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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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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)
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.
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Articles

고리형 뉴클레오타이드를 위한 생체 활성 저분자

고리형 AMP(cAMP), 고리형 GMP(cGMP), 고리형 ADP-리보스를 포함하여 고리형 뉴클레오타이드는 GPCR 활성화에 의해 개시된 세포내 이벤트의 2차 전달자로서 광범위하게 연구되었습니다. cAMP는 주로 cAMP 의존성 단백질 인산화효소(PKA)의 활성화를 통해 모든 진핵생물 세포에서 세포 기능을 변형시키지만 cAMP 개폐 이온 채널 및 cAMP에 의해 직접 활성화되는 구아닌 뉴클레오타이드 교환 인자를 통해서도 변형시킵니다.

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.

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