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H0500

Sigma-Aldrich

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

Synonyme(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

Formule empirique (notation de Hill):
C13H14N2O2
Numéro CAS:
5470-37-1
Poids moléculaire :
230.26
Numéro MDL:
MFCD00022199
Code UNSPSC :
12352100
ID de substance PubChem :
24895402
Nomenclature NACRES :
NA.22

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

ZUPHXNBLQCSEIA-UHFFFAOYSA-N

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Catégories apparentées

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

Actions biochimiques/physiologiques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Sigma-Aldrich

339741

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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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