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M1434

Sigma-Aldrich

2-Methylthioadenosine 5′-monophosphate triethylammonium salt hydrate

solid, ≥98% (HPLC)

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Synonym(s):
2-MeSAMP, 2-Methylthio-AMP triethylammonium salt hydrate
Empirical Formula (Hill Notation):
C11H16N5O7PS · xC6H15N × yH2O
CAS Number:
22140-20-1
Molecular Weight:
393.31 (anhydrous free acid basis)
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24896647
NACRES:
NA.51

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white

solubility

H2O: 20 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

O.CCN(CC)CC.CSc1nc(N)c2ncn([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)c2n1

InChI

1S/C11H16N5O7PS.C6H15N.H2O/c1-25-11-14-8(12)5-9(15-11)16(3-13-5)10-7(18)6(17)4(23-10)2-22-24(19,20)21;1-4-7(5-2)6-3;/h3-4,6-7,10,17-18H,2H2,1H3,(H2,12,14,15)(H2,19,20,21);4-6H2,1-3H3;1H2/t4-,6-,7-,10-;;/m1../s1

InChI key

YQMUWWZKFZERBT-IDIVVRGQSA-N

Related Categories

Application

2-Methylthioadenosine 5′-monophosphate triethylammonium salt hydrate has been used:

  • as a P2Y12 inhibitor to study its effects on stimulation of endocytosis in high-density lipoprotein (HDL).
  • as a P2Y12 inhibitor to study its effects on platelet recruitment in whole human blood.

Biochem/physiol Actions

2-Methylthioadenosine5′-monophosphate triethylammonium salt (2-MeSAMP) is an adenosine-based P2Y12 antagonist and ADP-dependent platelet aggregation inhibitory agent.(1) It has a potential to inhibit platelet activation throughP2Y12/G(i)-dependent mechanism.

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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Ben R Watson et al.
Metallomics : integrated biometal science, 8(1), 91-100 (2015-10-06)
Following platelet adhesion and primary activation at sites of vascular injury, secondary platelet activation is induced by soluble platelet agonists, such as ADP, ATP, thrombin and thromboxane. Zinc ions are also released from platelets and damaged cells and have been
J P Brammer et al.
British journal of pharmacology, 82(1), 61-72 (1984-05-01)
Palmitaldehyde acetal phosphatidic acid ( PGAP ) caused dose-dependent aggregation of human platelets resuspended in modified Tyrode medium, with a threshold concentration of 0.5-1 microM and an EC50 of 4 microM. Concentrations of PGAP which elicited biphasic irreversible aggregation concomitantly
Effects of P2Y1 receptor antagonism on the reactivity of platelets from patients with stable coronary artery disease using aspirin and clopidogrel.
Labarthe B, Babin J, Bryckaert M, et al.
British Journal of Pharmacology, 166(1), 221-231 (2011)
Li Dong et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 130, 110537-110537 (2020-07-28)
Rhizoma Bletillae, the tubes of Bletilla striata, has been traditionally used in China as a hemostatic agent. In preliminary studies, the major active fraction responsible for its hemostatic effect have been confirmed to be Rhizoma Bletillae polysaccharide (RBp), but the
S F Maloney et al.
Integrative biology : quantitative biosciences from nano to macro, 2(4), 183-192 (2010-05-18)
Determination of the patient-specific response to antiplatelet agents facilitates proper dosing for both acute and chronic prophylaxis. "Closed" systems (with or without flow) may fail to predict pharmacological potency in situations where platelets rapidly accumulate under flow conditions at a
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