A9501

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate

≥98.5% (HPLC), powder

Synonym(s):
3′,5′-Cyclic AMP, cAMP, Adenosine 3′,5′-cyclophosphate
Empirical Formula (Hill Notation):
C10H12N5O6P
CAS Number:
Molecular Weight:
329.21
Beilstein/REAXYS Number:
52645
EC Number:
MDL number:
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98.5% (HPLC)

form

powder

color

white

mp

260 °C (dec.) (lit.)

solubility

H2O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O

InChI

1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI key

IVOMOUWHDPKRLL-KQYNXXCUSA-N

Gene Information

human ... OPRK1(4986)

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Application

Adenosine 3′,5′-cyclic monophosphate has been used:
  • as cell culture medium supplement in embryonic spinal neurons
  • as a component of ringer solution for perfusion studies
  • to induce neuroendocrine differentiation in human lung cancer cell lines

Packaging

1, 5, 25 g in poly bottle

Biochem/physiol Actions

Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

Features and Benefits

This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Neuroendocrine differentiation contributes to radioresistance development and metastatic potential increase in non-small cell lung cancer
Zhu R, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1865(12), 1878-1890 (2018)
Generation of human brain region-specific organoids using a miniaturized spinning bioreactor
Qian X, et al.
Nature Protocols, 13(3), 565-565 (2018)
Tissue engineering the monosynaptic circuit of the stretch reflex arc with co-culture of embryonic motoneurons and proprioceptive sensory neurons
Guo X, et al.
Biomaterials, 33(23), 5723-5731 (2012)
Linghai Yang et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 34(14), 4896-4904 (2014-04-04)
Striatal medium spiny neurons (MSNs) mediate many of the physiological effects of dopamine, including the regulation of feeding and motor behaviors. Dopaminergic inputs from the midbrain modulate MSN excitability through pathways that involve cAMP and protein kinase A (PKA), but...
Cory M Johannessen et al.
Nature, 504(7478), 138-142 (2013-11-05)
Malignant melanomas harbouring point mutations (Val600Glu) in the serine/threonine-protein kinase BRAF (BRAF(V600E)) depend on RAF-MEK-ERK signalling for tumour cell growth. RAF and MEK inhibitors show remarkable clinical efficacy in BRAF(V600E) melanoma; however, resistance to these agents remains a formidable challenge....
Related Content
Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.
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