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A9501

Adenosine 3′,5′-cyclic monophosphate

Name: Adenosine 3′,5′-cyclic monophosphate
Brand: SIGMA

≥98.5% (HPLC), powder

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Synonym(s):

3′,5′-Cyclic AMP, Adenosine 3′,5′-cyclophosphate, cAMP

Empirical Formula (Hill Notation):

C₁₀H₁₂N₅O₆P

CAS Number:

60-92-4

Molecular Weight:

329.21

Beilstein:

52645

EC Number:

200-492-9

MDL number:

MFCD00005845

eCl@ss:

32160414

PubChem Substance ID:

24278245

NACRES:

NA.77

Quality Level

200

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Generation of human brain region-specific organoids using a miniaturized spinning bioreactor

Qian X, et al.

Nature Protocols, 13(3), 565-565 (2018)

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)

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)

Selective expression of a dominant-negative type Iα PKA regulatory subunit in striatal medium spiny neurons impairs gene expression and leads to reduced feeding and locomotor activity.

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

GPR126 protein regulates developmental and pathological angiogenesis through modulation of VEGFR2 receptor signaling.

Hengxiang Cui et al.

The Journal of biological chemistry, 289(50), 34871-34885 (2014-09-14)

Angiogenesis, the formation of new blood vessels from pre-existing ones, is essential for development, wound healing, and tumor progression. The VEGF pathway plays irreplaceable roles during angiogenesis, but how other signals cross-talk with and modulate VEGF cascades is not clearly

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