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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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Stéphane Thore et al.
Science (New York, N.Y.), 312(5777), 1208-1211 (2006-05-06)
Riboswitches are untranslated regions of messenger RNA, which adopt alternate structures depending on the binding of specific metabolites. Such conformational switching regulates the expression of proteins involved in the biosynthesis of riboswitch substrates. Here, we present the 2.9 angstrom-resolution crystal
Mari Onozuka et al.
FEMS yeast research, 8(2), 266-275 (2007-11-22)
The physiological significance of thiaminase II, which catalyzes the hydrolysis of thiamin, has remained elusive for several decades. The C-terminal domains of THI20 family proteins (THI20/21/22) and the whole region of PET18 gene product of Saccharomyces cerevisiae are homologous to
Adolf Pfefferbaum et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 32(5), 1159-1177 (2006-05-26)
Wernicke's encephalopathy (WE) is characterized by lesions in thalamus, hypothalamus (including mammillary nuclei), and inferior colliculi, results in serious disabilities, has an etiology of thiamine deficiency, is treatable with thiamine, and occurs most commonly with alcoholism. Despite decades of study
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
Thiamine pyrophosphate riboswitches are targets for the antimicrobial compound pyrithiamine
Sudarsan, et al.
Chemistry & Biology, 12, 1325-1335 (2005)
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