Harmane

Short description: Chemical compound

Harmane

Names
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

CAS Number

* 486-84-0 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:5623

ChemSpider |

* 4444755

EC Number |

* 207-642-2

KEGG |

* C09209

PubChem CID

* 5281404

UNII |

* 82D6J0535P Y

InChI

* InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3

Key: PSFDQSOCUJVVGF-UHFFFAOYSA-N

* InChI=1/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3

Key: PSFDQSOCUJVVGF-UHFFFAOYAA

SMILES

* CC1=NC=CC2=C1NC3=CC=CC=C23

Properties

Chemical formula

| C12H10N2
Molar mass | 182.226 g·mol−1
Melting point |  235–238 °C (455–460 °F; 508–511 K)

Solubility in water

| 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).

Infobox references

Tracking categories (test):

* SizeSet

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).

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.[6][7][8]

## Contents

* 1 Chemistry
* 2 Sources
* 3 See also
* 4 References

## Chemistry

Harmane is a methylated derivative of β-carboline with the molecular formula C12H10N2.

## Sources

Plant sources  Family | Plant

|

Rubiaceae | Coffea arabica[1]
Solanaceae | Nicotiana tabacum[9]
Theaceae | Camellia sinensis[10]

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.[9]

## See also

* Harmine

## References

1. ↑ 1.0 1.1 Herraiz, T; Chaparro, C (2006). "Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee". Life Sciences 78 (8): 795–802. doi:10.1016/j.lfs.2005.05.074. PMID 16139309.
2. ↑ Herraiz, T. (2004). "Relative exposure toβ-carbolines norharman and harman from foods and tobacco smoke". Food Additives and Contaminants 21 (11): 1041–50. doi:10.1080/02652030400019844. PMID 15764332.
3. ↑ Louis, E. D.; Zheng, W; Jiang, W; Bogen, K. T.; Keating, G. A. (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 70 (12): 1014–9. doi:10.1080/15287390601172015. PMID 17497412.
4. ↑ Herraiz, Tomas; Chaparro, Carolina (2005). "Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors". Biochemical and Biophysical Research Communications 326 (2): 378–86. doi:10.1016/j.bbrc.2004.11.033. PMID 15582589.
5. ↑ Claude Lotfi (1967). "Contribution à l'étude du Peganum harmala (L.) (Hermel)". http://chimie.these.free.fr/CHIMTHE 056.htm.
6. ↑ Huang, Wei; Rodrigues, Janneth; Bilgo, Etienne; Tormo, José R.; Challenger, Joseph D.; De Cozar-Gallardo, Cristina; Pérez-Victoria, Ignacio; Reyes, Fernando et al. (2023-08-04). "Delftia tsuruhatensis TC1 symbiont suppresses malaria transmission by anopheline mosquitoes" (in en). Science 381 (6657): 533–540. doi:10.1126/science.adf8141. ISSN 0036-8075. PMID 37535741. https://www.science.org/doi/10.1126/science.adf8141.
7. ↑ Offord, Catherine (3 August 2023). "Microbe stops mosquitoes from harboring malaria parasite". Science. https://www.science.org/content/article/microbe-stops-mosquitoes-harboring-malaria-parasite.
8. ↑ Naomi Grimley (Aug 4, 2023). "Chance discovery helps fight against malaria". BBC. https://www.bbc.com/news/health-66394117.
9. ↑ 9.0 9.1 Poindexter, E.H.; Carpenter, R.D. (1962). "The isolation of harmane and norharmane from tobacco and cigarette smoke". Phytochemistry 1 (3): 215–221. doi:10.1016/s0031-9422(00)82825-3. ISSN 0031-9422.
10. ↑ Jiao, Ye; Yan, Yan; He, Zhiyong; Gao, Daming; Qin, Fang; Lu, Mei; Xie, Mingyong; Chen, Jie et al. (2018-06-20). "Inhibitory effects of catechins on β-carbolines in tea leaves and chemical model systems". Food & Function 9 (6): 3126–3133. doi:10.1039/c7fo02053h. ISSN 2042-650X. PMID 29789822. https://pubmed.ncbi.nlm.nih.gov/29789822.

* v
* t
* e

Monoamine metabolism [[Biology:Enzyme modulator

Non-specific|

| AAAD|

* Substrates→Products: L-DOPA (levodopa)→Dopamine
* 5-HTP→Serotonin
* L-Histidine→Histamine
* [[Chemistry:PhenylPhenylalanine→Phenethylamine|Phenethylamine]]
* L-Tyrosine→Tyramine
* Tryptophan→Tryptamine

* Inhibitors: Benserazide
* Carbidopa
* DFMD
* Genistein
* Methyldopa

|

MAO|

* Substrates→Products (with ALDH/ALR): Epinephrine (adrenaline)→DHMA
* Metanephrine→MHPG/VMA
* Norepinephrine (noradrenaline)→DHMA
* Normetanephrine→MHPG/VMA
* Dopamine→DOPAC
* 3-Methoxytyramine→HVA
* Serotonin→5-HIAA

