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
PubChemCID	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 theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Tryptoline, also known astetrahydro-β-carboline andtetrahydronorharmane, is a naturalorganic derivative ofβ-carboline. It is analkaloid chemically related totryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively astryptolines.^[1]

Tryptolines are competitive selective inhibitors of theenzymemonoamine oxidase type A (MAO-A).5-Hydroxytryptoline and5-methoxytryptoline (pinoline) are the most activemonoamine oxidase inhibitors (MAOIs) withIC₅₀s of 0.5 μM and 1.5 μM respectively.^[2]

Tryptolines are also potentreuptake inhibitors ofserotonin andepinephrine, with a significantly greater selectivity for serotonin.^[2]

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

• Substituted β-carboline
• Norharmane
• Harmane
• β-Carboline
• Harmala alkaloid

• Beta-Carbolines
• N-Monoalkyltryptamines
• Monoamine oxidase inhibitors
• Tryptamine alkaloids

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