Myosmine

Myosmine is a pyridine alkaloid and a minor constituent of tobacco. It is chemically similar to nicotine, but has a phenyl group in place of nicotine's pyridine ring. Myosmine was first synthesized in 1899 by A. Pictet and A. Rotschy.

Chemistry

Myosmine is a heterocyclic compound with a pyrrolidine ring connected to a pyridine ring. It is a colorless, hygroscopic solid at room temperature. Myosmine is soluble in water and organic solvents, and its solutions have a strong alkaline reaction.

Biosynthesis

Myosmine is biosynthesized in tobacco plants from nicotinic acid. The biosynthesis involves the condensation of nicotinic acid with 1-methyl-Δ1-pyrrolinium cation to form myosmine.

Health effects

Myosmine is a minor tobacco alkaloid, but it has been found in the urine of smokers and non-smokers, indicating that it is a common dietary constituent. The health effects of myosmine are not well studied, but it is known to be a weak neurotoxin. It is also a potential carcinogen, as it can be converted to N-nitrosamines, which are known carcinogens.

See also

• Nicotine
• Tobacco
• Alkaloid
• Pyridine

References

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