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M7510

Sigma-Aldrich

β,γ-Methyleneadenosine 5′-triphosphate disodium salt

≥95%, solid

Synonym(s):

AMP-PCP disodium salt, Adenylylmethylenediphosphonate disodium salt

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About This Item

Empirical Formula (Hill Notation):
C11H16N5Na2O12P3
CAS Number:
7414-56-4
Molecular Weight:
549.17
UNSPSC Code:
41106305
PubChem Substance ID:
24897166
NACRES:
NA.77

Quality Level

200

Assay

≥95%

form

solid

color

white

solubility

H2O: 10 mg/mL

storage temp.

−20°C

SMILES string

[Na+].[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)OP([O-])(=O)CP(O)([O-])=O)[C@@H](O)[C@H]3O

InChI

1S/C11H18N5O12P3.2Na/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(27-11)1-26-31(24,25)28-30(22,23)4-29(19,20)21;;/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21);;/q;2*+1/p-2/t5-,7-,8-,11-;;/m1../s1

InChI key

KZCUOVRMGTZINH-LYYWGVPGSA-L

Application

β,γ-Methyleneadenosine 5′-triphosphate disodium salt has been used as an internal standard for the UDP-hexose analysis with ion pairing high performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS).

Biochem/physiol Actions

Selective P2X purinoceptor agonist that is more potent than ATP, but less potent than α, β-methylene-L-adenosine 5′-triphosphate.

Features and Benefits

This compound is featured on the P2 Receptors: P2X Ion Channel Family page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Physical form

hygroscopic solid

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Trezise, D.J., et al.
Naunyn-Schmiedeberg'S Archives of Pharmacology, 35, 603-603 (1995)
O'Connor, S.E., et al.
British Journal of Pharmacology, 10, 640-640 (1990)
Mannose inhibits hyaluronan synthesis by down-regulation of the cellular pool of UDP-N-acetylhexosamines
Jokela TA, et al.
The Journal of Biological Chemistry, 283(12), 7666-7673 (2008)
Tony DeFalco et al.
Developmental biology, 352(1), 14-26 (2011-01-25)
During the differentiation of the mammalian embryonic testis, two compartments are defined: the testis cords and the interstitium. The testis cords give rise to the adult seminiferous tubules, whereas steroidogenic Leydig cells and other less well characterized cell types differentiate
Pil Joong Chung et al.
FEBS letters, 583(13), 2249-2254 (2009-06-10)
Histone deacetylases (HDACs) are known to function in the nucleus. Here, we report on the organellar localization of three rice HDACs, OsSIR2b, OsHDAC6, and OsHDAC10. The 35S:OsSIR2b-GFP and 35S:OsHDAC10-GFP constructs were introduced into tobacco BY2 cells. Co-localization analysis of the
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