Gramine

Gramine is a naturally occurring indole alkaloid found in a variety of plants, especially those in the family Poaceae (grass family). It is structurally related to the neurotransmitter serotonin and the psychedelic drug dimethyltryptamine (DMT).

Chemistry

Gramine, also known as donaxine, is a member of the class of compounds known as indole alkaloids. It is a secondary metabolite, meaning it is not directly involved in growth, development, or reproduction of the organism, but is instead involved in ecological functions such as defense against herbivores or pathogens. Gramine has a molecular formula of C11H14N2 and a molecular weight of 174.24 g/mol.

Biosynthesis

The biosynthesis of gramine in plants begins with the amino acid tryptophan. Tryptophan is converted to tryptamine, which is then methylated by the enzyme S-adenosyl methionine (SAM) to form gramine.

Occurrence and Function

Gramine is found in a variety of plants, but is most commonly associated with the grass family, Poaceae. It has been detected in significant amounts in the reed Phragmites australis and the grass Lolium temulentum.

In plants, gramine serves as a natural defense against herbivores. It is toxic to many insects and other animals, and can deter feeding or cause death. It is also thought to have antimicrobial properties, helping to protect the plant against pathogens.

Toxicity

While gramine is toxic to many insects and other animals, it is generally considered to have low toxicity in humans. However, ingestion of large amounts can cause symptoms such as nausea, vomiting, and abdominal pain. In severe cases, it can cause seizures or loss of consciousness.

See Also

• Indole alkaloids
• Poaceae
• Serotonin
• DMT