Product Name

  • Name

    L(-)-Epinephrine

  • EINECS 200-098-7
  • CAS No. 51-43-4
  • Article Data23
  • CAS DataBase
  • Density 1.283 g/cm3
  • Solubility <0.01 g/100 mL at 18 °C
  • Melting Point 215 °C (dec.)(lit.)
  • Formula C9H13NO3
  • Boiling Point 413.1 °C at 760 mmHg
  • Molecular Weight 183.207
  • Flash Point 207.9 °C
  • Transport Information UN 2811 6.1/PG 2
  • Appearance off-white powder
  • Safety 36/37/39-45-61-26-23
  • Risk Codes 23/24/25-52/53-36/37/38-33
  • Molecular Structure Molecular Structure of 51-43-4 (L(-)-Epinephrine)
  • Hazard Symbols ToxicT
  • 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;
  • PSA 72.72000
  • LogP 0.74150

Synthetic route

(R)-4-(1-hydroxy-2-(methylamino)ethyl)benzen-1,2-diol L-tartrate

(R)-4-(1-hydroxy-2-(methylamino)ethyl)benzen-1,2-diol L-tartrate

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With ammonium hydroxide In water at 5 - 10℃; for 0.5h; pH=8.5;100%
(R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol
41787-64-8

(R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With boron tribromide97%
epinephrine bitartrate

epinephrine bitartrate

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With ammonium hydroxide In water at 5 - 15℃; for 3h; pH=9; Inert atmosphere; Darkness;93%
C38H43NO9

C38H43NO9

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 40℃; for 4h;89.7%
(R)-1-(3,4-bis(benzyloxy)phenyl)-2-(methylamino)ethan-1-ol hydrochloride

(R)-1-(3,4-bis(benzyloxy)phenyl)-2-(methylamino)ethan-1-ol hydrochloride

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium formate In methanol at 50℃;86%
benzyl (R)-(2-(3,4-bis(benzyloxy)phenyl)-2-hydroxyethyl)(methyl)carbamate

benzyl (R)-(2-(3,4-bis(benzyloxy)phenyl)-2-hydroxyethyl)(methyl)carbamate

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With formic acid; palladium 10% on activated carbon In methanol at 50℃; for 2h;81%
benzyl (R)-(2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)(methyl)carbamate

benzyl (R)-(2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)(methyl)carbamate

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With formic acid; palladium 10% on activated carbon In methanol at 50℃; for 1h;74%
R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-methylamido-ethan
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

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 6h; Ambient temperature;53.7%
adrenalone
99-45-6

adrenalone

A

C18H24N2O6

C18H24N2O6

B

L-epinephrine
51-43-4

L-epinephrine

C

(S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol
150-05-0

(S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol

Conditions
ConditionsYield
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
...Expand
dl-adrenaline

dl-adrenaline

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With D-tartaric acid
L-Tartaric acid
87-69-4

L-Tartaric acid

adrenalone
99-45-6

adrenalone

A

L-epinephrine
51-43-4

L-epinephrine

B

acid d-tartrate of d-adrenaline

acid d-tartrate of d-adrenaline

Conditions
ConditionsYield
With water; hydrogen; platinum aus der methylalkoholischen Loesung des Reaktionsprodukts scheidet sich das saure d-Tartrat des l-Adrenalins zuerst aus;
...Expand
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

hexadecyl magnesium iodide

hexadecyl magnesium iodide

A

L-epinephrine
51-43-4

L-epinephrine

B

potassium iodate

potassium iodate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) (-)-2-(2-HO-3-Br-5-t-Bu-C6H2-CH=N)-2'-HO-1,1'-binaphthyl, Ti(O-iPr)4, 2-HO-3,5-t-Bu2-C6H2-COOH, 2.) Me3SiCl, Et3N, 4.) TFA / 1.) toluene, 23 deg C, 1 h and 1 h, 23 deg C, 2.) toluene, -20 deg C, 15 min, 3.) toluene, -20 deg C to 23 deg C, 6 h, 4.) THF
2: imidazole / dimethylformamide
3: NaOH / H2O; methanol
4: SOCl2
5: NH4OH
6: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating
7: 97 percent / BBr3
View Scheme
...Expand
(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionamide

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionamide

A

L-epinephrine
51-43-4

L-epinephrine

B

potassium iodate

potassium iodate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating
2: 97 percent / BBr3
View Scheme
(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionic acid
188415-29-4

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionic acid

A

L-epinephrine
51-43-4

L-epinephrine

B

potassium iodate

potassium iodate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: SOCl2
2: NH4OH
3: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating
4: 97 percent / BBr3
View Scheme
(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionyl chloride

