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Tetrahydroharman information


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
CAS Number
  • 525-40-6 ☒N
  • 23844-21-5 (1S) checkY
  • 2254-36-6 (1R) checkY
  • 2506-10-7 ☒N
3D model (JSmol)
  • Interactive image
3DMet
  • B02744
ChEBI
  • CHEBI:311872 ☒N
ChemSpider
  • 82643 ☒N
  • 614612 (1S) checkY
  • 390581 (1R) checkY
EC Number
  • 219-711-4
KEGG
  • C09089 ☒N
MeSH Tetrahydroharmane
PubChem CID
  • 91522 ()
  • 704991 (1S)
  • 442025 (1R)
CompTox Dashboard (EPA)
  • DTXSID20966937 Edit this at Wikidata
InChI
  • 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
SMILES
  • CC1NCCC2=C1NC1=CC=CC=C21
Properties
Chemical formula
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).
☒N verify (what is checkY☒N ?)
Infobox references

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.

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