1-Phenylethylamine (1-PEA or α-PEA), also known as α-methylbenzylamine, is the organic compound with the formula C₆H₅CH(NH₂)CH₃. This

primary amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

is a colorless liquid is often used in

chiral resolution Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic mixture into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term wit ...

s. Like

benzylamine Benzylamine, also known as phenylmethylamine, is an Organic chemistry, organic chemical compound with the Structural formula#Condensed formulas, condensed structural formula C6H5CH2NH2 (sometimes abbreviated as Phenyl group#Nomenclature, PhCH2NH2 ...

, it is relatively basic and forms stable ammonium salts and

imine In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...

Preparation and optical resolution

1-Phenylethylamine may be prepared by the

reductive amination Reductive amination (also known as reductive alkylation) is a form of amination that converts a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is a common method to make amine ...

acetophenone Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byproduct of the cumene ...

: : The

Leuckart reaction The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines. The reaction is an example of reductive amination. The reaction, named after Rudolf Leuckart (chemist), Rudolf Leuckart, uses either ammonium formate or ...

, using

ammonium formate Ammonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid. Reductive amination Acetone can be transformed into isopropylamine as follows: :CH3C(O)CH3 + 2 HCO2− +NH4 → (CH3)2CHNHCHO + 2 ...

, is another method for this transformation. -

malic acid Malic acid is an organic compound with the molecular formula . It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms ( ...

is used to resolve 1-Phenylethylamine, a versatile resolving agent in its own right. The dextrorotatory

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

crystallizes with the malate, leaving the levorotatory form in solution.

Pharmacology

Similarly to

and analogues like

pargyline Pargyline, sold under the brand name Eutonyl among others, is a monoamine oxidase inhibitor (MAOI) medication which has been used to treat hypertension (high blood pressure) but is no longer marketed. It has also been studied as an antidepressan ...

, 1-phenylethylamine has been found to act as a

monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...

(MAOI), as well as an

inhibitor Inhibitor or inhibition may refer to: Biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotransmi ...

of semicarbazide-sensitive amine oxidase (SSAO).

References

{{DEFAULTSORT:Phenethylamine, 1- Benzylamines Phenethylamines

Preparation and optical resolution

Pharmacology

See also

References