Harmane
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Harmane (harman) is a heterocyclic amine and β-carboline found in a variety of foods including coffee,[1] sauces,[2] and cooked meat.[3] It is also present in tobacco smoke.[4]
Harmane is related to other alkaloids, harmine and harmaline, found in 1837 in the plant Peganum harmala.[5] The name derives from the Arabic word for the plant, Script error: No such module "Lang". (Script error: No such module "Lang".).
In humans, harmane is a potent tremor-producing neurotoxin.[6] 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.[7][8][9]
Pharmacology
Harmane fails to substitute for the psychedelic drug DOM in rodent drug discrimination tests.[10] This is similar to the case of harmine but is in contrast to harmaline and 6-methoxyharmalan.[10]
Chemistry
Harmane is a methylated derivative of β-carboline with the molecular formula C12H10N2.
Natural occurrence
| Family | Plant |
|---|---|
| Rubiaceae | Coffea arabica[1] |
| Solanaceae | Nicotiana tabacum[11] |
| Theaceae | Camellia sinensis[12] |
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.[11]
See also
References
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