Hygrine

Hygrine is a pyrrolidine alkaloid found in the leaves of the coca plant (Erythroxylum coca). It is a minor alkaloid in coca leaves, where it is present alongside other alkaloids such as cocaine and cinnamoylcocaine.

Structure and Properties

Hygrine is a ketone with the chemical formula C₈H₁₅NO. It consists of a pyrrolidine ring, which is a five-membered nitrogen-containing ring, attached to a propan-2-one group. The presence of the ketone group makes hygrine a relatively polar compound compared to other alkaloids found in coca leaves.

Biosynthesis

Hygrine is biosynthesized in the coca plant through the polyketide pathway. The biosynthesis involves the condensation of acetyl-CoA and malonyl-CoA units, followed by cyclization to form the pyrrolidine ring. The specific enzymes involved in the biosynthesis of hygrine are not fully characterized, but it is known to share some pathways with the biosynthesis of other pyrrolidine alkaloids.

Pharmacology

Hygrine itself is not known to have significant pharmacological effects in humans. However, it is often studied in the context of its presence in coca leaves and its potential role in the overall pharmacological profile of coca leaf extracts. Unlike cocaine, hygrine does not have stimulant properties and is not considered addictive.

Isolation and Analysis

Hygrine can be isolated from coca leaves through extraction and chromatographic techniques. Analytical methods such as gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography (HPLC) are commonly used to identify and quantify hygrine in plant extracts.

Applications

While hygrine itself does not have direct applications, its presence in coca leaves makes it of interest in the study of coca plant chemistry and the development of analytical methods for detecting coca alkaloids. It is also of interest in the study of plant alkaloid biosynthesis.

Also see

• Cocaine
• Coca plant
• Pyrrolidine
• Alkaloid
• Biosynthesis