2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, TRANS-(-)-

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=C2C=CC=C3)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 Target	Pharmacology	Potency
Oxidative Stress 162	Inhibitor 8,504
Thrombin 21	Inhibitor 8,504	0.39 µM [Ki]
Coagulation factor X 21	Inhibitor 8,504	0.43 µM [Ki]
Xanthine dehydrogenase 33	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pulmonary embolism 19	Primary		Preclinical	Unknown

PubMed

Show entries

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	6574460
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	1929872
Tetrahydro-beta-carbolines, potential neuroactive alkaloids, in chocolate and cocoa.	2000 Oct	11052752
Increased level of tetrahydro-beta-carboline derivatives in short-term fermented garlic.	2006 Dec	17039401
The Methyltetrahydro-{beta}-Carbolines in Maca (Lepidium meyenii).	2009 Sep	18955346

Showing 1 to 5 of 7 entries

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Patents

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

Show entries

Name

Type

Language

2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, TRANS-(-)-

Common Name

English

1-METHYLTETRAHYDRO-.BETA.-CARBOLINE-3-CARBOXYLIC ACID, (1R,3S)-

Preferred 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

Showing 1 to 5 of 6 entries

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Code System

Code

Type

Description

FDA UNII

QM1A4NN056

PRIMARY

CAS

42438-72-2

PRIMARY

PUBCHEM

148447

PRIMARY

EPA CompTox

DTXSID10962488

PRIMARY

Showing 1 to 4 of 4 entries

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SUBSTANCE RECORD


					QM1A4NN056

2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, TRANS-(-)-