Tetrahydroharman

Tetrahydroharman, or tetrahydroharmane, also known as 1-methyl-1,2,3,4-tetrahydro-β-carboline, is a β-carboline and 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)

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
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)
CompTox Dashboard (EPA)	DTXSID901027440
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

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.

See also

• Substituted β-carboline
• Peganum harmala
• Harmala alkaloid

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.