AMP directly activates AMP-activated protein kinase (AMPK). It acts as a substrate for prostatic acid phosphatase (PAP), which dephosphorylates it to adenosine, subsequently activating A1 adenosine receptors in the dorsal spinal cord. In the glycolytic pathway, AMP serves as an allosteric regulator, reversing the ATP-mediated inhibition of phosphofructokinase.

The result of numerous enzymatic processes, many of which are dysregulated in pathological situations, is adenosine monophosphate [1].

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In isolated guinea pig taenia coli, AMP induces concentration-dependent smooth muscle relaxation, although its activity is weaker than that of ATP. In isolated bone cell systems, AMP is converted to adenosine by alkaline phosphatase. Metabolism of AMP in the supernatant of cultured chronic lymphocytic leukemia cells can be quantitatively monitored using reversed-phase HPLC.

The in vivo activity of oral AMP has been demonstrated in several animal models. In high-fat diet-fed C57BL/6J mice receiving AMP (13 mg/L) via drinking water, significant improvements in oral glucose tolerance test (OGTT) and insulin tolerance test (ITT) were observed, associated with AMP-induced upregulation of AMPK phosphorylation in skeletal muscle. Dietary AMP supplementation (0.1%) in C57BL/6 mice increased food intake, enhanced brown adipose tissue thermogenesis, promoted white adipose tissue lipolysis, and increased oxygen consumption and energy expenditure. In an LPS-induced lung inflammation mouse model, [³H]-labeled AMP uptake was significantly higher in normal lung tissue (49.7 %ID/g) than in inflamed lung tissue (28.9 %ID/g), suggesting AMP as a potential imaging marker for normal lung function.

A reversed-phase high-performance liquid chromatography (RP-HPLC) method is used. A silica-based reversed-phase column is employed with a binary mobile phase consisting of 7 mM ammonium acetate and acetonitrile at a flow rate of 1.00 ml/min at room temperature. Eluates are monitored with a photodiode array UV detector at 260 nm. AMP, inosine (INO), and adenosine (ADO) elute at approximately 7, 11, and 11.9 min, respectively, with a total run time of 20 min per sample. Quantification is performed using standard calibration curves.

Using human chronic lymphocytic leukemia (CLL) cells, purified cells are cultured in serum-free medium, and supernatant samples are collected at various time points. After simple pretreatment (serum-free medium eliminates the need for acetonitrile protein precipitation), the supernatant is analyzed by RP-HPLC to quantify extracellular AMP, ADO, and INO. System control, data acquisition, and analysis are performed using dedicated software. This sensitive and specific method is applicable to both suspension and adherent cell lines.

High-fat diet-induced C57BL/6J mice (7 weeks old) are administered AMP at a concentration of 13 mg/L via drinking water ad libitum for 14 or 25 weeks (concurrently with high-fat diet). An oral glucose tolerance test (OGTT) is conducted at 21 weeks of age after a 16-hour fast, and an insulin tolerance test (ITT) is performed at 22 weeks of age after a 3-hour fast. Blood and skeletal muscle samples are collected at the end of the experiment for serum parameter analysis and gene/protein expression assessment, respectively.

Absorption, Distribution and Excretion
Following oral administration of amphetamine to rats, it is completely recovered from the bloodstream. It appears rapidly in the blood (within 15–30 minutes) and distributes rapidly, as plasma concentrations decrease fivefold within 2 hours.

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Following a single oral dose of 14C-labeled AMP (10 mg/kg) in rats, the AMP molecule crosses the intestinal barrier intact to enter the bloodstream. In isolated vascularly perfused rat small intestine, AMP is quantitatively metabolized to end products (primarily uric acid) within 15 minutes of administration. Uric acid is the primary metabolite recovered from portal circulation. Intravenously administered AMP distributes from the circulation via cellular uptake, primarily by erythrocytes.

The acute intraperitoneal LD50 of AMP in mice is 4 g/kg. Intraperitoneal administration of 2800 mg/kg in rats during days 7–13 post-fertilization results in embryo/fetal toxicity (e.g., stunted development), with similar reproductive toxicity observed in mice at the same dose. The FDA has withdrawn approval for AMP, citing that it is neither safe nor effective for its intended uses as a vasodilator and anti-inflammatory agent. Too-rapid intravenous administration or inadvertent intramuscular injection into a vein can cause life-threatening arrhythmias.

