Tryptoline

Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of beta-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.^[1]

Tryptoline

Names
Preferred IUPAC name 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole
Other names Noreleagnine Tetrahydronorharman 2,3,4,9-Tetrahydro-1H-β-carboline
Identifiers
CAS Number	16502-01-5 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL269236 Y
ChemSpider	96979 Y
ECHA InfoCard	100.156.194
PubChem CID	107838
UNII	65027TMI0H Y
CompTox Dashboard (EPA)	DTXSID10167835
InChI InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 Y Key: CFTOTSJVQRFXOF-UHFFFAOYSA-N Y InChI=1/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 Key: CFTOTSJVQRFXOF-UHFFFAOYAW
SMILES c1ccc2c(c1)c3c([nH]2)CNCC3
Properties
Chemical formula	C11H12N2
Molar mass	172.226 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

Pharmacology

Tryptolines are competitive selective inhibitors of the enzyme monoamine oxidase type A (MAO-A). 5-Hydroxytryptoline and 5-methoxytryptoline (pinoline) are the most active monoamine oxidase inhibitors (MAOIs) with IC₅₀s of 0.5 μM and 1.5 μM respectively.^[2]

Tryptolines are also potent reuptake inhibitors of serotonin and epinephrine, with a significantly greater selectivity for serotonin.^[2]

In vivo formation of tryptolines has been a matter of controversy.^[2]

See also

• Norharmane
• Harmane
• beta-Carboline
• Harmala alkaloid