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Merck

A9501

Adenosine 3′,5′-cyclic monophosphate

≥98.5% (HPLC), powder, PKA activator

Synonym(s):

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

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1 G

1.730,00 kr.

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6.560,00 kr.

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21.320,00 kr.

1.730,00 kr.

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About This Item

Empirical Formula (Hill Notation):
C10H12N5O6P
CAS Number:
60-92-4
Molecular Weight:
329.21
Beilstein:
52645
EC Number:
200-492-9
MDL number:
MFCD00005845
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24278245
NACRES:
NA.77

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Product Name

Adenosine 3′,5′-cyclic monophosphate, ≥98.5% (HPLC), powder

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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1 of 4

This Item
A6885G6129SML1229
Adenosine 3′,5′-cyclic monophosphate ≥98.5% (HPLC), powder

Sigma-Aldrich

A9501

Adenosine 3′,5′-cyclic monophosphate

Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate ≥98.0% (HPLC), powder

Sigma-Aldrich

A6885

Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate

Guanosine 3′,5′-cyclic monophosphate sodium salt ≥99% (HPLC), powder

Sigma-Aldrich

G6129

Guanosine 3′,5′-cyclic monophosphate sodium salt

2′,3′-cGAMP sodium salt ≥98% (HPLC)

Sigma-Aldrich

SML1229

2′,3′-cGAMP sodium salt

form

powder

form

powder

form

powder

form

powder

assay

≥98.5% (HPLC)

assay

≥98.0% (HPLC)

assay

≥99% (HPLC)

assay

≥98% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

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

solubility

H2O: 10 mg/mL

solubility

H2O: 50 mg/mL

solubility

-

color

white

color

white

color

white

color

white to beige

Application

Adenosine 3′,5′-cyclic monophosphate has been used:
  • as cell culture medium supplement in embryonic spinal neurons[1][2]
  • as a component of ringer solution for perfusion studies[3]
  • to induce neuroendocrine differentiation in human lung cancer cell lines[4]

Biochem/physiol Actions

Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). The cAMP/PKA signaling pathway inhibits cell proliferation, induces differentiation and leads to apoptosis.
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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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7418
WXBF5025V
WXBF3184V
WXBF3434V
WXBF4271V

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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)
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
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)
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
View All Related Papers

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