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Adenosine 5'-monophosphate structure

Adenosine 5'-monophosphate

  • CAS:61-19-8
  • MW:347.221221
  • MF:C10H14N5O7P
antiasthmatic
 
1. Names and Identifiers
1.1 Name
Adenosine 5'-monophosphate
1.2 Synonyms
)-monophosphate disodium salt (mixed isomers); [(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]methyl dihydrogen phosphate; 3-Hydroxy Tibolone-d5 |(mixture of 3αadenosine5’-phosphate; 4-PREGNEN-18-OL, 3, 20-DIONE (20αOLS) 18, 20-HEMIKETAL; 5'-Adenylic acid; 5'-AMP; 9-(5-O-Phosphono-α-D-lyxofuranosyl)-9H-purin-6-amine; 9H-Purin-6-amine, 9-(5-O-phosphono-α-D-lyxofuranosyl)-; Adenosine -5'- Monophosphate(AMP-H); adenosine 5″-monophosphate; Adenosine 5'-phosphoric acid; adenosine,mono(dihydrogenphosphate)(ester); adenosine-5″-monophosphate; Adenosine-5'-monophosphate; ADENOSINE-5'-MONOPHOSPHORIC ACID; Adenosine-5'-phosphoric Acid; Ado-5'-P; MFCD00005750; phosphate d'adénosine; phosphate d'adenosine; t-Adenylic Acid;
1.3 CAS No.
61-19-8
1.4 CID
6083
1.5 EINECS
200-500-0
1.6 Molecular Formula
C10H14N5O7P
1.7 Inchi
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
1.8 InChkey
UDMBCSSLTHHNCD-KQYNXXCUSA-N
1.9 Canonical Smiles
C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N
1.10 Isomers Smiles
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
2. Properties
2.1 Solubility
H2O: with addition of mild alkalisoluble
2.2 Appearance
white crystalline powder
2.3 Storage
Keep Cold.
2.4 Chemical Properties
White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether.
2.5 Color/Form
Powder
2.6 pKa
3.8, 6.2(at 25℃)
2.7 Water Solubility
H2O: with addition of mild alkalisoluble
2.8 Spectral Properties
SPECIFIC OPTICAL ROTATION: -26 DEG @ 20 DEG C/D (C= 2, 10% HCL); & -47.5 DEG @ 20 DEG C/D (C= 2, 2% NAOH)
MAX ABSORPTION (WATER, PH= 1.1): 255 NM (LOG E= 4.16); SPECIFIC OPTICAL ROTATION: -41.78 DEG @ 50 DEG C/D (WATER)
IR: 14657 (Sadtler Research Laboratories Prism Collection)
UV: 8-173 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
2.9 Stability
FREE ACID & ITS SALTS ARE STABLE FOR LONG PERIODS IN DRY STATE; NEUTRAL SOLN ARE ALSO STABLE
2.10 StorageTemp
Keep in dark place,Inert atmosphere,Room temperature
3. Use and Manufacturing
3.1 Definition
ChEBI: A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.
3.2 Description
White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether. colorless to white crystalline powder
3.3 Usage
antiasthmatic
4. Safety and Handling
4.1 Safety Profile
Slightly toxic byintraperitoneal route. Experimentalreproductive effects. Human mutation datareported. When heated to decomposition itemits toxic fumes of PO, and NOx. Adenosine 5'-monophosphate Preparation Products And Raw materials Preparation Products
4.2 Report

AMP is reported in EPA TSCA Inventory.

4.3 Safety

Slightly toxic by intraperitoneal route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of POx and NOx.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: AU7480500

4.4 Specification

?AMP (CAS NO.61-19-8), its Synonyms are Adenosine 5'-phosphate ; Adenosine monophosphate ; Adenosine phosphate ; 5'-AMP ; 5'-Adenylic acid ; A5MP ; Adenosine 5'-(dihydrogen phosphate) ; Adenosine 5'-monophosphate ; Adenosine 5'-monophosphoric acid ; Ergadenylic acid ; Fosfato de adenosina ; Monophosphadenine ; Muscle adenylic acid ; Muskeladenosin-phosphorsaeure ; Muskeladenylsaeure ; My-B-Den ; Myoston . It is colorless to white crystalline powder.

4.5 Toxicity
1. ???

oms-hmn:oth 100 μmol/L

??? JIDEAE ?? Journal of Investigative Dermatology. 65 (1975),52.
2. ???

oms-mus:oth 50 μmol/L

??? JIDEAE ?? Journal of Investigative Dermatology. 66 (1976),313.
3. ???

ipr-mus LD50:4?g/kg

??? PCJOAU ?? Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 20 (1986),160.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum
13C NMR : in CDCl3  
13C NMR : Predict  
1H NMR : 400 MHz in D2O  
1H NMR : Predict  
Predict 1H proton NMR  
IR : KBr disc  
IR : nujol mull  
7. Synthesis Route
61-19-8Total: 97 Synthesis Route
 
