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Adenosine
Cas No: 58-61-7
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58-61-7 Usage

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.]

In the body

Adenosine in the body Function
Brain Promoting sleep and suppresses arousal acting as a central nervous system depressant.
Heart Causing dilation of the coronary blood vessels that Improving blood circulation to the heart; Increasing the diameter of blood vessels in the peripheral organs; Decreasing heart rate
Blood Broken down by adenosine deaminase. By taking medicine like Dipyridamole(inhibitor of adenosine deaminase), it can improve blood flow through the coronary blood vessels that supply the heart muscles.
Kidneys, lungs and liver In the kidneys adenosine decreases renal blood flow and decrease the production of rennin from the kidneys. In the lungs it causes constriction of airways and in the liver it leads to constriction of blood vessels and increases breakdown of glycogen to form glucose.

Mechanism of action

Its function is realized through the activation of the adenosine receptor (A receptor). Adenosine activates G protein coupled potassium channels by binding to the A receptor which makes increasing the outflow of K+ and cell membrane hyperpolarization so as to decrease the automaticity in the atrium, sinoatrial node and atrioventricular node. It can also significantly increase the level of cGMP , prolong ERP of the atrioventricular node and slowing of atrioventricular, depress sympathetic nervous or early and delayed after depolarization induced by isoproterenol and then plays an effective role in arrhythmia. This product has not been classified in I~IV anti arrhythmia medicine.

Adenosine receptor
  • A1 receptors, which are found in cardiomyocytes and which are responsible for the inhibition of adenylyl cylase activity which lowers cyclic adenosine monophosphate (AMP) results in sinus slowing, increase in AV node conduction delay, and antagonism of the effects of catecholamines;
  • A2 receptors, which are found in endothelial cells and vascular smooth muscle and are responsible for the enhancement of adenylyl cylase activity and increased cyclic AMP which relaxes smooth muscle. Both negative chronotropic and dromotropic effects of adenosine are cyclic AMP independent (direct action) as well cyclic AMP dependent (indirect action).

Uses

antiarrhythmic, cardiac depressant

Medical uses

Adenosine has a role in the expansion of coronary artery and myocardial contractility, is clinically applied in the treatment of angina, hypertension, cerebrovascular disorders, stroke sequelae, muscular atrophy, etc. It is also given intravenously (by IV) for treating supraventricular tachycardia and Tl myocardial imaging. It is also used for cardiac stress tests.   Side effects:
Since the half-life of this compound is less than 10 seconds, its side effects are usually transient. However, side effects are common, and include flushing, headache, chest discomfort, bronchoconstriction, and occasionally hypotension. Hepatic and renal failure and other drugs except dipyridamole seem to have little effect on the action of adenosine.     Adenosine dose

   

Chemical Properties

White crystalline powder

Brand name

Adenocard (Astellas); Adenoscan (Astellas).

Biological Activity

Neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes.

Defination

Adenosine is a natural nucleotide, which is the intermediate product of metabolism, chemically 6-amino-9-beta-D-ribofuranosyl-9-H-purine. Adenosine is one of the important active components in the body, helps in cellular energy transfer by forming molecules like adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signaling various pathways and functions in the body by forming signally molecules like cyclic adenosine monophosphate (cAMP).

Definition

ChEBI: A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta1N9-glycosidic bond.

Uses

Nucleotide.
InChI:InChI=1/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6+,7+,10+/m1/s1

58-61-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (01890)  Adenosine   58-61-7 01890-100G 3,143.79CNY Detail
Sigma (01890)  Adenosine   58-61-7 01890-25G 1,338.48CNY Detail
Sigma (01890)  Adenosine   58-61-7 01890-5G 389.61CNY Detail
Sigma (A9251)  Adenosine  ≥99% 58-61-7 A9251-100G 2,514.33CNY Detail
Sigma (A9251)  Adenosine  ≥99% 58-61-7 A9251-25G 969.93CNY Detail
Sigma (A9251)  Adenosine  ≥99% 58-61-7 A9251-5G 349.83CNY Detail
Sigma (A9251)  Adenosine  ≥99% 58-61-7 A9251-1G 188.37CNY Detail
USP (1012123)  Adenosine  United States Pharmacopeia (USP) Reference Standard 58-61-7 1012123-200MG 4,588.74CNY Detail
Sigma-Aldrich (A0230200)  Adenosine  European Pharmacopoeia (EP) Reference Standard 58-61-7 A0230200 1,880.19CNY Detail
Sigma-Aldrich (PHR1138)  Adenosine  pharmaceutical secondary standard; traceable to USP and PhEur 58-61-7 PHR1138-1G 732.19CNY Detail
Alfa Aesar (A10781)  Adenosine, 99%    58-61-7 250g 4410.0CNY Detail
Alfa Aesar (A10781)  Adenosine, 99%    58-61-7 50g 1006.0CNY Detail

58-61-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name adenosine

1.2 Other means of identification

Product number -
Other names Adenine riboside

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-61-7 SDS

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