Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H14N2O2 |
| Molecular Weight | 230.2625 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1N[C@@H](CC2=C1NC3=CC=CC=C23)C(O)=O
InChI
InChIKey=ZUPHXNBLQCSEIA-HQJQHLMTSA-N
InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)/t7-,11+/m1/s1
(1R,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA) is a β-carboline indole alkaloid naturally occurring in plants, foods, insects, and endogenously in mammals and humans. It exerts antioxidant and antithrombotic properties. MTCA is thought to be a possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Presence of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, a precursor of a mutagenic nitroso compound, in soy sauce. | 1983 May |
|
| Endogenous formation of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3- carboxylic acid in man as the possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. | 1991 |
|
| Accumulation of 1-methyl-tetrahydro-beta-carboline-3-carboxylic acid in blood and organs of rat. A possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. | 1993 |
|
| 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid and 1,2, 3,4-tetrahydro-beta-carboline-3-carboxylic acid in fruits. | 1999 Dec |
|
| Tetrahydro-beta-carbolines, potential neuroactive alkaloids, in chocolate and cocoa. | 2000 Oct |
|
| Investigation of the tuber constituents of maca (Lepidium meyenii Walp.). | 2002 Sep 25 |
|
| Increased level of tetrahydro-beta-carboline derivatives in short-term fermented garlic. | 2006 Dec |
|
| The Methyltetrahydro-{beta}-Carbolines in Maca (Lepidium meyenii). | 2009 Sep |
|
| Inhibition of platelet aggregation and thrombosis by indole alkaloids isolated from the edible insect Protaetia brevitarsis seulensis (Kolbe). | 2017 Jun |
|
| Manipulation of the Precursor Supply in Yeast Significantly Enhances the Accumulation of Prenylated β-Carbolines. | 2017 Jun 16 |
|
| Chemical Constituents from the Flower of Hosta plantaginea with Cyclooxygenases Inhibition and Antioxidant Activities and Their Chemotaxonomic Significance. | 2017 Oct 26 |
Patents
Sample Use Guides
rats: single oral dose 1.6 mg/kg or 10 mg/kg, chronic treatment with a 10 mg/kg dose for 6 weeks.
mice: 10-50 uM (iv)
Route of Administration:
Oral
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42438-72-2
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DTXSID10962488
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