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Merck
CN

P5865

Rp-8-PIP-cAMPS

≥98% (HPLC), solid

Synonym(s):

8-Piperidinoadenosine-3′,5′-cyclic monophosphorothioate, Rp-isomer sodium salt

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About This Item

Empirical Formula (Hill Notation):
C15H20N6O5PSNa
Molecular Weight:
450.39
UNSPSC Code:
41106305
PubChem Substance ID:
329820237
MDL number:
MFCD04037244

Key Documents

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InChI

1S/C15H21N6O5PS.Na/c16-12-9-13(18-7-17-12)21(15(19-9)20-4-2-1-3-5-20)14-10(22)11-8(25-14)6-24-27(23,28)26-11;/h7-8,10-11,14,22H,1-6H2,(H,23,28)(H2,16,17,18);/q;+1/p-1/t8-,10-,11-,14-,27-;/m1./s1

SMILES string

[Na+].Nc1ncnc2n([C@@H]3O[C@@H]4CO[P@@]([O-])(=S)O[C@H]4[C@H]3O)c(nc12)N5CCCCC5

InChI key

ILHHHOJPVCBSBI-RYTXRTGRSA-M

assay

≥98% (HPLC)

form

solid

mol wt

apparent mol wt 457.40

storage temp.

−20°C

Biochem/physiol Actions

Site-selective, lipophilic analogue of the phosphodiesterase-stable protein kinase A inhibitor Rp-cAMPS (Prod. No. A-165).

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
096K1415
116K1158
091K1156

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D Ogreid et al.
European journal of biochemistry, 221(3), 1089-1094 (1994-05-01)
8-Piperidino-cAMP has been shown to bind with high affinity to site A of the regulatory subunit of cAMP-dependent protein kinase type I (AI) whereas it is partially excluded from the homologous site (AII) of isozyme II [Ogreid, D., Ekanger, R.
Haiyan Liu et al.
Molecular pharmacology, 76(6), 1290-1301 (2009-09-08)
Bovine adrenal zona fasciculata (AZF) cells express bTREK-1 K+ channels whose inhibition by cAMP is coupled to membrane depolarization and cortisol secretion through complex signaling mechanisms. cAMP analogs with substitutions in the 6 position of the adenine ring selectively activate
Amod Godbole et al.
Nature communications, 8(1), 443-443 (2017-09-07)
A new paradigm of G-protein-coupled receptor (GPCR) signaling at intracellular sites has recently emerged, but the underlying mechanisms and functional consequences are insufficiently understood. Here, we show that upon internalization in thyroid cells, endogenous TSH receptors traffic retrogradely to the

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