[1]. Mondal S, et al. Utility of Adenosine Monophosphate Detection System for Monitoring the Activities of Diverse Enzyme Reactions. Assay Drug Dev Technol. 2017 Oct/Nov;15(7):330-341.

Adenanthin 5'-monophosphate is a purine nucleoside 5'-monophosphate with the nucleobase adenine. It has multiple functions, including as an EC 3.1.3.11 (fructose diphosphatase) inhibitor, an EC 3.1.3.1 (alkaline phosphatase) inhibitor, an Adenanthin A1 receptor agonist, a nutritional supplement, a micronutrient, a basic metabolite, and a cofactor. It is both Adenanthin 5'-phosphate and a purine nucleoside 5'-monophosphate. It is the conjugate base of Adenanthin 5'-monophosphate (1+). It is the conjugate acid of Adenanthin 5'-monophosphate (2-). Adenanthin phosphate, or Adenanthin acid, is an adenine nucleotide in which a phosphate group is esterified at the 2', 3', or 5' position of the sugar moiety. Because Adenanthin phosphate was considered neither safe nor effective, it was withdrawn by the U.S. Food and Drug Administration (FDA) because it was not suitable for its intended use as a vasodilator and anti-inflammatory agent.
Adenanthin monophosphate (AMAP) is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain).
AMAP has been reported in Drosophila melanogaster, silkworm, and other organisms with relevant data.
AMAP is a metabolite found in or produced by Saccharomyces cerevisiae.
Adenine nucleotides have a phosphate group esterified at the 2', 3', or 5' position of their sugar moiety.
See also: Poly AU (monomer).
Pharmacological Indications
For nutritional supplementation, and also for the treatment of dietary deficiencies or imbalances.
Mechanism of Action
Nucleotides such as Adenanthin-5'-monophosphate affect a variety of immune functions, including reversing immunosuppression caused by malnutrition and starvation, enhancing T cell maturation and function, enhancing natural killer cell activity, improving delayed-type hypersensitivity reactions, enhancing resistance to infectious pathogens such as Staphylococcus aureus and Candida albicans, and regulating the response of T cells to type 1 CD4 helper lymphocytes (Th1 cells). Studies have shown that mice fed a nucleotide-free diet exhibit impaired humoral and cellular immune responses. Supplementation with dietary nucleotides can restore both immune responses to normal. These studies used RNA (the delivery form of nucleotides) and ribonucleotides. The mechanism by which nucleic acids/nucleotides enhance immune activity remains unclear.

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Therapeutic Uses
Energy-rich phosphates are the "energy pool" for cells to obtain energy. Specific assays of nucleotides have diagnostic value in pathological conditions involving altered metabolism and are increasingly used in the diagnosis of heart, liver, and kidney diseases.

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Pharmacodynamics
Adenanthin monophosphate (AMP), also known as 5'-Adenanthin, is a nucleotide found in RNA. It is an ester formed from a phosphate group and the nucleoside Adenanthin. AMP consists of a phosphate group, a pentose ribose, and the nucleobase adenine. AMP can be used as a dietary supplement to enhance immune activity and as a sugar substitute to help maintain a low-calorie diet.

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C10H14N5O7P

347.2212

347.063

61-19-8

24937-83-5

6083

CRYSTALS FROM WATER + ACETONE
POWDER, NEEDLES FROM WATER & DIL ALC

2.3±0.1 g/cm3

798.5±70.0 °C at 760 mmHg

196-200 °C ; 195 °C

436.7±35.7 °C

0.0±3.0 mmHg at 25°C

1.905

-0.22

5

11

4

23

481

4

P(=O)(O[H])(O[H])OC([H])([H])[C@]1([H])[C@]([H])([C@]([H])([C@]([H])(N2C([H])=NC3=C(N([H])[H])N=C([H])N=C23)O1)O[H])O[H]

UDMBCSSLTHHNCD-KQYNXXCUSA-N

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(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

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~16.67 mg/mL (~48.01 mM)
H2O : ~1.67 mg/mL (~4.81 mM)

Solubility in Formulation 1: ≥ 1.67 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 1.67 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 1.67 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 4: 3.33 mg/mL (9.59 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

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