U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C13H14N2O2
Molecular Weight 230.2625
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, TRANS-

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

HIDE SMILES / InChI

Description

(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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.39 µM [Ki]
0.43 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
(1R,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid treatment resulted in a dose-dependent inhibition of TNF-a-induced secretion of PAI-1 from HUVECs, which was significant at 10-50lM