2-PhenylethylaMine

Description

2-Phenylethylamine is a water-soluble amine with a fishy odor. It is often referred to simply as “phenethylamine”, but that can also be interpreted as 1-phenylethylamine1.
2-Phenylethylamine occurs widely in nature: in animals, plants, fungi, and bacteria alike. It has been known since at least 1890; and it was synthesized in 1909 by Treat B. Johnson and Herbert H. Guest at Yale University (New Haven, CT) via the reduction of benzyl cyanide with sodium in ethanol. Later synthetic methods included benzyl cyanide reduction with hydrogen over a Raney nickel catalyst and the reduction of β-nitrostyrene with lithium aluminum hydride.
2-Phenylethylamine is a central nervous system stimulant and is related to many psychoactive compounds such as the amphetamines and catecholamines. Noted (and controversial) chemist/psychopharmacologist Alexander Shulgin performed extensive research on 2-phenylethylamine derivatives, including 3,4-methylenedioxymethamphetamine (MDMA), best known by its street name, “ecstasy”.
Earlier this year, Narciso M. Garrido and colleagues at the University of Salamanca (Spain) published a review of 2-phenylethylamines in medicinal chemistry. Their article focused on open-chain, flexible derivatives such as the catecholamines dopamine, epinephrine (adrenaline), and norepinephrine, compared with constrained polycyclics such as morphine and berberine.
1. CAS Reg. No. 618-36-0.

Chemical properties

colourless or slightly yellow liquid with

Chemical properties

Phenethylamine has a fish odor.

Occurrence

Reported found in the oil of bitter almonds. Also found in grapes, cabbage, kale, carrots, blue and provolone cheese, fatty fish, beer, sherry, grape wines, cocoa, cauliflower, beetroot, radish, rhubarb, sake and dried bonito.

The Uses of 2-PhenylethylaMine

Phenethylamine is used in manufacturing anti-depression agents and anti diabetic drugs. It is also used as the goodds for drug jiangtangling intermediate, also used for other organic synthesis.

Definition

ChEBI: A phenylethylamine having the phenyl substituent at the 2-position.

Preparation

By reduction of benzyl cyanide with sodium metal in alcohol or with Raney-Ni.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 34, p. 3905, 1986 DOI: 10.1248/cpb.34.3905
Journal of the American Chemical Society, 94, p. 6561, 1972 DOI: 10.1021/ja00773a060
Tetrahedron Letters, 21, p. 1719, 1980 DOI: 10.1016/S0040-4039(00)77819-1

General Description

Phenethylamine, a new stimulant designer drug, was analyzed by the liquid chromatography high-resolution mass spectrometry quadrupole-time-of-flight (LC-HRMS-QTOF) method.

Safety Profile

Poison by intraperitoneal, subcutaneous, intracervical, and intravenous routes. Moderately toxic by ingestion. A strong base. A skin irritant and possible sensitizer. When heated to decomposition it emits toxic fumes of NOx. See also AMINES

Purification Methods

Distil the amine from CaH2, under reduced pressure, just before use. [Beilstein 12 H 1096, 12 IV 2453.]