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MedKoo Cat#: 563412 | Name: 2MeSAMP

Description:

WARNING: This product is for research use only, not for human or veterinary use.

2MeSAMP is a P2Y(12) antagonist. It acts by inhibiting platelet activation through P2Y(12)/G(i)-dependent mechanism.

Chemical Structure

2MeSAMP
2MeSAMP
CAS#81921-45-1

Theoretical Analysis

MedKoo Cat#: 563412

Name: 2MeSAMP

CAS#: 81921-45-1

Chemical Formula: C11H14N5Na2O7PS

Exact Mass:

Molecular Weight: 437.27

Elemental Analysis: C, 30.21; H, 3.23; N, 16.02; Na, 10.52; O, 25.61; P, 7.08; S, 7.33

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
2MeSAMP; 2-MeS-AMP bis-sodium; 2MeSAMP bis-sodium; 2 MeS AMP bis-sodium;
IUPAC/Chemical Name
2-(Methylthio)-5'-adenylic acid disodium salt
InChi Key
ADQMUQNGUFIJGD-IDIVVRGQSA-L
InChi Code
InChI=1S/C11H16N5O7PS.2Na/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;;/h3-4,6-7,10,17-18H,2H2,1H3,(H2,12,14,15)(H2,19,20,21);;/q;2*+1/p-2/t4-,6-,7-,10-;;/m1../s1
SMILES Code
O=P([O-])(OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N=C(SC)N=C32)N)O1)O)O)[O-].[Na+].[Na+]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 437.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Tourdot BE, Conaway S, Niisuke K, Edelstein LC, Bray PF, Holinstat M. Mechanism of race-dependent platelet activation through the protease-activated receptor-4 and Gq signaling axis. Arterioscler Thromb Vasc Biol. 2014 Dec;34(12):2644-50. doi: 10.1161/ATVBAHA.114.304249. Epub 2014 Oct 2. PubMed PMID: 25278289; PubMed Central PMCID: PMC4239175. 2: Li R, Diamond SL. Detection of platelet sensitivity to inhibitors of COX-1, P2Y₁, and P2Y₁₂ using a whole blood microfluidic flow assay. Thromb Res. 2014 Feb;133(2):203-10. doi: 10.1016/j.thromres.2013.10.043. Epub 2013 Nov 6. PubMed PMID: 24365044; PubMed Central PMCID: PMC3932538. 3: Liñán-Rico A, Wunderlich JE, Grants IS, Frankel WL, Xue J, Williams KC, Harzman AE, Enneking JT, Cooke HJ, Christofi FL. Purinergic autocrine regulation of mechanosensitivity and serotonin release in a human EC model: ATP-gated P2X3 channels in EC are downregulated in ulcerative colitis. Inflamm Bowel Dis. 2013 Oct;19(11):2366-79. doi: 10.1097/MIB.0b013e31829ecf4d. PubMed PMID: 23917247; PubMed Central PMCID: PMC4037929. 4: Herfindal L, Nygaard G, Kopperud R, Krakstad C, Døskeland SO, Selheim F. Off-target effect of the Epac agonist 8-pCPT-2'-O-Me-cAMP on P2Y12 receptors in blood platelets. Biochem Biophys Res Commun. 2013 Aug 9;437(4):603-8. doi: 10.1016/j.bbrc.2013.07.007. Epub 2013 Jul 12. PubMed PMID: 23850619. 5: Arachiche A, de la Fuente M, Nieman MT. Calcium mobilization and protein kinase C activation downstream of protease activated receptor 4 (PAR4) is negatively regulated by PAR3 in mouse platelets. PLoS One. 2013;8(2):e55740. doi: 10.1371/journal.pone.0055740. Epub 2013 Feb 6. Erratum in: PLoS One. 2013;8(12). doi:10.1371/annotation/0956857d-ecf5-4fb7-a834-131915a38a6a. PubMed PMID: 23405206; PubMed Central PMCID: PMC3566007. 