Harmane
Chemical compound
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 (ḥarmal).
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.
01Pharmacology
Pharmacodynamics
Harmane is a potent reversible inhibitor of monoamine oxidase A (RIMA), with an IC50Tooltip half-maximal inhibitory concentration of 60 nM. It is also a weak dopamine reuptake inhibitor (DRI), with an IC50 of 1,490 nM at the dopamine transporter (DAT).
Harmane shows weak affinity for the serotonin 5-HT2B and 5-HT2C receptors (Ki = 267 nM and 1,135 nM, respectively), but not for the serotonin 5-HT2A receptor (Ki = >10,000 nM). It has been found to be inactive as an agonist of the serotonin 5-HT2A receptor.
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.
02Chemistry
Harmane is a methylated derivative of β-carboline with the molecular formula C12H10N2.
03Natural occurrence
| Family | Plant |
|---|---|
| Rubiaceae | Coffea arabica |
| Solanaceae | Nicotiana tabacum |
| Theaceae | Camellia sinensis |
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.
04Society and culture
Sources and credits
This article is adapted from the Wikipedia article “Harmane”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Harmane.svg by Eloil, Public domain
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