Skip to Content
MilliporeSigma
Get 22% off for Pi Day through March 31.Save Now

A9501

Adenosine 3′,5′-cyclic monophosphate

≥98.5% (HPLC), powder, PKA activator

Synonym(s):

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

Slide 1 of 2
Sign In to View Organizational & Contract Pricing.

Select a Size

1 G

$324.00

5 G

$1,230.00

25 G

$3,040.00

$324.00

Available to ship TODAYDetails

​
Request a Bulk Order

About This Item

Empirical Formula (Hill Notation):
C10H12N5O6P
CAS Number:
60-92-4
Molecular Weight:
329.21
NACRES:
NA.77
PubChem Substance ID:
24278245
eCl@ss:
32160414
UNSPSC Code:
41106305
EC Number:
200-492-9
MDL number:
MFCD00005845
Beilstein/REAXYS Number:
52645
Assay:
≥98.5% (HPLC)
Form:
powder
Quality level:
200

Key Documents

View All Documentation

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

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

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)

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

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
  • as a component of ringer solution for perfusion studies[1]
  • to induce neuroendocrine differentiation in human lung cancer cell lines

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF7120V
BCCG7418
WXBF5025V
WXBF3184V
WXBF3434V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.
View All Related Papers

Articles

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Global Trade Item Number

SKUGTIN
A9501-1G04061833402658
A9501-25G04061832895703
A9501-5G04061832895710

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service