Tryptoline

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title: "Tryptoline" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["beta-carbolines", "n-monoalkyltryptamines", "monoamine-oxidase-inhibitors", "tryptamine-alkaloids"] topic_path: "general/beta-carbolines" source: "https://en.wikipedia.org/wiki/Tryptoline" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470618432 | ImageFile = Tryptoline.svg | ImageClass = skin-invert-image | ImageSize = | PIN = 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole | OtherNames = Noreleagnine Tetrahydronorharman 2,3,4,9-Tetrahydro-1H-β-carboline |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 96979 | 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 | InChIKey = CFTOTSJVQRFXOF-UHFFFAOYAW | ChEMBL_Ref = | ChEMBL = 269236 | StdInChI_Ref = | StdInChI = 1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 | StdInChIKey_Ref = | StdInChIKey = CFTOTSJVQRFXOF-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 16502-01-5 | UNII_Ref = | UNII = 65027TMI0H | PubChem = 107838 | SMILES = c1ccc2c(c1)c3c([nH]2)CNCC3 |Section2={{Chembox Properties | Formula = C11H12N2 | MolarMass = 172.226 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

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.

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

In-vivo formation of tryptolines has been a matter of controversy.

References

"Tryptoline".
(April 1981). "The effect of tryptolines (1, 2, 3, 4-tetrahydro-β-carbolines) on monoamine metabolism and the platelet aggregation response in human platelets". Neuroscience.

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