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3'-Adenylic acid

Cat No.:V5959 Purity: ≥98%
Adenosine 3′-monophosphate (3′-AMP) is a nucleotide that is an agonist of cyclic AMP production.
3'-Adenylic acid
3'-Adenylic acid Chemical Structure CAS No.: 84-21-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Adenosine 3′-monophosphate (3′-AMP) is a nucleotide that is an agonist of cyclic AMP production.
3'-Adenylic acid (CAS# 84-21-9), also known as adenosine 3'-monophosphate (3'-AMP), is a nucleotide consisting of adenine, ribose, and a phosphate group attached at the 3' position. It has the molecular formula C₁₀H₁₄N₅O₇P and molecular weight 347.22 g/mol. 3'-Adenylic acid is a key component of RNA and is involved in various biological processes including cellular metabolism, signal transduction, and energy transfer. It is an endogenous metabolite and is used in research to study nucleotide metabolism and signaling pathways. The compound is not a therapeutic agent but is used as a research tool and as a dietary supplement ingredient in some contexts.
Biological Activity I Assay Protocols (From Reference)
Targets
3'-Adenylic acid does not have a specific pharmacological target as a therapeutic agent. As an endogenous nucleotide, it is involved in multiple cellular processes including RNA synthesis, energy metabolism, and nucleotide signaling. It can be metabolized to adenosine, which acts on adenosine receptors (A1, A2A, A2B, A3) and plays roles in cardiovascular, neurological, and immune function. However, 3'-AMP itself is not a selective agonist or antagonist of these receptors. It may also act as a substrate for enzymes involved in nucleotide metabolism, including nucleotidases and kinases.
ln Vitro
In vitro, 3'-adenylic acid is used as a substrate and standard in biochemical assays. It can be hydrolyzed by 3'-nucleotidase to produce adenosine and phosphate. It can be phosphorylated by kinases to form adenosine diphosphate (ADP) and adenosine triphosphate (ATP). It serves as a building block for RNA synthesis in vitro. It may have effects on cellular signaling pathways through its metabolism to adenosine, which can activate adenosine receptors. It has been studied for its potential neuroprotective and cardioprotective effects, although these are likely mediated through its metabolites rather than the parent compound.
ln Vivo
In vivo, 3'-adenylic acid is an endogenous metabolite present in all cells. It is involved in nucleotide metabolism and energy homeostasis. As a dietary supplement, it has been marketed for various health benefits including cardiovascular support, athletic performance, and neuroprotection, although the evidence for these benefits is limited. Its effects are likely mediated through its metabolism to adenosine and other nucleotides rather than through direct activity. It is not used as a therapeutic agent for specific diseases. Its safety and efficacy as a supplement are not well-established.
Enzyme Assay
In vitro assays for 3'-adenylic acid are primarily biochemical rather than pharmacological. For nucleotide analysis, high-performance liquid chromatography (HPLC) with UV detection is used to quantify 3'-AMP in biological samples. Enzymatic assays using 3'-nucleotidase are used to measure enzyme activity: the enzyme is incubated with 3'-AMP in assay buffer (50 mM Tris-HCl, pH 7.4, 1 mM MgCl₂) and phosphate release is measured by colorimetric assays (e.g., Malachite Green). For receptor binding studies, competition assays using adenosine receptors may be performed, although 3'-AMP has low affinity for these receptors. For antioxidant activity, DPPH or ABTS assays may be used.
Cell Assay
In vitro cell-based assays for 3'-adenylic acid use various cell types including neurons, cardiomyocytes, and immune cells. Cells are cultured in appropriate media and treated with 3'-AMP at various concentrations (1-1000 μM) for 1-48 hours. Cell viability is assessed by MTT assays. Intracellular ATP levels are measured using luciferase-based assays. Adenosine release and metabolism are assessed by HPLC analysis of culture media. Effects on signaling pathways (e.g., cAMP, ERK, Akt) are assessed by Western blot. Inflammatory responses are evaluated by measuring cytokine production via ELISA. Neuroprotective effects are assessed in models of oxidative stress or excitotoxicity.
Animal Protocol
In vivo animal studies for 3'-adenylic acid are limited as it is not a therapeutic agent. Some studies have been conducted to evaluate its potential as a dietary supplement. In rodent models, the compound is administered orally or intraperitoneally at doses of 10-100 mg/kg. Parameters such as exercise performance, cognitive function, and cardiovascular function may be assessed. Blood and tissue samples are collected for analysis of nucleotide levels and metabolites. In models of ischemia or injury, the compound's protective effects may be evaluated. However, the evidence for therapeutic efficacy is limited, and the compound is not approved for clinical use.
