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Epinephrine bitartrate

Names

[ CAS No. ]:
51-42-3

[ Name ]:
Epinephrine bitartrate

[Synonym ]:
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)

Biological Activity

[Description]:

L-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 Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor
Research Areas >> Neurological Disease

[In Vivo]

A 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.


[Related Small Molecules]

Isoprenaline hydrochloride | ICI 118,551 (hydrochloride) | Phenylephrine hydrochloride | Yohimbine hydrochloride | Adrenaline | Ivabradine hydrochloride | Prazosin hydrochloride | Clenbuterol hydrochloride | Phentolamine mesilate | guanfacine hydrochloride | pimozide | Sotalol hydrochloride | Carvedilol | Atenolol | Metroprolol succinate

Chemical & Physical Properties

[ Boiling Point ]:
413.1ºC at 760 mmHg

[ Melting Point ]:
~155 °C (dec.)

[ Molecular Formula ]:
C13H19NO9

[ Molecular Weight ]:
333.291

[ Flash Point ]:
207.9ºC

[ Exact Mass ]:
333.105988

[ PSA ]:
187.78000

[ Index of Refraction ]:
-16.5 ° (C=2, H2O)

[ Stability ]:
Stable. Incompatible with bases, oxidizing agents, iron, iron salts, copper, copper alloys.

[ Water Solubility ]:
H2O: soluble

MSDS

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 Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
Missing Phrase - N15.00950417

[ Personal Protective Equipment ]:
Eyeshields;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 Codes ]:
T+:Verytoxic;

[ Risk Phrases ]:
R28;R36/37/38

[ Safety Phrases ]:
S26-S28-S36/37-S45

[ RIDADR ]:
UN 2811 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
DO3500000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

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