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| CAS No.: | 51-43-4 |
|---|---|
| Name: | L(-)-Epinephrine |
| Article Data: | 23 |
| Molecular Structure: | |
|
|
|
| Formula: | C9H13NO3 |
| Molecular Weight: | 183.207 |
| Synonyms: | 1,2-Benzenediol,4-[1-hydroxy-2-(methylamino)ethyl]-, (R)-;Benzyl alcohol, 3,4-dihydroxy-a-[(methylamino)methyl]-, (-)-(8CI);(-)-(R)-Epinephrine;(-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol;(-)-Adrenaline;(-)-Epinephrine;(R)-Adrenaline;(R)-Epinephrine;Adnephrine;Adrenal;Adrenalin;Adrenaline;Adrenine;Bronkaid Mist;Chelafrin;Epifrin;Epinefrina;Epinephran;Exadrin;Glauposine;Hemisine;Isoptoepinal;L-Adrenaline;Levoepinephrine;Levorenen;Levoreninum;Lyodrin;Methylarterenol;N-[(2R)-2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]-N-methylamine;NSC 62786;Paranephrin;R-(-)-Epinephrine;Renaglandin;Renalina;Renoform;Renostypticin;Scurenaline;Styptirenal;Supranephrane;Suprarenaline;Vasoconstrictine;Vasotonin;l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol;l-Epinephrine; |
| EINECS: | 200-098-7 |
| Density: | 1.283 g/cm3 |
| Melting Point: | 215 °C (dec.)(lit.) |
| Boiling Point: | 413.1 °C at 760 mmHg |
| Flash Point: | 207.9 °C |
| Solubility: | <0.01 g/100 mL at 18 °C |
| Appearance: | off-white powder |
| Hazard Symbols: |
 T
|
| Risk Codes: | 23/24/25-52/53-36/37/38-33 |
| Safety: | 36/37/39-45-61-26-23 |
| Transport Information: | UN 2811 6.1/PG 2 |
| PSA: | 72.72000 |
| LogP: | 0.74150 |
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- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With ammonium hydroxide In water at 5 - 10℃; for 0.5h; pH=8.5; | 100% |
- 41787-64-8
(R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With boron tribromide | 97% |
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With ammonium hydroxide In water at 5 - 15℃; for 3h; pH=9; Inert atmosphere; Darkness; | 93% |
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol; water at 40℃; for 4h; | 89.7% |
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With palladium 10% on activated carbon; ammonium formate In methanol at 50℃; | 86% |
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With formic acid; palladium 10% on activated carbon In methanol at 50℃; for 2h; | 81% |
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With formic acid; palladium 10% on activated carbon In methanol at 50℃; for 1h; | 74% |
- 104819-58-1, 104873-32-7, 104873-33-8
R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-methylamido-ethan
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 6h; Ambient temperature; | 53.7% |
| Conditions | Yield |
|---|---|
| With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide; isopropyl alcohol Electrochemical reaction; Title compound not separated from byproducts.; | A 5% B n/a C n/a |
- 51-43-4
L-epinephrine
| Conditions | Yield |
|---|---|
| With D-tartaric acid |
- Total:0 Page 0 of 0
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Chemistry
Molecular structure of Adrenaline (CAS NO.51-43-4) is:
IUPAC Name: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Molecular Weight: 183.20442 g/mol
Molecular Formula: C9H13NO3
XLogP3: -1.4
H-Bond Donor: 4
H-Bond Acceptor: 4
EINECS: 200-098-7
Melting Point: 215 °C (dec.)(lit.)
Surface Tension: 59.9 dyne/cm
Density: 1.283 g/cm3
Flash Point: 207.9 °C
Enthalpy of Vaporization: 70.21 kJ/mol
Boiling Point: 413.1 °C at 760 mmHg
Vapour Pressure: 1.45E-07 mmHg at 25 °C
Storage temp.: 2-8°C
Water Solubility: <0.01 g/100 mL at 18 °C
Sensitive: Air & Light Sensitive
Stability: Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. Light sensitive.
Product Categories: Medical Fabric;Standards - 13C & 2H for GC-Mass Spectrometry
Uses
Adrenaline (CAS NO.51-43-4) can be used in a variety of preparations for the management of several medical conditions. It is used as a drug to treat cardiac arrest and other cardiac dysrhythmias resulting in diminished or absent cardiac output.And it is the drug of choice for treating anaphylaxis. It is also useful in treating sepsis. It is available in an autoinjector delivery system.It has historically been used for the treatment of croup.
