Adenosine

Modify Date: 2024-01-02 14:57:00

Adenosine Structure
Adenosine structure
 Common Name Adenosine
CAS Number 58-61-7 Molecular Weight 267.241
Density 2.1±0.1 g/cm3 Boiling Point 676.3±65.0 °C at 760 mmHg
Molecular Formula C10H13N5O4 Melting Point 234-236ºC
MSDS Chinese USA Flash Point 362.8±34.3 °C

 Use of Adenosine


Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond.Target: Nucleoside antimetabolite/analogAdenosine plays an important role in biochemical processes, such as energy transfer — as adenosine triphosphate (ATP) and adenosine diphosphate (ADP) — as well as in signal transduction as cyclic adenosine monophosphate, cAMP. It is also an inhibitory neurotransmitter, believed to play a role in promoting sleep and suppressing arousal. Adenosine also plays a role in regulation of blood flow to various organs through vasodilation.Adenosine is an endogenous purine nucleoside that modulates many physiological processes. Cellular signaling by adenosine occurs through four known adenosine receptor subtypes. Extracellular adenosine concentrations from normal cells are approximately 300 nM; however, in response to cellular damage (e.g. in inflammatory or ischemic tissue), these concentrations are quickly elevated (600–1,200 nM). Thus, in regard to stress or injury, the function of adenosine is primarily that of cytoprotection preventing tissue damage during instances of hypoxia, ischemia, and seizure activity. Activation of A2A receptors produces a constellation of responses that in general can be classified as anti-inflammatory.

 Names

Name adenosine
Synonym More Synonyms

 Adenosine Biological Activity

Description Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond.Target: Nucleoside antimetabolite/analogAdenosine plays an important role in biochemical processes, such as energy transfer — as adenosine triphosphate (ATP) and adenosine diphosphate (ADP) — as well as in signal transduction as cyclic adenosine monophosphate, cAMP. It is also an inhibitory neurotransmitter, believed to play a role in promoting sleep and suppressing arousal. Adenosine also plays a role in regulation of blood flow to various organs through vasodilation.Adenosine is an endogenous purine nucleoside that modulates many physiological processes. Cellular signaling by adenosine occurs through four known adenosine receptor subtypes. Extracellular adenosine concentrations from normal cells are approximately 300 nM; however, in response to cellular damage (e.g. in inflammatory or ischemic tissue), these concentrations are quickly elevated (600–1,200 nM). Thus, in regard to stress or injury, the function of adenosine is primarily that of cytoprotection preventing tissue damage during instances of hypoxia, ischemia, and seizure activity. Activation of A2A receptors produces a constellation of responses that in general can be classified as anti-inflammatory.
Related Catalog
Target

Human Endogenous Metabolite

References

[1]. Sato A, et al. Mechanism of vasodilation to adenosine in coronary arterioles from patients with heart disease. Am J Physiol Heart Circ Physiol. 2005 Apr;288(4):H1633-40.

[2]. Costa F, et al. Role of nitric oxide in adenosine-induced vasodilation in humans. Hypertension. 1998 May;31(5):1061-4.

 Chemical & Physical Properties

Density 2.1±0.1 g/cm3
Boiling Point 676.3±65.0 °C at 760 mmHg
Melting Point 234-236ºC
Molecular Formula C10H13N5O4
Molecular Weight 267.241
Flash Point 362.8±34.3 °C
Exact Mass 267.096741
PSA 139.54000
LogP -1.02
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.907
Stability Stable. Incompatible with strong oxidizing agents.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU7175000
CHEMICAL NAME :
Adenosine
CAS REGISTRY NUMBER :
58-61-7
LAST UPDATED :
199701
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C10-H13-N5-O4
MOLECULAR WEIGHT :
267.28
WISWESSER LINE NOTATION :
T56 BN DN FN HNJ IZ D- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
240 ug/kg
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
143 ug/kg/I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - headache
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
50 ug/kg/1M-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - bronchiolar constriction
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
360 ug/kg/1H-I
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Cardiac - change in rate
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
257 ug/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
171 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - coma Cardiac - pulse rate
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
257 ug/kg/1D-I
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction) Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>20 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Mammal - species unspecified Lymphocyte
DOSE/DURATION :
60 mmol/L
REFERENCE :
PNASA6 Proceedings of the National Academy of Sciences of the United States of America. (National Academy of Sciences, Printing & Pub. Office, 2101 Constitution Ave., Washington, DC 20418) V.1- 1915- Volume(issue)/page/year: 48,686,1962 *** REVIEWS *** TOXICOLOGY REVIEW ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 7,24,1957 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3937 No. of Facilities: 77 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 556 (estimated) No. of Female Employees: 387 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS AU7175000
HS Code 2934999090

 Synthetic Route

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Adenosin
β-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-
9β-D-ribofuranosyl-9H-Purin-6-amine
Adesine
1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-Ribofuranose
6-Amino-9-b-D-ribofuranosyl-9H-purine
Adenocor
Sandesin
(2R,3R,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol
9-β-δ-Ribofuranosidoadenine
(-)-adenosine
9-β-δ-Ribofuranosyl-9H-purin-6-amine
(–)-adenosine
9-b-D-Ribofuranosidoadenine
D-Adenosine
MFCD00005752
Adenosine
Adenine-9-beta-D-ribofuranoside
Adrekar
9-β-D-Ribofuranosyladenine
9-beta-D-Ribofuranosyladenine
9-b-D-Ribofuranosyl-9H-purin-6-amine
Boniton
Adenine riboside
Adenoscan
adenine-9β-D-Ribofuranoside
Adenocard
EINECS 200-389-9
9-β-D-Arabinofuranosyladenine
Myocol
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