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Harmane

Chemical compound

methanol: soluble 50 mg/ml}}

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.

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

Family	Plant
Rubiaceae	Coffea arabica
Solanaceae	last1=Poindexter	first1=E.H.	last2=Carpenter	first2=R.D.	title=The isolation of harmane and norharmane from tobacco and cigarette smoke	journal=Phytochemistry	volume=1	issue=3	year=1962	issn=0031-9422	doi=10.1016/s0031-9422(00)82825-3	pages=215–221	bibcode=1962PChem...1..215P }}
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.

Society and culture

Legal status

Canada

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

References

(2006). "Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee". Life Sciences.
(2004). "Relative exposure toβ-carbolines norharman and harman from foods and tobacco smoke". Food Additives and Contaminants.
(2007). "Quantification of the neurotoxic beta-carboline harmane in barbecued/grilled meat samples and correlation with level of doneness". Journal of Toxicology and Environmental Health, Part A.
(2005). "Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors". Biochemical and Biophysical Research Communications.
(1967). "Contribution à l'étude du Peganum harmala (L.) (Hermel)".
(2008). "Elevated blood harmane (1-methyl-9H-pyrido[3,4-b]indole) concentrations in essential tremor". Neurotoxicology.
(2023-08-04). "Delftia tsuruhatensis TC1 symbiont suppresses malaria transmission by anopheline mosquitoes". Science.
Offord, Catherine. (3 August 2023). "Microbe stops mosquitoes from harboring malaria parasite". [[Science (journal).
(Aug 4, 2023). "Chance discovery helps fight against malaria". BBC.
(January 1983). "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines". Eur J Pharmacol.
(1962). "The isolation of harmane and norharmane from tobacco and cigarette smoke". Phytochemistry.
(2018-06-20). "Inhibitory effects of catechins on β-carbolines in tea leaves and chemical model systems". Food & Function.
"Controlled Drugs and Substances Act".

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

beta-carbolines malaria monoamine-oxidase-inhibitors

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