Harmane

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Harmane
Harmane.svg
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.948 Edit this at Wikidata
EC Number
  • 207-642-2
KEGG
UNII
  • 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
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[1]

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

Harmane (harman) is a heterocyclic amine found in a variety of foods including coffee,[2] sauces,[3] and cooked meat.[4] It is also present in tobacco smoke.[5]

Chemistry[edit]

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

Sources[edit]

Plant sources
Family Plant
Rubiaceae Coffea arabica[2]
Solanaceae Nicotiana tabacum[6]
Theaceae Camellia sinensis[7]

See also[edit]

References[edit]

  1. ^ "Harmane". tocris.com.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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. PMC 4993204. PMID 17497412.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.