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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 | |
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3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.948 |
| EC Number |
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| KEGG | |
| UNII | |
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| Properties | |
| C12H10N2 | |
| Molar mass | 182.226 g·mol−1 |
| Melting point | 235–238 °C (455–460 °F; 508–511 K) |
| Soluble to 10 mM in 1 eq. HCl methanol: soluble 50 mg/ml | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Harmane, orharman, also known as1-methyl-β-carboline, is aheterocyclic amine andβ-carboline found in a variety of foods includingcoffee,[1] sauces,[2] and cooked meat.[3] It is also present intobacco smoke.[4]
Harmane is related to other alkaloids,harmine andharmaline, found in 1837 in the plantPeganum harmala.[5] The name derives from the Arabic word for the plant,حَرْمَل (ḥarmal).
In humans, harmane is a potent tremor-producing neurotoxin.[6] Harmane has been found to inhibit the early stages of the growth of themalaria parasite in the gut ofmosquitoes infected by the bacteriumDelftia tsuruhatensis, and can be absorbed by the mosquitoes upon contact.[7][8][9]
Harmane fails to substitute for thepsychedelic drugDOM in rodentdrug discrimination tests.[10] This is similar to the case ofharmine but is in contrast toharmaline and6-methoxyharmalan.[10]
Harmane is amethylatedderivative ofβ-carboline with the molecular formula C12H10N2.
| Family | Plant |
|---|---|
| Rubiaceae | Coffea arabica[1] |
| Solanaceae | Nicotiana tabacum[11] |
| Theaceae | Camellia sinensis[12] |
In 1962, Poindexteret al. found that there was very little harmane in tobacco, but a significant amount in tobacco smoke. They showed that it is produced fromtryptophan by the heat of burning the tobacco.[11]
