CAS 51-42-3|Epinephrine bitartrate
| Common Name | Epinephrine bitartrate | ||
|---|---|---|---|
| CAS Number | 51-42-3 | Molecular Weight | 333.291 |
| Density | / | Boiling Point | 413.1ºC at 760 mmHg |
| Molecular Formula | C13H19NO9 | Melting Point | ~155 °C (dec.) |
| MSDS | ChineseUSA | Flash Point | 207.9ºC |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | (-)-Epinephrine (+)-bitartrate salt |
|---|---|
| Synonym | More Synonyms |
Epinephrine bitartrate BiologicalActivity
| 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 ReceptorResearch 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. |
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) |
| InChIKey | YLXIPWWIOISBDD-UHFFFAOYSA-N |
| SMILES | CNCC(O)c1ccc(O)c(O)c1.O=C(O)C(O)C(O)C(=O)O |
| Stability | Stable. Incompatible with bases, oxidizing agents, iron, iron salts, copper, copper alloys. |
| Water Solubility | H2O: soluble |
Toxicological Information
CHEMICAL IDENTIFICATION |
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)
- 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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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) |