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8. Precursor and Product
precursor:
product:
9. Computed Properties
10.Other Information
Usage
a useful ligand determinant that facilitate the binding of APS reductase inhibitors and activates adenosine receptor agonists. 5?-AMP is an activator of a class of protein kinases known as AMP-activated protein kinase, an activator of phosphorylase b in the polymerization reaction for the synthesis of branched polysaccharides, a reagent in the synthesis of adenosine-5?-phosphoimidazolide, an inhibitor of endogenous NMN adenylyltransferase (NMNAT) activity that converts NMN to NAD+.
Merck
14,158
Chemical Properties
White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether.
Applications
Clinically it is used to treat disseminated sclerosis, porphyria, itching, liver disease, varicose ulcer complication. Eye drops with denosine monophosphate as the main component can be used to treat eye fatigue, central amphiblestitis, ocular pannus,  herpes and other corneal surface diseases. Intramuscular injection shows local erythema, generalized essential telangiectasia, red face, dizziness, breathing difficulty and palpitation.
As nutrition enhancer; as intermediate to produce nucleotide drugs; as food additive; as biological products; as dietary supplement and biochemical reagent. It is used to produce adenosine triphosphate (ATP), cyclic adenylate (cAMP) and other biochemical drugs. It is a type of nucleotide products and to produce antiviral drugs, synthetic energy drugs and cardiovascular and cerebrovascular drugs, such as adenosine, ATP, 3 '-5'-cyclic adenosine monophosphate.
Preparation
Candida utilis fungi is treated with hot water to obtain nucleic acids, which is hydrolyzed by enzymes and separated to obtain the final product.
Take mycelia as the raw material:
Subtraction and sedimentation of mycelia are carried out with 3 times amount of water. Industry base is added to reach a base concentration of 0.25% (g/100mL). After stirring for 1 hours, 20% sulfuric acid is added until the PH value is 7. The solution is filtrated and the pH value of filtrate is adjusted with 20% sulfuric acid to 2.5. Centrifugation is then applied to obtain nucleic acid mud.
mycelia [sodium hydroxide]→[1h] extract solution [20% sulfuric acid] → [pH=7, filtration] filtrate [20% sulfuric acid] →[pH=2.5, centrifugation] nucleic acid mud
1% nucleic acid solution is made by subsequent dissolution, enzymolysis, absorption and elution. 10% ammonia water is then used to adjust the pH value to 6-6.2. Then the mixture is heated at 90°C for 20 min and cooled. After centrifugation, the supernatant is heated up to 65-70°C and added with 1/3 phosphodiesterase solution. After 2 hours, the temperature is raised to 90°C.  10min later, it is cooled to room temperature. 20% sulfuric acid is added to adjust the pH value to 2.5-3. After filtration, the filtrate is adjusted with ammonia solution until the pH=7.2-7.5. 0.3% (3 g/L) diatomite is then added to assist the filtration. The corresponding supernatant is filtered with an anion exchange resin column (717-type) and eluted with 0.05 mol/L sulfuric acid. Afterwards, absorption, elution and crystallization are carried out. The detailed procedures of these three steps are:
The eluate is first absorbed with a cation exchange column (732-type) and eluted with distilled water (pH=1.5). The collection of eluate starts when the eluate turned red with bromine water. The eluate is then concentrated to 80-90 mg/mL under reduced pressure, added with diatomite and stirred for 30 min before filtration. The filtrate is adjusted with 6 mol/L hydrochloric acid till pH=2.5. To realize full crystallization, the filtrate is cooled during stirring. After followed filtration, it is washed with dry ethanol for 3 times. Vacuum drying at 60°C is applied to obtain the final AMP products.
Nucleic acid mud [ammonia gas] →[pH=6-6.2, 90°C, 20min] supernatant [phosphodiesterase] →[65-70°C,2h,] hydrolysis solution [717 resin] →absorbent [sulfuric acid] →elution solution [732 resin] →AMP, CMP, GMP absorbent mixtures.
Usage restriction
GB 2760-2001:infant formula milk powder 0.2~0.58 g/kg (based on the total amount of nucleotide)
Category
Toxic substance
Toxicity Grading
Middle toxicity
Acute Toxicity
Peritoneal-mouse LD50: 4000 mg/kg
Flammability Hazardous Characteristics
Flammable; generation of toxic nitrogen oxides and phosphorous oxide smoke when heated.
Storage and Transport
Stored in well ventilated area, low temperature, and dry.
Extinguishing Agent
Dry powder, foam, sand, carbon dioxide.
Chemical Properties
colorless to white crystalline powder
Uses
antiasthmatic
Uses
vasodilator, neuromodulator
Uses
Adenosine 5'-Monophosphate is a natural occurring nucleotide and a useful ligand determinant that facilitate the binding of APS reductase inhibitors and activates adenosine receptor agonists.
Uses
A useful ligand determinant that facilitates the binding of APS reductase inhibitors.
Uses
Adenosine 5'-monophosphate is a nucleotide (building blocks of nucleic acid) added to skin care products to bind water and moisture.
Definition
ChEBI: A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.
Brand name
Adenyl (Wyeth-Ayerst); My-BDen (Bayer.
Safety Profile
Slightly toxic by intraperitoneal route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of PO, and NOx.
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12. Related Questions
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