C9H13NO

C9H13NO is the chemical formula for a compound known as phenylethylamine. Phenylethylamine is an organic compound that acts as a central nervous system stimulant in humans. It is a naturally occurring monoamine alkaloid and trace amine derived from the amino acid phenylalanine.

Structure and Properties

Phenylethylamine has a chemical structure consisting of a benzene ring (phenyl group) attached to an ethylamine chain. Its molecular structure can be represented as:

Chemical structure of phenylethylamine

The molecular weight of phenylethylamine is 135.21 g/mol. It is a colorless liquid at room temperature and has a fishy odor. Phenylethylamine is soluble in water, ethanol, and ether.

Biological Role

Phenylethylamine is found in various organisms, including humans, where it functions as a neurotransmitter and neuromodulator. It is synthesized from the amino acid phenylalanine by the enzyme aromatic L-amino acid decarboxylase. In the human brain, phenylethylamine is believed to play a role in mood regulation and is sometimes referred to as the "love drug" due to its association with feelings of happiness and well-being.

Occurrence

Phenylethylamine is naturally present in several foods, such as chocolate, where it is thought to contribute to the mood-lifting effects of chocolate consumption. However, its concentration in food is typically too low to have significant psychoactive effects.

Pharmacology

Phenylethylamine acts by promoting the release of dopamine and norepinephrine in the brain, which are neurotransmitters associated with pleasure and alertness. It is structurally similar to amphetamines and can produce similar stimulant effects, although it is much less potent.

Related Compounds

Phenylethylamine is the parent compound of a large class of substances known as phenylethylamines, which include many psychoactive drugs, such as amphetamine, methamphetamine, and MDMA (ecstasy). These compounds share a common phenylethylamine backbone but differ in their specific chemical modifications.

Safety and Toxicity

Phenylethylamine is generally considered safe in the amounts found in food. However, in large doses, it can cause side effects such as headaches, nausea, and increased heart rate. It is metabolized in the body by the enzyme monoamine oxidase (MAO), and individuals taking MAO inhibitors should avoid phenylethylamine-containing foods to prevent adverse reactions.

See Also

• Phenylalanine
• Dopamine
• Norepinephrine
• Amphetamine
• Monoamine oxidase