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M6517

Sigma-Aldrich

α,β-Methyleneadenosine 5′-triphosphate lithium salt

≥93% (HPLC), solid

Synonym(s):
AMP-CPP
Empirical Formula (Hill Notation):
C11H18N5O12P3 · xLi+
CAS Number:
Molecular Weight:
505.21 (free acid basis)
MDL number:
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥93% (HPLC)

form

solid

color

white

solubility

H2O: 100 mg/mL

storage temp.

−20°C

SMILES string

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

InChI

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

InChI key

NVHVREPTGDOYIC-YCSZXMBFSA-M

Gene Information

human ... P2RX1(5023)

Application

α,β-Methyleneadenosine 5′-triphosphate lithium salt has been used:
  • as P2-purinoreceptor agonist (P2X), to analyse its effects on membrane conductance in the astrocytes of caudal nucleus
  • as a P2X receptor agonist, to increase the calcium current in the neurons in satellite cells
  • to determine the functional sensitivities of purinergic agonists on P2Y receptors in rat and to determine its effect on developing outer sulcus cells

Packaging

5 mg in glass bottle
10, 25, 100 mg in poly bottle

Biochem/physiol Actions

P2 purinoceptor agonist that is more potent than ATP at the P2X subtype.

Features and Benefits

This compound is featured on the P2 Receptors: P2X Ion Channel Family and P2 Receptors: P2Y G-Protein Family pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Physical form

hygroscopic solid

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Product Information Sheet

More Documents

Quotes and Ordering

X Bo et al.
British journal of urology, 76(3), 297-302 (1995-09-01)
To characterize [3H] alpha, beta-methylene adenosine 5'-triphosphate ([3H] alpha, beta-MeATP, a radioligand for P2x-purinoceptors) binding sites in the washed homogenates and membrane preparations of human urinary bladder and, using autoradiography, to localize [3H] alpha, beta-MeATP binding sites in human bladder.
D J Trezise et al.
British journal of pharmacology, 112(1), 282-288 (1994-05-01)
1. We have previously found that the P2x-purinoceptor agonist, alpha, beta-methylene adenosine 5'-triphosphate (alpha, beta-methylene ATP), depolarizes the rat cervical vagus nerve, measured with a 'grease-gap' extracellular recording technique. This effect was attenuated by the P2 purinoceptor antagonist, suramin. In
GABA-mediated modulation of ATP-induced intracellular calcium responses in nodose ganglion neurons of the rat
Yokoyama T, et al.
Neuroscience Letters, 584, 168-172 (2015)
G Burnstock et al.
General pharmacology, 16(5), 433-440 (1985-01-01)
It is suggested that the P2-purinoceptor may be separated into two subtypes largely on the basis of the rank order of agonist potency of structural analogues of ATP and also on the activity of antagonists at the P2-purinoceptor: Subtype 1
Tanumoy Mondol et al.
Nucleic acids research, 47(4), 1977-1986 (2019-01-04)
DNA polymerase delta (Pol δ) is responsible for the elongation and maturation of Okazaki fragments in eukaryotic cells. Proliferating cell nuclear antigen (PCNA) recruits Pol δ to the DNA and serves as a processivity factor. Here, we show that PCNA

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