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Merck
CN

M1380

N6-Monobutyryladenosine 3′:5′-cyclic monophosphate sodium salt

Synonym(s):

6MB-cAMP

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About This Item

Empirical Formula (Hill Notation):
C14H17N5NaO7P
CAS Number:
Molecular Weight:
421.28
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
Assay:
≥97.5% (HPLC)
Biological source:
synthetic (organic)
Form:
powder or crystals
Solubility:
water: 50 mg/mL, clear, colorless
Storage temp.:
−20°C
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biological source

synthetic (organic)

assay

≥97.5% (HPLC)

form

powder or crystals

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na].CCCC(=O)Nc1ncnc2n(cnc12)C3OC4COP(O)(=O)OC4C3O

InChI

1S/C14H18N5O7P.Na.H/c1-2-3-8(20)18-12-9-13(16-5-15-12)19(6-17-9)14-10(21)11-7(25-14)4-24-27(22,23)26-11;;/h5-7,10-11,14,21H,2-4H2,1H3,(H,22,23)(H,15,16,18,20);;

InChI key

RHNOUOJKQVKESB-UHFFFAOYSA-N

Application

N6-Monobutyryladenosine 3′:5′-cyclic monophosphate sodium salt is suitable:
  • to test the hypothesis that it stimulates the long-lasting potentiation of post ganglionic response
  • as protein kinase A activator, in human primary cultured thyrocytes for analyzing the modulations in cAMP cascade regulated gene expression
  • to analyse its effect on progesterone production in corpus luteum isolated from pseudopregnant rabbits

Biochem/physiol Actions

Membrane permeable analog of cAMP that activates protein kinase A and is resistant to degradation by phosphodiesterase

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Ketty Bacallao et al.
PloS one, 8(12), e82354-e82354 (2013-12-19)
In Schwann cells (SCs), cyclic adenosine monophosphate (cAMP) not only induces differentiation into a myelinating SC-related phenotype, but also synergistically enhances the mitogenic action of growth factors such as neuregulin. To better understand the molecular mechanism by which cAMP exerts
Estrogen Uncouples Steroidogenesis from 3?, 5?-Cyclic Adenosine Monophosphate Regulation in the Rabbit Corpus Luteum
Townson DH, et al.
Biology of Reproduction, 53(3), 718-723 (1995)
T Nesbitt et al.
Endocrinology, 124(3), 1184-1189 (1989-03-01)
Previously we have established that abnormal regulation of renal 25-hydroxyvitamin D (25OHD)-1 alpha-hydroxylase in Hyp mice involves the PTH-adenylate cyclase component of enzyme activation. However, it remains unknown if the muted effects of PTH result from 1) abnormal second messenger
Long-term regulation of synaptic acetylcholine release and nicotinic transmission: the role of cyclic AMP
Briggs CA, et al.
British Journal of Pharmacology, 93(2), 399-411 (1988)
T T Puck et al.
Somatic cell and molecular genetics, 17(5), 489-503 (1991-09-01)
Genome exposure studies were carried out on malignant CHO-K1 and C6 rat glioma cells and their respective, phenotypically normal counterparts (reverse-transformed CHO-K1, and both reverse-transformed C6 glioma and normal rat fibroblasts). Cells were subjected to the nick-translation technique previously developed

Global Trade Item Number

SKUGTIN
M1380-100MG04061833007624
M1380-25MG04061833007631

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