Harmane
Chemical compound
From Wikipedia, the free encyclopedia
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,[1] sauces,[2] and cooked meat.[3] It is also present in tobacco smoke.[4]
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| Names | |
|---|---|
| Preferred IUPAC name
1-Methyl-9H-pyrido[3,4-b]indole | |
| Other names
Harman, 1-Methyl-β-carboline, Aribine, Aribin, Locuturine, Locuturin, Loturine, Passiflorin, 1-Methylnorharman, NSC 54439 | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.948 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H10N2 | |
| Molar mass | 182.226 g·molâ1 |
| Melting point | 235â238 °C (455â460 °F; 508â511 K) |
| Soluble to 10 mM in 1 eq. HCl
methanol: soluble 50 mg/ml | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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, ØÙرÙÙ ÙÙ (ḥarmal).
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 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).[10] It has been found to be inactive as an agonist of the serotonin 5-HT2A receptor.[11]
Harmane fails to substitute for the psychedelic drug DOM in rodent drug discrimination tests.[12] This is similar to the case of harmine but is in contrast to harmaline and 6-methoxyharmalan.[12]
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[13] |
| Theaceae | Camellia sinensis[14] |
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.[13]
Society and culture
Legal status
Canada
Harmane is not a controlled substance in Canada as of 2025.[15]