* Inhibitors: Non-selective: Benmoxin
* Caroxazone
* Echinopsidine
* Furazolidone
* Guineesine
* Hydralazine
* Indantadol
* Iproclozide
* Iproniazid
* Isocarboxazid
* Isoniazid
* Linezolid
* Mebanazine
* Metfendrazine
* Nialamide
* Octamoxin
* Paraxazone
* Phenelzine
* Pheniprazine
* Phenoxypropazine
* Pivhydrazine
* Procarbazine
* Safrazine
* Tranylcypromine

* Inhibitors: MAO-A-selective: Amiflamine
* Bazinaprine
* Befloxatone
* Brofaromine
* Cimoxatone
* Clorgiline
* CX157 (Tyrima)
* Eprobemide
* Esuprone
* Harmala alkaloids (e.g., harmine, harmaline, harman]], norharman, tetrahydroharmine)
* Methylene blue
* Metralindole
* Minaprine
* Moclobemide
* Pirlindole
* Sercloremine
* Tetrindole
* Toloxatone

* Inhibitors: MAO-B selective: Adarigiline
* Almoxatone
* D-Deprenyl
* Ethanol
* Ladostigil
* Lazabemide
* Milacemide
* Mofegiline
* Nicotine
* Pargyline‡
* Rasagiline
* Safinamide
* Selegiline (L-Deprenyl)
* Sembragiline

Phenethylamines
(dopamine, epinephrine]],
norepinephrine)</small>|

| PAH|

* Substrates→Products: [[Chemistry:PhenylPhenylalanine]]→Tyrosine

* Inhibitors: 3,4-Dihydroxystyrene

|

TH|

* Substrates→Products: Tyrosine→L-DOPA (levodopa)

* Inhibitors: 2-Hydroxyestradiol
* 2-Hydroxyestrone
* 3-Iodotyrosine
* Aquayamycin
* Bulbocapnine
* Metirosine
* Oudenone

DBH|

* Substrates→Products: Dopamine→Norepinephrine (Noradrenaline)

* Inhibitors: Bupicomide
* Disulfiram
* Dopastin
* Fusaric acid
* Nepicastat
* Phenopicolinic acid
* Tropolone

PNMT|

* Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline)

* Inhibitors: CGS-19281A
* SKF-64139
* SKF-7698

COMT|

* Substrates→Products: Dopamine→3-Methoxytyramine
* DOPAC→Homovanillic acid
* Norepinephrine→Normetanephrine
* Epinephrine→Metanephrine
* DOPEG→MOPEG
* DOMA→VMA
* 2-Hydroxyestradiol→2-Methoxyestradiol
* [[Chemistry:2-Hydroxy2-Hydroxyestrone]]→2-Methoxyestrone
* 4-Hydroxyestradiol→4-Methoxyestradiol
* [[Chemistry:4-Hydroxy4-Hydroxyestrone]]→4-Methoxyestrone

* Inhibitors: 2-Hydroxyestradiol
* 2-Hydroxyestrone
* Entacapone
* Neluxicapone
* Nitecapone
* Opicapone
* Tolcapone

Tryptamines
(serotonin, melatonin)|

| TPH|

* Substrates→Products: Tryptophan→5-HTP

* Inhibitors: AGN-2979
* Fenclonine (PCPA)
* Telotristat ethyl

|

AANAT|

* Substrates→Products: Serotonin→N-Acetylserotonin

ASMT|

* Substrates→Products: N-Acetylserotonin→Melatonin

Histamine|

| HDC|

* Substrates→Products: L-Histidine→Histamine

* Inhibitors: Catechin
* Alpha-Fluoromethylhistidine
* Histidine methyl ester
* Meciadanol
* Naringenin
* Tritoqualine

|

HNMT|

* Substrates→Products: Histamine→N-Methylhistamine

* Inhibitors: Amodiaquine
* Diphenhydramine
* Harmaline
* Metoprine
* Quinacrine
* SKF-91488
* Tacrine

DAO|

* Substrates→Products: Histamine→Imidazole acetic acid

* Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins

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*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AAAD]: Aromatic L-amino acid decarboxylase
*[MAO]: Monoamine oxidase
*[ALDH]: Aldehyde dehydrogenase
*[ALR]: Aldehyde reductase
*[PAH]: Phenylalanine hydroxylase
*[TH]: Tyrosine hydroxylase
*[DBH]: Dopamine beta-monooxygenase
*[PNMT]: Phenylethanolamine N-methyltransferase
*[COMT]: Catechol-O-methyl transferase
*[TPH]: Tryptophan hydroxylase
*[AANAT]: Serotonin N-acetyl transferase
*[ASMT]: Acetylserotonin O-methyltransferase
*[HDC]: Histidine decarboxylase
*[HNMT]: Histamine N-methyltransferase
*[DAO]: Diamine oxidase