(R)-(+)-1-Phenylethylamine
[CAS# 3886-69-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: (R)-(+)-1-Phenylethylamine
• Synonyms: D-alpha-Phenylethylamine; R-(+)-alpha-Methylbenzylamine; D(+)-alpha-Methylbenzylamine; (+)-PEA; (R)-(+)-1-Phenylethylamine
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• CAS Registry Number: 3886-69-9
• EC Number: 223-423-4
• SMILES: C[C@H](C1=CC=CC=C1)N

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 32 °C (Expl.), 0.951 g/mL (Expl.)
• Index of Refraction: 1.533, Calc.^*,1.526 (Expl.)
• Boiling Point: 183.0±9.0 °C (760 mmHg), Calc.^*, 185.2 °C (Expl.)
• Flash Point: 79.4 °C, Calc.^*, 79 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H312-H314-H318
• Safety Statements: P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	4	H227

• Transport Information: UN 2735

Discovery and Applications

(R)-(+)-1-Phenylethylamine is an organic compound that belongs to the class of amines and is a chiral molecule with important biological and chemical properties. It is the enantiomer of 1-phenylethylamine, which is a naturally occurring compound found in various plants and animals. The (R)-(+)-enantiomer, specifically, plays a significant role in several biological processes and has applications in various chemical and pharmaceutical fields.

The compound was first synthesized in the early 20th century, with its structure and properties becoming more clearly understood through chemical analysis and synthetic advancements. It is typically obtained through enantioselective synthesis methods that yield the (R)-enantiomer, which has specific stereochemical properties distinguishing it from the (S)-enantiomer. The (R)-(+)-configuration is associated with particular pharmacological effects, which differ from those of the (S)-enantiomer and the racemic mixture of both enantiomers.

(R)-(+)-1-Phenylethylamine is widely recognized for its role in the central nervous system. It acts as a neuromodulator and is chemically related to other important biogenic amines such as dopamine, norepinephrine, and serotonin. In the human body, (R)-(+)-1-phenylethylamine functions as a trace amine and is thought to influence mood, behavior, and cognitive function. It has been studied for its potential effects on mood regulation, alertness, and attention.

The compound has garnered attention in the pharmaceutical industry due to its potential applications in drug development. It has been investigated for use in the treatment of mood disorders, such as depression and anxiety, owing to its ability to modulate neurotransmitter systems in the brain. Research suggests that (R)-(+)-1-phenylethylamine can influence the release and reuptake of monoamine neurotransmitters, particularly in the context of the central nervous system. Some studies have also explored its potential as a therapeutic agent for conditions such as attention deficit hyperactivity disorder (ADHD) and cognitive enhancement.

In addition to its pharmacological uses, (R)-(+)-1-phenylethylamine is employed in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and flavoring agents. It is used as a building block in the synthesis of other amines and derivatives that possess specific biological activities. Its ability to modify the structure and properties of other molecules makes it an important intermediate in the development of new chemical entities.

In the realm of materials science, (R)-(+)-1-phenylethylamine has also been studied for its potential role in the preparation of chiral materials, particularly in asymmetric synthesis and catalysis. The presence of the chiral center in this molecule allows it to influence the stereochemistry of reactions, making it useful in the creation of molecules with specific three-dimensional arrangements, which are important in drug discovery and molecular design.

The compound has also been investigated for its potential use in the food and fragrance industries. Due to its distinct aromatic properties, (R)-(+)-1-phenylethylamine is sometimes utilized as a flavoring agent in certain food products and in the creation of perfumes. It contributes to the fragrance profile of certain substances, where its aromatic and structural properties make it an attractive component in complex formulations.

In conclusion, (R)-(+)-1-phenylethylamine is a versatile and important chemical compound with diverse applications in pharmaceutical development, materials science, and the fragrance industry. Its biological activities, including its potential to influence mood and cognitive function, make it a subject of ongoing research, particularly in the context of neurological and psychiatric disorders. Additionally, its role as a chiral building block in synthetic chemistry and its potential for use in various industrial applications highlight its significance in both academic and commercial fields.

References

1996. Preparation of optically pure chiral amines by lipase-catalyzed enantioselective hydrolysis of N-acyl-amines. Biotechnology Techniques, 10(5).
DOI: 10.1007/bf00173249

2022. Synthesis of Antimalarial BRD5018. Synfacts, 18(07).
DOI: 10.1055/s-0041-1738389

2023. Optimization of the regioselective synthesis of mixed cellulose 3,5-dimethylphenyl and α-phenylethyl carbamate selectors as separation phases for chiral HPLC. Cellulose, 30(3).
DOI: 10.1007/s10570-022-05007-5