ADME/Pharmacokinetics
3'-Adenylic acid is an endogenous nucleotide that is rapidly metabolized in vivo. Following administration, it is hydrolyzed by nucleotidases to adenosine, which is further metabolized by adenosine deaminase to inosine, and by adenosine kinase to AMP. The half-life of 3'-AMP in circulation is very short due to rapid metabolism. It is distributed to tissues where it participates in nucleotide metabolism. The compound does not cross the blood-brain barrier efficiently, but its metabolite adenosine does. Excretion is primarily in urine as uric acid and other metabolites. Specific pharmacokinetic data for 3'-AMP as a therapeutic agent are limited.
Toxicity/Toxicokinetics
3'-Adenylic acid is an endogenous metabolite and is generally considered safe at physiological concentrations. As a dietary supplement, it is generally recognized as safe (GRAS) at recommended doses. High doses may cause gastrointestinal discomfort, flushing, and other side effects related to adenosine signaling. The compound is not classified as a carcinogen, mutagen, or reproductive toxicant. However, as with any supplement, it should be used with caution in individuals with certain medical conditions (e.g., gout, kidney disease). This compound is for research use and as a dietary supplement ingredient. It is not approved as a therapeutic drug.
Additional Infomation
3'-AMP is an adenosine 3'-phosphate with a monophosphate group attached at the 3'-position. It is found in mice, humans, and E. coli as a metabolite. It is a combination of adenosine 3'-phosphate and purine ribonucleotide 3'-monophosphate. It is the conjugate acid of 3'-AMP(2-). 3'-AMP is a metabolite found or produced in E. coli strains K12 and MG1655. 3'-Adenosine has also been reported in fruit flies, sunflowers, and other organisms with relevant data. Adenine nucleotides have a phosphate group esterified at the 2', 3', or 5' position of their glycosyl group.
3'-Adenylic acid (CAS# 84-21-9), also known as adenosine 3'-monophosphate (3'-AMP), is a nucleotide consisting of adenine, ribose, and a phosphate group attached at the 3' position. It is a key component of RNA and is involved in various biological processes including cellular metabolism and signal transduction. It is an endogenous metabolite and is used in research to study nucleotide metabolism. It is also used as a dietary supplement ingredient. It is not approved as a therapeutic drug. This compound is for research use and as a dietary supplement, not for therapeutic use. Standard safety precautions should be followed when handling this compound.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Exact Mass
347.063
CAS #
84-21-9
PubChem CID
41211
Appearance
White to off-white solid powder
Density
2.3±0.1 g/cm3
Boiling Point
815.5±75.0 °C at 760 mmHg
Melting Point
-210ºC (dec.)
Flash Point
447.0±37.1 °C
Vapour Pressure
0.0±3.1 mmHg at 25°C
Index of Refraction
1.905
LogP
-1.46
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
4
Heavy Atom Count
23
Complexity
481
Defined Atom Stereocenter Count
4
SMILES
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)(O)O)O)N
InChi Key
LNQVTSROQXJCDD-KQYNXXCUSA-N
InChi Code
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
Chemical Name
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02318043 COMPLETED Drug: inhaled corticosteroids
(usually budesonide/fomorterol 160/4.5mcg;
fluticasone/salmeterol 250/50mcg)
Asthma Guangzhou Institute of Respiratory Disease 2007-01 Not Applicable
NCT03323827 UNKNOWN STATUS Obesity
Type 2 Diabetes Mellitus
University of Arizona 2016-11
NCT02391519 RECRUITING Procedure: Collection of myometrial,
cord blood, and placental tissue samples
IUGR
Preeclampsia
Pregnancy
University of Colorado, Denver 2016-01
NCT05032729 COMPLETED Other: Trypophan, Theanine and 5'AMP
Other: Placebo
Balance
Cognitive Performance
Physical Performance
Sleep
PepsiCo Global R&D 2022-03-14 Not Applicable
NCT01939587 COMPLETED Drug: PBF-680 5 mg
Drug: PBF-680 20 mg
Drug: Placebo
Asthma Fundació Institut de Recerca
de l'Hospital de la Santa Creu i Sant Pau
2013-12 Phase 2
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