Tetrahydroharman

Tetrahydroharman
Names
Preferred IUPAC name
1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
Systematic IUPAC name
1-Methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
Other names
Elaeagnine
Methtryptoline
Tetrahydroharmane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 219-711-4
KEGG
MeSH Tetrahydroharmane
  • InChI=1S/C15H13NO3/c1-19-12-8-6-11(7-9-12)10-16-14-5-3-2-4-13(14)15(17)18/h2-10H,1H3,(H,17,18)/b16-10+ checkY
    Key: SZIDPRXJWMIIJF-MHWRWJLKSA-N checkY
  • InChI=1S/C12H14N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-5,8,13-14H,6-7H2,1H3
    Key: LPIJOZBIVDCQTE-UHFFFAOYSA-N
  • CC1NCCC2=C1NC1=CC=CC=C21
Properties
C12H14N2
Molar mass 186.25296 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrahydroharman(e), also known as 1-methyl-1,2,3,4-tetrahydro-β-carboline, is a general name for one of two isomers:

  1. (1S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  2. Calligonine ((1R)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole)

Calligonine is a major alkaloid constituent of the roots of Calligonum minimum and the bark of Elaeagnus angustifolia. When taken internally, it has the effect of substantially lowering blood pressure for an extended period of time, similar to reserpine.

References

  • Landolt-Börnstein[permanent dead link‍]
  • Badger, Geoffrey M.; A. F. Beecham (1951). "Isolation of Tetrahydroharman from Petalostyles labicheoides". Nature. 168 (4273): 517–518. Bibcode:1951Natur.168..517B. doi:10.1038/168517b0. PMID 14875146. S2CID 4155160.
  • Harborne, Jeffrey B.; Herbert Baxter; Gerard Moss (1999). Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants (2 ed.). CRC Press. p. 195. ISBN 0-7484-0620-4.
  • Kar, Ashutosh (2003). Pharmacognosy and Pharmacobiotechnology. New Age Publishers. p. 580. ISBN 81-224-1501-6.

See also


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