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
CAS Number	525-40-6 N 23844-21-5 (1S) Y 2254-36-6 (1R) Y 2506-10-7 N
3D model (JSmol)	Interactive image
3DMet	B02674
ChEBI	CHEBI:311872 N
ChemSpider	82643 N 614612 (1S) Y 390581 (1R) Y
EC Number	219-711-4
KEGG	C09089 N
MeSH	Tetrahydroharmane
PubChem CID	91522 () 704991 (1S) 442025 (1R)
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+ Y Key: SZIDPRXJWMIIJF-MHWRWJLKSA-N Y 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 YN ?)
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.

References

• Landolt-Börnstein
• Badger, Geoffrey M.; A. F. Beecham (1951). "Isolation of Tetrahydroharman from Petalostyles labicheoides". Nature. 168 (4273): 517–518. doi:10.1038/168517b0. 
• 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

• Peganum harmala
• Harmala alkaloid