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Key Documents

SML1941

Sigma-Aldrich

CGP3466B maleate salt

≥98% (HPLC)

Synonym(s):

CGP 3466B, Dibenz[b,f]oxepin-10-methanamine, N-methyl-N-2-propyn-1-yl-, (2Z)-2-butenedioate (1:1), N-(Dibenz[b,f]oxepin-10-ylmethyl)-N-methyl-N-(2-propynyl)amine monomaleic acid salt, Omigapil maleate salt, TCH346

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About This Item

Empirical Formula (Hill Notation):
C19H17NO · C4H4O4
CAS Number:
200189-97-5
Molecular Weight:
391.42
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

N(CC1=Cc2c(cccc2)Oc3c1cccc3)(CC#C)C.OC(=O)\C=C/C(=O)O

InChI

1S/C19H17NO.C4H4O4/c1-3-12-20(2)14-16-13-15-8-4-6-10-18(15)21-19-11-7-5-9-17(16)19;5-3(6)1-2-4(7)8/h1,4-11,13H,12,14H2,2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

SQAZQLMBEHYFJA-BTJKTKAUSA-N

Biochem/physiol Actions

CGP3466B, also known as Omigapil maleate and TCH346, is a potent inhibitor of glyceraldehyde-3-phosphate dehydrogenase (GAPDH). It has been shown to have neuroprotective activity and received U.S. FDA Fast Track Designation for the treatment of congenital muscular dystrophy in May 2016.
Inhibitor of glyceraldehyde-3-phosphate dehydrogenase (GAPDH), neuroprotective.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000191296
0000191297
0000191297
0000191296
0000127533

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Prasun Guha et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(5), 1417-1422 (2016-01-21)
Cocaine exerts its behavioral stimulant effects by facilitating synaptic actions of neurotransmitters such as dopamine and serotonin. It is also neurotoxic and broadly cytotoxic, leading to overdose deaths. We demonstrate that the cytotoxic actions of cocaine reflect selective enhancement of
Natasha T Snider et al.
PloS one, 11(8), e0160982-e0160982 (2016-08-12)
The glycolytic enzyme glyceraldehyde-3-phosphate dehydrogenase (GAPDH) signals during cellular stress via several post-translational modifications that change its folding properties, protein-protein interactions and sub-cellular localization. We examined GAPDH properties in acute mouse liver injury due to ethanol and/or acetaminophen (APAP) treatment.
Qing Yu et al.
PloS one, 8(6), e65468-e65468 (2013-06-14)
Congenital muscular dystrophy is a distinct group of diseases presenting with weakness in infancy or childhood and no current therapy. One form, MDC1A, is the result of laminin alpha-2 deficiency and results in significant weakness, respiratory insufficiency and early death.

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