxyamphetamine">MDA CH3 colspan=2| -O-CH2-O- 3,4-methylenedioxy-amphetamine
a href="/encyclopedia/MDMA" title="MDMA">MDMA CH3 colspan=2| -O-CH2-O- CH3 3,4-methylenedioxy-N-methyl-amphetamine
a href="/encyclopedia/2,5-dimethoxy-4-methylamphetamine" title="2,5-dimethoxy-4-methylamphetamine">DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methyl-amphetamine
a href="/encyclopedia/2,5-dimethoxy-4-bromoamphetamine" title="2,5-dimethoxy-4-bromoamphetamine">DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromo-amphetamine
a href="/encyclopedia/2C-B" title="2C-B">2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromo-phenethylamine
a href="/encyclopedia/2C-C" title="2C-C">2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chloro-phenethylamine
a href="/encyclopedia/2,5-dimethoxy-4-iodoamphetamine" title="2,5-dimethoxy-4-iodoamphetamine">DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodo-amphetamine
a href="/encyclopedia/2C-I" title="2C-I">2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodo-phenethylamine
a href="/encyclopedia/2C-D" title="2C-D">2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methyl-phenethylamine
a href="/encyclopedia/2C-E" title="2C-E">2C-E OCH3 CH2CH3 OCH3 2,5-dimethoxy-4-ethyl-phenethylamine
a href="/encyclopedia/2C-N" title="2C-N">2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-Nitro-phenethylamine
a href="/encyclopedia/2C-T-2" title="2C-T-2">2C-T-2 OCH3 SCH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine
a href="/encyclopedia/2C-T-4" title="2C-T-4">2C-T-4 OCH3 SCHCH3CH3 OCH3 2,5-dimethoxy-4-(i)-propylthio-phenethylamine
a href="/encyclopedia/2C-T-7" title="2C-T-7">2C-T-7 OCH3 SCH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine
a href="/encyclopedia/2C-T-8" title="2C-T-8">2C-T-8 OCH3 SCH2CHCH2CH2 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine
a href="/encyclopedia/2C-T-9" title="2C-T-9">2C-T-9 OCH3 S-(CH3)3C OCH3 2,5-dimethoxy-4-(t)-Butylthio-phenethylamine
a href="/encyclopedia/2C-T-21" title="2C-T-21">2C-T-21 OCH3 SCH2CH2F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine

See also

External links

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