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P0256

Sigma-Aldrich

Pyrithiamine hydrobromide

~95%, crystalline

Synonym(s):

1-([4-Amino-2-methyl]-5-pyrimidylmethyl)-2-methyl-3-(β-hydroxyethyl)pyridinium bromide, Neopyrithiamine

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About This Item

Empirical Formula (Hill Notation):
C14H18N4O · 2HBr
CAS Number:
534-64-5
Molecular Weight:
420.14
EC Number:
208-604-8
MDL number:
MFCD00058193
UNSPSC Code:
12352100
PubChem Substance ID:
57654495
NACRES:
NA.22

Assay

~95%

Quality Level

200

form

crystalline

color

off-white to yellow

storage temp.

2-8°C

SMILES string

Br.[Br-].Cc1ncc(C[n+]2cccc(CCO)c2C)c(N)n1

InChI

1S/C14H19N4O.2BrH/c1-10-12(5-7-19)4-3-6-18(10)9-13-8-16-11(2)17-14(13)15;;/h3-4,6,8,19H,5,7,9H2,1-2H3,(H2,15,16,17);2*1H/q+1;;/p-1

InChI key

DMVBWVASDWGFNH-UHFFFAOYSA-M

General description

Pyrithiamine hydrobromide is a heterocyclic building block that is used as a valuable tool in organic synthesis and medicinal chemistry due to its ability to mimic thiamine deficiency and its potential for the development of new compounds with useful pharmacological properties.

Application

Pyrithiamine hydrobromide can be used as a precursor for the synthesis pyrithiamine pyrophosphate.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

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
077F0730
077F0728

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Darren Navarro et al.
Journal of neurochemistry, 106(2), 603-612 (2008-04-16)
Thiamine deficiency provides an effective model of selective neuronal cell death. (1)H and (13)C-NMR was used to investigate the effects of thiamine deficiency on the synthesis of amino acids derived from [1-(13)C]glucose in vulnerable (medial thalamus; MT) compared to non-vulnerable
Thiamine pyrophosphate riboswitches are targets for the antimicrobial compound pyrithiamine
Sudarsan, et al.
Chemistry & Biology, 12, 1325-1335 (2005)
Steven Anzalone et al.
The European journal of neuroscience, 32(5), 847-858 (2010-08-24)
Although the key neuropathology associated with diencephalic amnesia is lesions to the thalamus and/or mammillary bodies, functional deactivation of the hippocampus and associated cortical regions also appear to contribute to the memory dysfunction. For example, there is loss of forebrain
Qipeng Zhang et al.
Neurobiology of aging, 32(1), 42-53 (2009-02-24)
Thiamine pyrophosphate (TPP) and the activities of thiamine-dependent enzymes are reduced in Alzheimer's disease (AD) patients. In this study, we analyzed the relationship between thiamine deficiency (TD) and amyloid precursor protein (APP) processing in both cellular and animal models of
Identification of vitamin B1 metabolism as a tumor-specific radiosensitizing pathway using a high-throughput colony formation screen
Tiwana, et al.
Oncotarget, 6, 5978-5978 (2015)
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