Harmane


Harmane, or harman, also known as 1-methyl-β-carboline, is a heterocyclic amine and β-carboline found in a variety of foods including coffee, sauces, and cooked meat. It is also present in tobacco smoke.
Harmane is related to other alkaloids, harmine and harmaline, found in 1837 in the plant Peganum harmala. The name derives from the Arabic word for the plant, حَرْمَل.
In humans, harmane is a potent tremor-producing neurotoxin. Harmane has been found to inhibit the early stages of the growth of the malaria parasite in the gut of mosquitoes infected by the bacterium Delftia tsuruhatensis, and can be absorbed by the mosquitoes upon contact.

Pharmacology

Harmane fails to substitute for the psychedelic drug DOM in rodent drug discrimination tests. This is similar to the case of harmine but is in contrast to harmaline and 6-methoxyharmalan.

Chemistry

Harmane is a methylated derivative of β-carboline with the molecular formula C12H10N2.

Natural occurrence

In 1962, Poindexter et al. found that there was very little harmane in tobacco, but a significant amount in tobacco smoke. They showed that it is produced from tryptophan by the heat of burning the tobacco.

Society and culture

Legal status

Canada

Harmane is not a controlled substance in Canada as of 2025.