Adenosine
- CAS No.
- 58-61-7
- Chemical Name:
- Adenosine
- Synonyms
- AR;(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;Adenosin;ADENINENUCLEOSIDE;Androgen receptor;2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;Adesine;Adenocard;Adenoscan;(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- CBNumber:
- CB7304660
- Molecular Formula:
- C10H13N5O4
- Molecular Weight:
- 267.24
- MOL File:
- 58-61-7.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/28 13:53:26
| Melting point | 234-236 °C (lit.) |
|---|---|
| Boiling point | 410.43°C (rough estimate) |
| alpha | D11 -61.7° (c = 0.706 in water); 9D -58.2° (c = 0.658 in water) |
| Density | 1.3382 (rough estimate) |
| refractive index | 1.7610 (estimate) |
| storage temp. | 2-8°C |
| solubility | Slightly soluble in water, soluble in hot water, practically insoluble in ethanol (96 per cent) and in methylene chloride. It dissolves in dilute mineral acids. |
| form | Crystalline Powder |
| pka | 3.6, 12.4(at 25℃) |
| color | White |
| PH | 3.59；12.5 |
| optical activity | [α]20/D 70±3°, c = 2% in 5% NaOH |
| Water Solubility | Soluble in water, ammonium hydroxide and dimethyl sulfoxide. Insoluble in ethanol. |
| λmax | 257 (pH 1)；260 (pH 6) |
| Merck | 14,153 |
| BRN | 93029 |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| InChIKey | OIRDTQYFTABQOQ-KQYNXXCUSA-N |
| LogP | -0.755 (est) |
| CAS DataBase Reference | 58-61-7(CAS DataBase Reference) |
| NIST Chemistry Reference | adenosine(58-61-7) |
| EPA Substance Registry System | Adenosine (58-61-7) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P305+P351+P338 | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 24/25-36/37/39-26 | |||||||||
| WGK Germany | 2 | |||||||||
| RTECS | AU7175000 | |||||||||
| F | 10-23 | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29389090 | |||||||||
| Toxicity | LD50 oral in mouse: > 20gm/kg | |||||||||
| NFPA 704 |
|
Adenosine price More Price(20)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A9251 | Adenosine ≥99% | 58-61-7 | 5G | ₹2316.55 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9251 | Adenosine ≥99% | 58-61-7 | 1G | ₹2338.2 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9251 | Adenosine ≥99% | 58-61-7 | 25G | ₹6137.78 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1138 | Adenosine Pharmaceutical Secondary Standard; Certified Reference Material | 58-61-7 | 1G | ₹8995.58 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9251 | Adenosine ≥99% | 58-61-7 | 100G | ₹20145.33 | 2022-06-14 | Buy |
Adenosine Chemical Properties,Uses,Production
Chemical Properties
Adenosine is an important nucleoside composed of adenine and ribose. White, crystalline, odorless powder, mild, saline, or bitter taste, quite soluble in hot water, practically insoluble in alcohol. Formed by isolation following hydrolysis of yeast nucleic acid.
Uses
adenosine is an amino acid. Studies indicate anti-wrinkle and skinsmoothing capacities. Although little is written about its direct skin benefit, adenosine plays an important role in biochemical processes. As adenosine triphosphate (ATP) and adenosine diphosphate (ADP), it is involved in energy transfer, and as cyclic adenosine monophosphate (cAMP) in signal transduction.
Definition
ChEBI: Adenosine is a ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. It has a role as an anti-arrhythmia drug, a vasodilator agent, an analgesic, a human metabolite and a fundamental metabolite. It is a purines D-ribonucleoside and a member of adenosines. It is functionally related to an adenine.
Origin
Adenosine may be generated intracellularly in the central nervous system from degradation of AMP or from the hydrolysis of S-adenosyl homocysteine, and then exit via bi-directional nucleoside transporters, or extracellularly by the metabolism of released nucleotides. Inactivation of extracellular adenosine occurs by transport into neurons or neighboring cells, followed by either phosphorylation to AMP by adenosine kinase or deamination to inosine by adenosine deaminase[1].
Biological Functions
[1] Mercedes Garcia-Gil. “Metabolic Aspects of Adenosine Functions in the Brain.” Frontiers in Pharmacology (2021): 672182.
Biological Functions
Adenosine regulates multiple physiological and pathophysiological processes, by acting both through G-protein coupled adenosine receptors and intracellularly. It modulates neuronal plasticity, astrocytic activity , learning and memory, food intake, motor function, sleep/wake cycle, pain, immunosupression, proliferation, and aging. Adenosine is involved in ischemia and stroke, epilepsy, and neurodegenerative pathologies such as Parkinson's disease (PD), Alzheimer's disease (AD), amyotrophic lateral sclerosis (ALS), and Huntington's disease (HD). Extracellular adenosine, interacting with P1 receptors (A1R, A2AR, A2BR, and A3R) regulates metabolism through different signaling pathways[1].
