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Phenethylamine

From Academic Kids

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
Missing image
Phenethylamine_structure.png
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, entactogens, 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.


Contents

Substituted phenethylamines

Missing image
Phenethylamine_rests.png
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

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
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 CH2CH2OH C(CH3)3 4-(2-(tert-Butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol
Amphetamine CH3 α-methyl-phenethylamine
Methamphetamine CH3 CH3 N-methyl-amphetamine
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-tert-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
DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methyl-amphetamine
DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromo-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-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

See also

External links

  • Book II of PiHKAL (http://www.erowid.org/library/books_online/pihkal/pihkal.shtml) online
  • Review and summary of PiHKAL, including table of 300+ phenethylamines: ascii (http://www.erowid.org/archive/hyperreal/drugs/psychedelics/phenethylamines/pihkal.review) postscript (http://www.erowid.org/archive/hyperreal/drugs/psychedelics/phenethylamines/pihkal.review.ps)
  • A Structural Tour of PiHKAL (http://www.erowid.org/archive/rhodium/chemistry/pihkaltour/)

Categorization

Template:Phenethylamines Template:Hallucinogenic phenethylamines

de:Phenylethylamin pl:Fenyloetyloamina

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