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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%

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
Joseph M Hall et al.
Frontiers in neuroscience, 12, 773-773 (2018-11-18)
Exercise has been shown to improve or rescue cognitive functioning in both humans and rodents, and the augmented actions of neurotrophins within the hippocampus and associated regions play a significant role in the improved neural plasticity. The septohippocampal circuit is
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
Jessica J Roland et al.
Neurobiology of learning and memory, 87(1), 123-132 (2006-09-19)
A rodent model of diencephalic amnesia, pyrithiamine-induced thiamine deficiency (PTD), was used to investigate the dynamic role of hippocampal and striatal acetylcholine (ACh) efflux across acquisition of a nonmatching-to-position (NMTP) T-maze task. Changes in ACh efflux were measured in rats
Zhiwei Huang et al.
PLoS genetics, 8(11), e1003083-e1003083 (2012-12-05)
Chloroquine (CQ) and other quinoline-containing antimalarials are important drugs with many therapeutic benefits as well as adverse effects. However, the molecular targets underlying most such effects are largely unknown. By taking a novel functional genomics strategy, which employs a unique
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