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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Nagahara et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 29(4), 243-247 (1991-04-01)
The excretion and distribution of 14C were studied in rats given by oral intubation 14C-labelled (-)-(1S,3S)-1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid and its stereoisomer, (-)-(1R,3S)-1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (MTCAs), compounds that are known to become mutagenic on reaction with nitrite. For comparison, another group of rats
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
S Manabe et al.
Experimental eye research, 63(2), 179-186 (1996-08-01)
A fluorescent beta-carboline, 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3- carboxylic acid (MTCA) was identified in human normal lenses and cataractous lenses. The mean total amounts of MTCA in normal lenses (n = 7), diabetic cataractous lenses (n = 15), and senile cataractous lenses (n =
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
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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