Adenosin

Adenosine Struktur
58-61-7
CAS-Nr.
58-61-7
Bezeichnung:
Adenosin
Englisch Name:
Adenosine
Synonyma:
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
Summenformel:
C10H13N5O4
Molgewicht:
267.24
MOL-Datei:
58-61-7.mol

Adenosin Eigenschaften

Schmelzpunkt:
234-236 °C (lit.)
Siedepunkt:
410.43°C (rough estimate)
alpha 
D11 -61.7° (c = 0.706 in water); 9D -58.2° (c = 0.658 in water)
Dichte
1.3382 (rough estimate)
Brechungsindex
1.7610 (estimate)
storage temp. 
2-8°C
Löslichkeit
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.
Aggregatzustand
Crystalline Powder
pka
3.6, 12.4(at 25℃)
Farbe
White
Optische Aktivität
[α]20/D 70±3°, c = 2% in 5% NaOH
Wasserlöslichkeit
Soluble in water, ammonium hydroxide and dimethyl sulfoxide. Insoluble in ethanol.
Merck 
14,153
BRN 
93029
Stabilität:
Stable. Incompatible with strong oxidizing agents.
InChIKey
OIRDTQYFTABQOQ-KQYNXXCUSA-N
LogP
-0.755 (est)
CAS Datenbank
58-61-7(CAS DataBase Reference)
NIST chemische Informationen
adenosine(58-61-7)
EPA chemische Informationen
Adenosine (58-61-7)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
R-Sätze: 36/37/38
S-Sätze: 24/25-36/37/39-26
WGK Germany  2
RTECS-Nr. AU7175000
10-23
TSCA  Yes
HS Code  29389090
Giftige Stoffe Daten 58-61-7(Hazardous Substances Data)
Toxizität LD50 oral in mouse: > 20gm/kg
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
Sicherheit
P261 Einatmen von Staub vermeiden.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Adenosin Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:

S24/25:Berührung mit den Augen und der Haut vermeiden.

Chemische Eigenschaften

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.

Verwenden

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.

Biologische Funktion

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].

Allgemeine Beschreibung

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.

Biologische Aktivität

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.

Nebenwirkungen

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.

Arzneimittelwechselwirkung

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.

läuterung methode

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.]

Vorsichtsmaßnahmen

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.

Adenosin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Adenosin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 999)Lieferanten
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58-61-7(Adenosin)Verwandte Suche:


  • D-ADENOSINE
  • (2R,3R,4S,5R)-2-(6-AMINO-PURIN-9-YL)-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-3,4-DIOL
  • 9-BETA-D-RIBOFURANOSYLADENINE
  • Adenine riboside, Adenine-9-beta-ribofuranoside
  • ADENOSINE extrapure for biochemistry
  • ADENINE RIBOSIDE
  • ADENOSINE
  • ADENINE-9-BETA-D-RIBOFURANOSIDE
  • 6-Amino-9-β-D-ribofuranosyl-[9H]-purine
  • ADENOSINE(FREE BASE)(RG)
  • adenine-9-1'-β-ribofuranoside
  • vidarabine,ara-A
  • 9-D-Ribofuranosyl sdenine
  • ADENOSINE[9-BETA-D-RIBOFURANOSYLADENINE]
  • Adenoside
  • Sandesin
  • USAF cb-10
  • usafcb-10
  • 9-β-D-Ribofuranosyladenine
  • adenosine free base
  • ADENOSINE: H2O
  • Adenosine for Injection
  • 1-(6-AMino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranose
  • Adenogesic
  • Adrekar
  • NSC 7652
  • Adenosine, 99+% 25GR
  • Adenosine, 99+% 5GR
  • 15N5, 96-98%)
  • ADENOSINE:H2O (15N5, 96-98%)
  • GUANOSINE:H2O (13C10, 98%
  • ANTI-ANDROGEN RECEPTOR (ANDR) antibody produced in rabbit
  • Anti-AKR1B1, C-Terminal antibody produced in rabbit
  • Human Amphiregulin ELISA Kit
  • ADENOSINE (Ado)
  • adenosin (german)
  • MONOCLONAL ANTI-ANDROGEN RECEPTOR PROTEIN antibody produced in mouse
  • Adenosine Vetec(TM) reagent grade, 98%
  • ATP DISODIUM TRIHYDRATE ULTRA PURE GRADE
  • Adenine riboside, low endotoxins
  • Adenine-9-β-D-ribofuranoside, low endotoxis
  • Adenosine free base, low endotoxinsCell culture grade, ≥ 99.5% (HPLC)
  • ADENINE-9-D-RIBOFURANOSIDE
  • Adenine-9-B-D-Ribofuranoside
  • (-)-ADENOSINE, 99+%
  • ADENOSINE FREE BASE CELL CULTURE TESTED
  • Adenine-9-β-D-ribofur
  • AdenosineForBiochemistry
  • Adenosine,>98%
  • 9-bate-D-Ribofuranosyladenine free base
  • Adenosine,9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside
  • Adenosine (200 mg)
  • 6-amino-9-beta-d-ribofuranosyl-9h-purine
  • 6-Amino-9beta-D-ribofuranosyl-9H-purine
  • 9-beta-D-Ribofuranosidoadenine
  • 9-beta-D-Ribofuranosyl-9H-purin-6-amine
  • 9H-Purin-6-amine, 9-beta-d-ribofuranosyl-
  • Adenocor
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