6: Xiang B, Zhang G, Ren H, Sunkara M, Morris AJ, Gartner TK, Smyth SS, Li Z. The P2Y(12) antagonists, 2MeSAMP and cangrelor, inhibit platelet activation through P2Y(12)/G(i)-dependent mechanism. PLoS One. 2012;7(12):e51037. doi: 10.1371/journal.pone.0051037. Epub 2012 Dec 6. PubMed PMID: 23236426; PubMed Central PMCID: PMC3516503. 7: Vavra V, Bhattacharya A, Zemkova H. Facilitation of glutamate and GABA release by P2X receptor activation in supraoptic neurons from freshly isolated rat brain slices. Neuroscience. 2011 Aug 11;188:1-12. doi: 10.1016/j.neuroscience.2011.04.067. Epub 2011 May 7. PubMed PMID: 21575687. 8: McIlvain HB, Ma L, Ludwig B, Manners MT, Martone RL, Dunlop J, Kaftan EJ, Kennedy JD, Whiteside GT. Purinergic receptor-mediated morphological changes in microglia are transient and independent from inflammatory cytokine release. Eur J Pharmacol. 2010 Sep 25;643(2-3):202-10. doi: 10.1016/j.ejphar.2010.06.046. Epub 2010 Jul 13. PubMed PMID: 20621081. 9: Srinivasan S, Mir F, Huang JS, Khasawneh FT, Lam SC, Le Breton GC. The P2Y12 antagonists, 2-methylthioadenosine 5'-monophosphate triethylammonium salt and cangrelor (ARC69931MX), can inhibit human platelet aggregation through a Gi-independent increase in cAMP levels. J Biol Chem. 2009 Jun 12;284(24):16108-17. doi: 10.1074/jbc.M809780200. Epub 2009 Apr 3. PubMed PMID: 19346255; PubMed Central PMCID: PMC2713557. 10: Shenkman B, Einav Y, Salomon O, Varon D, Savion N. Testing agonist-induced platelet aggregation by the Impact-R [Cone and plate(let) analyzer (CPA)]. Platelets. 2008 Sep;19(6):440-6. doi: 10.1080/09537100802082256. Erratum in: Platelets. 2008 Dec;19(8):641. PubMed PMID: 18925512. 11: Carrasquero LM, Delicado EG, Jiménez AI, Pérez-Sen R, Miras-Portugal MT. Cerebellar astrocytes co-express several ADP receptors. Presence of functional P2Y(13)-like receptors. Purinergic Signal. 2005 Jun;1(2):153-9. doi: 10.1007/s11302-005-6211-3. Epub 2005 Mar 7. PubMed PMID: 18404500; PubMed Central PMCID: PMC2096534. 12: Seo DR, Kim SY, Kim KY, Lee HG, Moon JH, Lee JS, Lee SH, Kim SU, Lee YB. Cross talk between P2 purinergic receptors modulates extracellular ATP-mediated interleukin-10 production in rat microglial cells. Exp Mol Med. 2008 Feb 29;40(1):19-26. PubMed PMID: 18305394; PubMed Central PMCID: PMC2679320. 13: Malinin A, Pokov A, Swaim L, Kotob M, Serebruany V. Validation of a VerifyNow-P2Y12 cartridge for monitoring platelet inhibition with clopidogrel. Methods Find Exp Clin Pharmacol. 2006 Jun;28(5):315-22. PubMed PMID: 16845449. 14: Hardy AR, Hill DJ, Poole AW. Evidence that the purinergic receptor P2Y12 potentiates platelet shape change by a Rho kinase-dependent mechanism. Platelets. 2005 Nov;16(7):415-29. PubMed PMID: 16236603. 15: Takasaki J, Kamohara M, Saito T, Matsumoto M, Matsumoto S, Ohishi T, Soga T, Matsushime H, Furuichi K. Molecular cloning of the platelet P2T(AC) ADP receptor: pharmacological comparison with another ADP receptor, the P2Y(1) receptor. Mol Pharmacol. 2001 Sep;60(3):432-9. PubMed PMID: 11502873. 16: Jantzen HM, Gousset L, Bhaskar V, Vincent D, Tai A, Reynolds EE, Conley PB. Evidence for two distinct G-protein-coupled ADP receptors mediating platelet activation. Thromb Haemost. 1999 Jan;81(1):111-7. PubMed PMID: 10348701.

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