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| Names | |
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| Preferred IUPAC name
1-Methyl-9H-pyrido[3,4-b]indole | |
| Other names
Harman, Aribine, Aribin, Locuturine, Locuturin, Loturine, Passiflorin, 1-Methylnorharman, NSC 54439 | |
| Identifiers | |
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3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.948 
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| 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·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 their standard state (at 25 °C [77 °F], 100 kPa).
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Harmane (harman) is a heterocyclic amine 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, 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 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]
Harmane is a methylated derivativeofβ-carboline with the molecular formula C12H10N2.
| Family | Plant |
|---|---|
| Rubiaceae | Coffea arabica[1] |
| Solanaceae | Nicotiana tabacum[10] |
| Theaceae | Camellia sinensis[11] |
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.[10]
