CAS 51-42-3|Epinephrine bitartrate

Introduction:Basic information about CAS 51-42-3|Epinephrine bitartrate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameEpinephrine bitartrate
CAS Number51-42-3Molecular Weight333.291
Density/Boiling Point413.1ºC at 760 mmHg
Molecular FormulaC13H19NO9Melting Point~155 °C (dec.)
MSDSChineseUSAFlash Point207.9ºC
Symbol
GHS06
Signal WordDanger

Names

Name(-)-Epinephrine (+)-bitartrate salt
SynonymMore Synonyms

Epinephrine bitartrate BiologicalActivity

DescriptionL-Epinephrine bitartrate is an α-adrenergic and β-adrenergic receptor agonist. L-Epinephrine is a hormone secreted by the medulla of the adrenal glands.
Related CatalogSignaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorResearch Areas >>Neurological Disease
In VivoA 25 microliter volume of a 1-% L-epinephrine borate solution applied on the cornea of one eye in 12 monkeys reduces blood flow through the iris and the ciliary body by 59% and 20%, respectively, compared to the untreated control eyes[1]. Epinephrine is a direct-acting sympathomimetic α-adrenergic and β-adrenergic agonist with cyclic adenosine monophosphate-mediated, complex, bidirectional pharmacologic effects on many target organs[2]. In young adult rats, endogenous release of epinephrine facilitates stable memory formation for temporally associated events. Epinephrine enhances memory in young adult rats, in part, by increasing blood glucose levels needed to modulate memory[3]. Epinephrine is the primary drug administered during cardiopulmonary resuscitation (CPR) to reverse cardiac arrest. Epinephrine increases arterial blood pressure and coronary perfusion during CPR via alpha-1-adrenoceptor agonist effects[4].
References

[1]. Alm A, et al. The effect of topical l-epinephrine on regional ocular blood flow in monkeys. Invest Ophthalmol Vis Sci. 1980 May;19(5):487-91.

[2]. Simons FE, et al. First-aid treatment of anaphylaxis to food: focus on epinephrine. J Allergy Clin Immunol. 2004 May;113(5):837-44.

[3]. Morris KA, et al. Epinephrine and glucose modulate training-related CREB phosphorylation in old rats: relationships to age-related memory impairments. Exp Gerontol. 2013 Feb;48(2):115-27.

[4]. Callaway CW, et al. Epinephrine for cardiac arrest. Curr Opin Cardiol. 2013 Jan;28(1):36-42.

Chemical & Physical Properties

Boiling Point413.1ºC at 760 mmHg
Melting Point~155 °C (dec.)
Molecular FormulaC13H19NO9
Molecular Weight333.291
Flash Point207.9ºC
Exact Mass333.105988
PSA187.78000
Index of Refraction-16.5 ° (C=2, H2O)
InChIKeyYLXIPWWIOISBDD-UHFFFAOYSA-N
SMILESCNCC(O)c1ccc(O)c(O)c1.O=C(O)C(O)C(O)C(=O)O
StabilityStable. Incompatible with bases, oxidizing agents, iron, iron salts, copper, copper alloys.
Water SolubilityH2O: soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DO3500000
CAS REGISTRY NUMBER :
51-42-3
LAST UPDATED :
199706
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C9-H13-N-O3.C4-H6-O6
MOLECULAR WEIGHT :
333.33
WISWESSER LINE NOTATION :
QR BQ DYQ1M1 &QVYQYQVQ -L -D

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
8300 ug/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 :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
82 ug/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 :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 mg/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 :
7800 ug/kg
TOXIC EFFECTS :
Cardiac - cardiomyopathy including infarction
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
11100 ug/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 :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1780 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Cardiac - other changes Gastrointestinal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
76 mg/kg/42D-I
TOXIC EFFECTS :
Cardiac - other changes Liver - other changes Biochemical - Metabolism (Intermediary) - lipids including transport
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2400 ug/kg
SEX/DURATION :
male 2 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Cells - not otherwise specified
DOSE/DURATION :
1 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 43,3514,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 82895 No. of Facilities: 14 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 504 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 82895 No. of Facilities: 34 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 1721 (estimated) No. of Female Employees: 1639 (estimated)

Safety Information

Symbol
GHS06
Signal WordDanger
Hazard StatementsH300
Precautionary StatementsMissing Phrase - N15.00950417
Personal Protective EquipmentEyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard CodesT+:Verytoxic;
Risk PhrasesR28;R36/37/38
Safety PhrasesS26-S28-S36/37-S45
RIDADRUN 2811 6.1/PG 1
WGK Germany3
RTECSDO3500000
Packaging GroupIII
Hazard Class6.1(b)

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Synonyms

L-Adrenaline D-hydrogentartrate
L-Epinephrine D-hydrogentartrate
(-)-Epinephrine (+)-bitartrate salt
EINECS 200-097-1
(2R,3R)-2,3-Dihydroxysuccinic acid - 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol (1:1)
MFCD00035077
(2R,3R)-2,3-Dihydroxysuccinic acid - 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-1,2-benzenediol (1:1)
(-)-Epinephrine (+)-bitartrate
(R)-4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol (R-(R*,R*))-2,3-Dihydroxybutanedioate (1:1) (Salt)
(2R,3R)-2,3-Dihydroxybutandisäure--4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzol-1,2-diol(1:1)
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol 2,3-dihydroxybutanedioate (salt)
L-(-)-Epinephrine-(+)-bitartrate
acide (2R,3R)-2,3-dihydroxybutanedioïque - 4-[(1R)-1-hydroxy-2-(méthylamino)éthyl]benzène-1,2-diol (1:1)
Epinephrine bitartrate
(-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl Alcohol (+)-Tartrate (1:1) Salt
(-)-Epinephrine bitartrate
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-, compd. with 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-1,2-benzenediol (1:1)
EPINEPHRINE HYDROGEN TARTRATE
Epinephrine tartrate
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol 2,3-dihydroxybutanedioate (1:1)
L-Epinephrine (Bitartrate)
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