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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
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
Molecular Formula C13H14N2O2
Molecular Weight 230.2625
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

CNS Penetrant
2554
Curator's Comment: 1-Methyl-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) is brain penetrant in rats. No human data available.

Originator

Brossi, A. et al.
2
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/6574460

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
 0.39 µM [Ki]
Inhibitor
8297
 0.43 µM [Ki]
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of platelet aggregation and thrombosis by indole alkaloids isolated from the edible insect Protaetia brevitarsis seulensis (Kolbe).
2017 Jun
Patents

Patents

JP2008239585A
2
US4628057
2

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:52:51 GMT 2023
Edited
by admin
on Sat Dec 16 02:52:51 GMT 2023
Record UNII
QM1A4NN056
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, TRANS-(-)-
Common Name English
1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, 2,3,4,9-TETRAHYDRO-1-METHYL-, (1R-TRANS)-
Systematic Name English
2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, (1R,3S)-
Common Name English
1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, 2,3,4,9-TETRAHYDRO-1-METHYL-, (1R,3S)-
Common Name English
(1R,3S)-1-METHYLTETRAHYDRO-.BETA.-CARBOLINE-3-CARBOXYLIC ACID
Systematic Name English
1-METHYLTETRAHYDRO-.BETA.-CARBOLINE-3-CARBOXYLIC ACID, (1R,3S)-
Common Name English
Code System Code Type Description
FDA UNII
QM1A4NN056
Created by admin on Sat Dec 16 02:52:51 GMT 2023 , Edited by admin on Sat Dec 16 02:52:51 GMT 2023
PRIMARY
CAS
42438-72-2
Created by admin on Sat Dec 16 02:52:51 GMT 2023 , Edited by admin on Sat Dec 16 02:52:51 GMT 2023
PRIMARY
PUBCHEM
148447
Created by admin on Sat Dec 16 02:52:51 GMT 2023 , Edited by admin on Sat Dec 16 02:52:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID10962488
Created by admin on Sat Dec 16 02:52:51 GMT 2023 , Edited by admin on Sat Dec 16 02:52:51 GMT 2023
PRIMARY
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