General Description
Adenosine is a purine nucleoside and a building block of RNA and many other biomolecules such as adenosine triphosphate and nicotinamide adenine dinucleotide. In the extracellular space, ecto-5′-nucleotidase (CD73) dephosphorylates adenosine triphosphate (ATP) to produce adenosine. Adenosine has four receptors namely A1R, A2AR A2BR and A3R. Adenosine plays a key role in the osteogenic differentiation. A1R induces osteoclast differentiation and A2AR induces osteoblast differentiation.
Biological Activity
Neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes.
Clinical Use
Adenosine (Adenocard) is an endogenous nucleoside
that is a product of the metabolism of adenosine triphosphate.
It is used for the rapid termination of supraventricular
arrhythmias following rapid bolus dosing.
Adenosine is approved for the acute management and
termination of supraventricular tachyarrhythmias, including A-V nodal reentrant tachycardia and A-V reciprocating
tachycardia. Adenosine may be helpful in the
diagnosis of atrial flutter.
Side effects
Adverse reactions to the administration of adenosine are fairly common; however, the short half-life of the drug limits the duration of such events.The most common adverse effects are flushing, chest pain, and dyspnea. Adenosine may induce profound bronchospasm in patients with known reactive airway disease. The mechanism for bronchospasm is unclear, and the effect may last for up to 30 minutes despite the short half-life of the drug.
Drug interactions
Metabolism of adenosine is slowed by dipyridamole, indicating that in patients stabilized on dipyridamole the therapeutically effective dose of adenosine may have to be increased. Methylxanthines antagonize the effects of adenosine via blockade of the adenosine receptors.
Purification Methods
Crystallise adenosine from distilled water and dry it at 110o. It has been purified via the picrate, where ethanolic picric acid is added to adenosine and the picrate is filtered off and recrystallised from EtOH. It has m 180-185o(dec). Adenosine is recovered by dissolving 0.4g of the picrate in 80mL of hot H2O, treated with a small quantity of Dowex 1 anion exchange resin in the chloride form, and the resin is filtered off. The filtrate is treated with more resin and filtered again. One equivalent of aqueous NaOH is added to the colourless filtrate which is evaporated to 4mL and cooled to give 0.176g of adenosine m 236o. [Davoll et al. J Chem Soc 967 1948, Davoll & Lowy J Am Chem Soc 73 1650 1951, Beilstein 26 III/IV 3598.]
Precautions
Patients with second- or third-degree A-V block should not receive adenosine. As indicated previously, the use of adenosine in asthmatic patients may exacerbate the asthmatic symptoms.
Adenosine Preparation Products And Raw materials
Raw materials
Preparation Products
1of2
chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| JSK Chemicals | +919879767970 | Gujarat, India | 3756 | 58 | Inquiry |
| Surajlok Chemicals Pvt Ltd (Neon Laboratories Ltd) | +91-2268107000 +91-9987232509 | Maharashtra, India | 30 | 58 | Inquiry |
| Bioaltus Laboratories Pvt Ltd | +91-2249744539 +91-9820139885 | Maharashtra, India | 34 | 58 | Inquiry |
| ALPHA CHEMIKA | +91-22-22061123 +91-22-66382501 | Mumbai, India | 1681 | 43 | Inquiry |
| Scientific OEM | +91-22- 2343 7546 / 2341 3094 | New Delhi, India | 1996 | 38 | Inquiry |
| Kiran Lights Laboratories | 91-9987701501 | Maharashtra, India | 262 | 58 | Inquiry |
| A. R. Life Sciences Private Limited | 09985733315 | Hyderabad, India | 33 | 58 | Inquiry |
| Athos Chemicals | 91-9998858909 | Gujarat, India | 315 | 58 | Inquiry |
| Kemona Impex | 08068441141Ext 577 | Mumbai, India | 221 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| Supplier | Advantage |
|---|---|
| JSK Chemicals | 58 |
| Surajlok Chemicals Pvt Ltd (Neon Laboratories Ltd) | 58 |
| Bioaltus Laboratories Pvt Ltd | 58 |
| ALPHA CHEMIKA | 43 |
| Scientific OEM | 38 |
| Kiran Lights Laboratories | 58 |
| A. R. Life Sciences Private Limited | 58 |
| Athos Chemicals | 58 |
| Kemona Impex | 58 |
| CHEMSWORTH | 30 |
Related articles
- The Biological activity, Drug Interactions, and Contraindications of Adenosine.
- Adenosine is a ubiquitous extracellular signaling molecule and plays a fundamental role in the regulation of coronary microcir....
- Nov 17，2023
- Adenosine: Physiology, Clinical Applications and Safety
- Adenosine is a nucleoside involved in cellular function. It has antiarrhythmic effects, potential cardioprotective properties,....
- Jul 13，2023
- Application and Pharmacology of Adenosine
- Adenosine is a ribonucleoside comprised of adenine bound to ribose, with vasodilatory, antiarrhythmic and analgesic activities....
- Jun 20，2022
Related Qustion
- Q:What does adenosine do for your body?
- A:Adenosine terminates AV nodal-dependent arrhythmias like atrioventricular nodal reentrant tachycardia (AVNRT) and atrioventric....
- Aug 27，2024
58-61-7(Adenosine)Related Search:
1of4
chevron_right