Harmane

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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:5623
ChemSpider
  • 4444755
ECHA InfoCard 100.006.948 Edit this at Wikidata
EC Number
  • 207-642-2
KEGG
  • C09209
PubChem CID
  • 5281404
UNII
  • 82D6J0535P checkY
CompTox Dashboard (EPA)
  • DTXSID80197568 Edit this at Wikidata
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
  • 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
Chemical compound

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]

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[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]

See also

References

  1. ^ a b 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. S2CID 216644379.
  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. Bibcode:2007JTEHA..70.1014L. doi:10.1080/15287390601172015. PMC 4993204. 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)".
  6. ^ Louis, Elan D; Jiang, Wendy; Pellegrino, Kathryn M; Rios, Eileen; Factor-Litvak, Pam; Henchcliffe, Claire; Zheng, Wei (2008). "Elevated blood harmane (1-methyl-9H-pyrido[3,4-b]indole) concentrations in essential tremor". Neurotoxicology. 29 (2): 294–300. doi:10.1016/j.neuro.2007.12.001. PMC 2291546. PMID 18242711.
  7. ^ Huang, Wei; Rodrigues, Janneth; Bilgo, Etienne; Tormo, José R.; Challenger, Joseph D.; De Cozar-Gallardo, Cristina; Pérez-Victoria, Ignacio; Reyes, Fernando; Castañeda-Casado, Pablo; Gnambani, Edounou Jacques; Hien, Domonbabele François de Sales; Konkobo, Maurice; Urones, Beatriz; Coppens, Isabelle; Mendoza-Losana, Alfonso (2023-08-04). "Delftia tsuruhatensis TC1 symbiont suppresses malaria transmission by anopheline mosquitoes". Science. 381 (6657): 533–540. Bibcode:2023Sci...381..533H. doi:10.1126/science.adf8141. hdl:10044/1/105278. ISSN 0036-8075. PMID 37535741. S2CID 260440907.
  8. ^ Offord, Catherine (3 August 2023). "Microbe stops mosquitoes from harboring malaria parasite". Science.
  9. ^ Naomi Grimley (Aug 4, 2023). "Chance discovery helps fight against malaria". BBC.
  10. ^ a b Poindexter, E.H.; Carpenter, R.D. (1962). "The isolation of harmane and norharmane from tobacco and cigarette smoke". Phytochemistry. 1 (3): 215–221. Bibcode:1962PChem...1..215P. doi:10.1016/s0031-9422(00)82825-3. ISSN 0031-9422.
  11. ^ Jiao, Ye; Yan, Yan; He, Zhiyong; Gao, Daming; Qin, Fang; Lu, Mei; Xie, Mingyong; Chen, Jie; Zeng, Maomao (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.
  • v
  • t
  • e
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine, epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-monooxygenase
PNMTTooltip Phenylethanolamine N-methyltransferase
  • Inhibitors: CGS-19281A
  • SKF-64139
  • SKF-7698
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin, melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
  • Substrates→Products: L-Histidine→Histamine
HNMTTooltip Histamine N-methyltransferase
  • Substrates→Products: Histamine→N-Methylhistamine
DAOTooltip Diamine oxidase
  • Substrates→Products: Histamine→Imidazole acetic acid
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins