Tetrahydroharman - Misplaced Pages

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Tetrahydroharman
Names

Preferred IUPAC name 1-Methyl-2,3,4,9-tetrahydro-1H-pyridoindole
Systematic IUPAC name 1-Methyl-1H,2H,3H,4H,9H-pyridoindole
Other names Elaeagnine Methtryptoline Tetrahydroharmane
Identifiers
CAS Number	525-40-6 23844-21-5 (1S) 2254-36-6 (1R) 2506-10-7
3D model (JSmol)	Interactive image
3DMet	B02744
ChEBI	CHEBI:311872
ChemSpider	82643 614612 (1S) 390581 (1R)
EC Number	219-711-4
KEGG	C09089
MeSH	Tetrahydroharmane
PubChem CID	91522 () 704991 (1S) 442025 (1R)
CompTox Dashboard (EPA)	DTXSID20966937
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+Key: SZIDPRXJWMIIJF-MHWRWJLKSA-N 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,6-7H2,1H3Key: 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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Tetrahydroharman(e), also known as 1-methyl-1,2,3,4-tetrahydro-β-carboline, is a general name for one of two isomers:

(1S)-1-methyl-2,3,4,9-tetrahydro-1H-pyridoindole
Calligonine ((1R)-1-methyl-2,3,4,9-tetrahydro-1H-pyridoindole)

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
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.

References

See also