Structure via PubChem · Public domain (PubChem)
tryptoline
Sign in to saveTryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of β-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.
Chemical data
- Formula
- C11H12N2
- Molecular weight
- 172.23 g/mol
- IUPAC name
- 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
- SMILES
- C1CNCC2=C1C3=CC=CC=C3N2
- InChIKey
- CFTOTSJVQRFXOF-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 27.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
250 papers- Multi-tiered chemical proteomic maps of tryptoline acrylamide-protein interactions in cancer cells.Nature chemistry · 2024
- Tryptoline Stereoprobe Elaboration Identifies Inhibitors of the GRPEL1-HSPA9 Chaperone Complex.bioRxiv : the preprint server for biology · 2025
- Tryptoline-based benzothiazoles re-sensitize MRSA to β-lactam antibiotics.Bioorganic & medicinal chemistry · 2019
- Algicidal effect of tryptoline against Microcystis aeruginosa: Excess reactive oxygen species production mediated by photosynthesis.The Science of the total environment · 2022
- Tryptoline formation by a preparation from brain with 5-methyltetrahydrofolic acid and tryptamine.Science (New York, N.Y.) · 1975
via PubMed
Wikidata facts
- Mass
- 172.1
Show 5 more facts
- chemical formula
- C₁₁H₁₂N₂
- subject has role
- neurotoxin
- canonical SMILES
- C1CNCC2=C1C3=CC=CC=C3N2
- found in taxon
- Phalaris coerulescens
- Commons category
- Tryptoline
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Pharmacology
- See also
- References
Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of β-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.
==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.
Excerpted from Wikipedia’s “tryptoline” article, available under the CC BY-SA 4.0 licence.