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Merck

16609

1,2-Bis(2-amino-5-methylphenoxy)ethane-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl) ester

≥95% (HPLC)

Synonym(s):

5,5′-Dimethyl-BAPTA-AM, MAPTAM

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About This Item

Empirical Formula (Hill Notation):
C36H44N2O18
CAS Number:
147504-94-7
Molecular Weight:
792.74
UNSPSC Code:
12352108
NACRES:
NA.32
PubChem Substance ID:
57647583
MDL number:
MFCD00036856
Beilstein/REAXYS Number:
8181451

Product Name

1,2-Bis(2-amino-5-methylphenoxy)ethane-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl) ester, ≥95% (HPLC)

InChI

1S/C36H44N2O18/c1-23-7-9-29(37(15-33(43)53-19-49-25(3)39)16-34(44)54-20-50-26(4)40)31(13-23)47-11-12-48-32-14-24(2)8-10-30(32)38(17-35(45)55-21-51-27(5)41)18-36(46)56-22-52-28(6)42/h7-10,13-14H,11-12,15-22H2,1-6H3

SMILES string

CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)c1ccc(C)cc1OCCOc2cc(C)ccc2N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O

InChI key

HEOJVQZWOLQUDR-UHFFFAOYSA-N

assay

≥95% (HPLC)

solubility

DMSO: soluble

storage temp.

−20°C

Quality Level

100

Other Notes

Membrane-permeable improved derivative of BAPTA; chelators for intracellular calcium incorporated non-disruptively into cells

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP1026
BCCJ8749
BCCF0843
BCBT7170
BCBS2037V

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J M Dubinsky
Neuroscience letters, 150(2), 129-132 (1993-02-19)
In an attempt to probe the relationship between excitotoxicity and increases in intracellular calcium ([Ca2+]i), BAPTA-AM and its analogs were applied to cultured hippocampal neurons. Chelation of [Ca2+]i depressed and prolonged transient responses to glutamate and did not effect elevation
Sebastian John et al.
Frontiers in molecular neuroscience, 10, 171-171 (2017-07-01)
Glioblastoma multiforme (GBM) is a highly aggressive type of brain tumor with an extremely poor prognosis. Recent evidences have shown that the "biomechanical imbalances" induced in GBM patient-derived glioblastoma cells (GC) and in vivo via the administration of synthetic small
T Tiffert et al.
The Journal of physiology, 505 ( Pt 2), 403-410 (1998-01-10)
1. A recently developed method of measuring cytoplasmic Ca2+ buffering in intact red cells was applied to re-evaluate the intracellular Ca2+ binding properties of the Ca2+ chelators benz2 and BAPTA. Incorporation of the free chelators was accomplished by incubating the
Nida Arif et al.
The EMBO journal, 40(9), e106113-e106113 (2021-02-20)
Leukocyte extravasation is an essential step during the immune response and requires the destabilization of endothelial junctions. We have shown previously that this process depends in vivo on the dephosphorylation of VE-cadherin-Y731. Here, we reveal the underlying mechanism. Leukocyte-induced stimulation
Shah Alam et al.
Cells, 9(10) (2020-10-02)
We have shown that sphingosine 1-phosphate (S1P) generated by sphingosine kinase 2 (SK2) is toxic in neurons lacking S1P-lyase (SGPL1), the enzyme that catalyzes its irreversible cleavage. Interestingly, patients harboring mutations in the gene encoding this enzyme (SGPL1) often present
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