M1380

Sigma-Aldrich

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

Synonym(s):
6MB-cAMP
Empirical Formula (Hill Notation):
C14H17N5NaO7P
CAS Number:
Molecular Weight:
421.28
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

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_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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...
Z W Yu et al.
Biochimica et biophysica acta, 1282(1), 57-62 (1996-06-13)
To further elucidate the mechanisms for short-term regulation of the receptor for insulin-like growth factor II (IGF-II), we investigated effects of insulin, cAMP and phosphatase inhibitors on cell surface 125I-IGF-II binding in rat adipocytes. Preincubation with the serine/threonine phosphatase inhibitor...
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)
F Viñals et al.
Endocrinology, 138(6), 2521-2529 (1997-06-01)
We have previously reported that innervation-dependent basal contractile activity regulates in an inverse manner the expression of GLUT1 and GLUT4 glucose transporters in skeletal muscle. Based on the facts that muscle innervation decreases and muscle denervation increases cAMP levels, we...
Y Wang et al.
Insect biochemistry and molecular biology, 26(1), 85-94 (1996-01-01)
Endocytosis of vitellogenin by isolated follicles of Hyalophora cecropia terminated after membrane-permeable analogs of cAMP or cGMP were added to the culture medium. Depending on the concentration of the analog, a lag period of 30 min to 3 h preceded...

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