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Safety Information

H0500

Sigma-Aldrich

1,2,3,4-Tetrahydroharmane-3-carboxylic acid

Synonym(s):

1-Methyl-1,2,3,4-Tetrahydropyrido[3,4-b]indole-3-carboxylic acid, 1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, NSC 26225

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About This Item

Empirical Formula (Hill Notation):
C13H14N2O2
CAS Number:
5470-37-1
Molecular Weight:
230.26
MDL number:
MFCD00022199
UNSPSC Code:
12352100
PubChem Substance ID:
24895402
NACRES:
NA.22

storage temp.

−20°C

Quality Level

100

SMILES string

CC1NC(Cc2c1[nH]c3ccccc23)C(O)=O

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)

InChI key

ZUPHXNBLQCSEIA-UHFFFAOYSA-N

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Application

Reactant involved in synthesis of molecules for biological studies including:
  • Cytotoxicity and insecticidal activities of harmine derivatives
  • Isoquinolines, β-carbolines, and 3-deazapurines via oxidative decarboxylation
  • Cytotoxic evaluation of 1,3-di- and 1,3,9-trisubstituted β-carbolines

Biochem/physiol Actions

Implicated in eosinophilia-myalgia syndrome associated with L-tryptophan ingestion.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR6684V
080K1731
102H0626
026H0642

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H Tsuchiya et al.
Journal of pharmaceutical sciences, 83(3), 415-418 (1994-03-01)
A high-performance liquid chromatographic method was developed to quantify 1,2,3,4-tetrahydro-beta-carboline (TBC) and 1-methyl-1,2,3,4-tetrahydro-beta-carboline (MTBC) in human urine. Urine samples with added internal standard were subjected to a reaction with fluorescamine and solvent extractions to remove the precursor tryptamine, which readily
J Adachi et al.
Archives of toxicology, 65(6), 505-509 (1991-01-01)
1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) is now thought to be a possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. In the present study a factor affecting endogenous formation of MTCA in 32 healthy men is studied. Urinary excretions of
B Gutsche et al.
Journal of chromatography. A, 767(1-2), 101-106 (1997-04-11)
A rapid and sensitive method is described for the detection of 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, 1-methyl-1,2,3,4- tetrahydro-beta-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-beta-carboline by electrospray ionization tandem mass spectrometry coupled to liquid chromatography. In combination with selected reaction monitoring (SRM) detection limits of 3 ng
V Bantseev et al.
Biochemistry and molecular biology international, 42(6), 1189-1197 (1997-09-26)
The effect of several antioxidants and cysteine-elevating precursor drugs (prodrugs) was tested on lens damage occurring after in vitro exposure to low levels of 60Co-gamma-irradiation, to simulate in vitro the exposure to radiation in vivo of (1) astronauts (2) jet
Y Yamaguchi et al.
Biochemical and biophysical research communications, 178(3), 1008-1013 (1991-08-15)
While the pathogenesis of eosinophilia-myalgia syndrome (EMS) remains obscure, the ingestion of L-trypophan (LT) and possibly certain constituents in the LT product might be associated. We investigated the effect of chemically synthesized substances, 1,1'-ethylidene bis[tryptophan] (EBT) and its decomposition product
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