Production
Adrenaline (CAS NO.51-43-4) may be synthesized by the reaction of catechol with chloroacetyl chloride, followed by the reaction with methylamine to give the ketone, which is reduced to the desired hydroxy compound. .jpg)
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | intravenous | 500ug/kg (0.5mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| cat | LDLo | subcutaneous | 20mg/kg (20mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| dog | LD50 | intravenous | 100ug/kg (0.1mg/kg) | Drugs in Japan Vol. 6, Pg. 120, 1982. | |
| dog | LD50 | subcutaneous | 5mg/kg (5mg/kg) | Drugs in Japan Vol. 6, Pg. 120, 1982. | |
| dog | LDLo | parenteral | 5ug/kg (0.005mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 1, Pg. 189, 1968. |
| guinea pig | LDLo | intravenous | 100ug/kg (0.1mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| guinea pig | LDLo | subcutaneous | 800ug/kg (0.8mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| infant | TDLo | multiple routes | 625ug/kg/I (0.625mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: CYANOSIS KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Southern Medical Journal. Vol. 78, Pg. 874, 1985. |
| man | LDLo | subcutaneous | 7ug/kg (0.007mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES CARDIAC: OTHER CHANGES | Annals of Emergency Medicine. Vol. 28, Pg. 725, 1996. |
| man | TDLo | intramuscular | 2ug/kg (0.002mg/kg) | VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION | American Journal of Emergency Medicine. Vol. 8, Pg. 46, 1990. |
| man | TDLo | intravenous | 16ug/kg (0.016mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" CARDIAC: CHANGE IN RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | American Journal of Emergency Medicine. Vol. 5, Pg. 64, 1987. |
| man | TDLo | intravenous | 285ug/kg (0.285mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE | American Journal of Emergency Medicine. Vol. 7, Pg. 485, 1989. |
| man | TDLo | intravenous | 3mg/kg (3mg/kg) | VASCULAR: CONTRACTION (ISOLATED TISSUES) | American Journal of Emergency Medicine. Vol. 8, Pg. 46, 1990. |
| man | TDLo | oral | 77mg/kg (77mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: EXCITEMENT GASTROINTESTINAL: NAUSEA OR VOMITING | Annals of Emergency Medicine. Vol. 19, Pg. 671, 1990. |
| man | TDLo | subcutaneous | 8571ng/kg/80M (0.008571mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION | American Heart Journal. Vol. 111, Pg. 1193, 1986. |
| man | TDLo | subcutaneous | 43ug/kg (0.043mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Annals of Emergency Medicine. Vol. 19, Pg. 680, 1990. |
| mouse | LD50 | intraperitoneal | 4mg/kg (4mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 110, 1947. | |
| mouse | LD50 | intravenous | 217ug/kg (0.217mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976. |
| mouse | LD50 | subcutaneous | 1470ug/kg (1.47mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 202, Pg. 658, 1943. | |
| mouse | LDLo | oral | 50mg/kg (50mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| mouse | LDLo | unreported | 10mg/kg (10mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: EXCITEMENT | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 162, Pg. 46, 1931. |
| rabbit | LD50 | intravenous | 50ug/kg (0.05mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941. |
| rabbit | LD50 | subcutaneous | 4mg/kg (4mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941. |
| rabbit | LDLo | oral | 30mg/kg (30mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| rat | LD50 | intramuscular | 3500mg/kg (3500mg/kg) | "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 105, 1973. | |
| rat | LD50 | intravenous | 150ug/kg (0.15mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 41, Pg. 365, 1931. | |
| rat | LD50 | skin | 62mg/kg (62mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 8(4), Pg. 30, 1964. |
| rat | LD50 | subcutaneous | 5mg/kg (5mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941. |
| rat | LDLo | intraperitoneal | 10mg/kg (10mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 268, 1946. |
| rat | LDLo | oral | 30mg/kg (30mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| women | TDLo | intravenous | 6ug/kg (0.006mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | British Medical Journal. Vol. 286, Pg. 519, 1983. |
Safety Profile
Human poison by subcutaneous route. Experimental poison by ingestion, skin contact, subcutaneous, intraperitoneal, intravenous, and intramuscular routes. Human systemic effects: cardiomyopathy including infarction, arrhythmias. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
T
Risk Statements: 23/24/25-52/53-36/37/38-33
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R36/37/38:Irritating to eyes, respiratory system and skin.
R33:Danger of cumulative effects.
Safety Statements: 36/37/39-45-61-26-23
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S33:Take precautionary measures against static discharges.
RIDADR: UN 2811 6.1/PG 2
WGK Germany :3
RTECS: DO2625000
F: 8-10-23
HazardClass: 6.1
PackingGroup: II
Specification
Adrenaline , its cas register number is 51-43-4. It also can be called (-)-(R)-Epinephrine ; (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol ; (R)-Adrenaline ; (R)-Epinephrine ; 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)- ; 1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol ; 1-Adrenalin ; 1-Epinephrine ; 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol ; Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)- .It is a off-white powder.It is a is a hormone and neurotransmitter.