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M6517

Sigma-Aldrich

α,β-Methyleneadenosine 5′-triphosphate lithium salt

≥93% (HPLC), solid

Synonym(s):

AMP-CPP

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About This Item

Empirical Formula (Hill Notation):
C11H18N5O12P3 · xLi+
CAS Number:
104809-20-3
Molecular Weight:
505.21 (free acid basis)
MDL number:
MFCD00148925
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24277720
NACRES:
NA.77

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)

Related Categories

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

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Catherine A Regni et al.
The EMBO journal, 28(13), 1953-1964 (2009-06-06)
The 39-kDa Escherichia coli enzyme MccB catalyses a remarkable posttranslational modification of the MccA heptapeptide during the biosynthesis of microcin C7 (MccC7), a 'Trojan horse' antibiotic. The approximately 260-residue C-terminal region of MccB is homologous to ubiquitin-like protein (UBL) activating
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
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.
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
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