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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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100 MG
RM 435.00

RM 435.00

Estimated to ship on14 May 2025

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100 MG
RM 435.00

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

RM 435.00

Estimated to ship on14 May 2025

Request a Bulk Order

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR6684V
080K1731
102H0626
026H0642

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Y Ogawa et al.
Archives of toxicology, 67(4), 290-293 (1993-01-01)
1-Methyl-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) may cause eosinophilia-myalgia syndrome (EMS) associated with ingestion of L-tryptophan. The distribution and excretion of MTCA were studied in rats which had received perorally a single 1.6 mg/kg dose of MTCA. MTCA concentrations in blood, kidney, liver
J G Zangrilli et al.
Biochemistry and molecular biology international, 37(5), 925-933 (1995-11-01)
Eosinophilia-myalgia syndrome (EMS), a recently described inflammatory disorder characterized by myalgia, peripheral eosinophilia, and multisystem inflammation is associated with L-tryptophan consumption. Fibrosis of various tissues due to excessive accumulation of type I collagen is a prominent late manifestation of the
From the Centers for Disease Control. Analysis of L-tryptophan for the etiology of eosinophilia-myalgia syndrome.
JAMA, 264(13), 1656-1656 (1990-10-03)
D E Brenneman et al.
The Journal of pharmacology and experimental therapeutics, 266(2), 1029-1035 (1993-08-01)
The L-tryptophan eosinophilia myalgia syndrome (L-TRP-EMS), an inflammatory syndrome characterized by eosinophilia, myalgias, perimyositis, fasciitis and neuropathies, occurred in epidemic proportions in the United States in the summer and fall of 1989. The neuropathic clinical features in L-TRP EMS are
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 =
View All Related Papers

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