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionyl chloride

A

L-epinephrine
51-43-4

L-epinephrine

B

potassium iodate

potassium iodate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NH4OH
2: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating
3: 97 percent / BBr3
View Scheme
(S)-3-(3,4-Dimethoxy-phenyl)-3-hydroxy-propionic acid benzyl ester
188415-28-3

(S)-3-(3,4-Dimethoxy-phenyl)-3-hydroxy-propionic acid benzyl ester

A

L-epinephrine
51-43-4

L-epinephrine

B

potassium iodate

potassium iodate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: imidazole / dimethylformamide
2: NaOH / H2O; methanol
3: SOCl2
4: NH4OH
5: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating
6: 97 percent / BBr3
View Scheme
(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionic acid benzyl ester

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionic acid benzyl ester

A

L-epinephrine
51-43-4

L-epinephrine

B

potassium iodate

potassium iodate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: NaOH / H2O; methanol
2: SOCl2
3: NH4OH
4: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating
5: 97 percent / BBr3
View Scheme
1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamino-ethan-hydrochlorid
62-13-5

1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamino-ethan-hydrochlorid

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / NaHCO3 / benzene; H2O / 30 h
2: NaBH4 / methanol / 24 h
3: 53.7 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; palladium(II) hydroxide / water; methanol / 16 h / 10 - 40 °C / 150.01 Torr
2: methanol / 20 h / 20 °C / Large scale
3: ammonium hydroxide / water / 3 h / 5 - 15 °C / pH 9 / Inert atmosphere; Darkness
View Scheme
R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamido-ethan
104819-56-9, 104873-29-2, 104874-56-8

R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamido-ethan

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4 / methanol / 24 h
2: 53.7 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature
View Scheme
L-Tartaric acid
87-69-4

L-Tartaric acid

Epinephrine
329-65-7

Epinephrine

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Stage #1: L-Tartaric acid; Epinephrine at 20℃; for 1 - 3h;
Stage #2: With ammonia; sodium hydrogensulfite In water at 5 - 10℃; for 0.25h; pH=8.5; Product distribution / selectivity;
adrenalone
99-45-6

adrenalone

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With (R)-epinephrine dehydrogenase; NADH In aq. phosphate buffer at 45℃; pH=6; Kinetics; Reagent/catalyst; pH-value; Temperature; Enzymatic reaction; enantioselective reaction;n/a
2-chloro-3',4'-dihydroxyacetophenone
99-40-1

2-chloro-3',4'-dihydroxyacetophenone

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetonitrile; water / 3 h / 0 - 40 °C / Large scale
1.2: 1.5 h / 5 - 25 °C / Large scale
2.1: hydrogen; palladium(II) hydroxide / water; methanol / 16 h / 10 - 40 °C / 150.01 Torr
3.1: methanol / 20 h / 20 °C / Large scale
4.1: ammonium hydroxide / water / 3 h / 5 - 15 °C / pH 9 / Inert atmosphere; Darkness
View Scheme
norepinephrine
51-41-2

norepinephrine

S-Adenosyl-L-methionine
14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6

S-Adenosyl-L-methionine

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
With N-methyltransferase; 2-Amino-1-phenylethanol Enzymatic reaction;
L-tyrosine
60-18-4

L-tyrosine

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrobiopterin; oxygen; tyrosine hydroxylase / Enzymatic reaction
2: aromatic L-amino acid decarboxylase / Enzymatic reaction
3: oxygen; dopamine β-hydroxylase; ascorbic acid / Enzymatic reaction
4: 2-Amino-1-phenylethanol; N-methyltransferase / Enzymatic reaction
View Scheme
levodopa
59-92-7

levodopa

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aromatic L-amino acid decarboxylase / Enzymatic reaction
2: oxygen; dopamine β-hydroxylase; ascorbic acid / Enzymatic reaction
3: 2-Amino-1-phenylethanol; N-methyltransferase / Enzymatic reaction
View Scheme
benzene-1,2-diol
120-80-9

benzene-1,2-diol

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate / tetrahydrofuran; water / 5 h / 20 °C
2: trichlorophosphate / 3.5 h / 60 °C
3: water; ethanol / 2 h / 60 °C
4: sodium tetrahydroborate / ethanol / 5 h / 20 °C
5: hydrogenchloride / water; ethanol / 4 h / 40 °C
View Scheme
C35H36O8

C35H36O8

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trichlorophosphate / 3.5 h / 60 °C
2: water; ethanol / 2 h / 60 °C
3: sodium tetrahydroborate / ethanol / 5 h / 20 °C
4: hydrogenchloride / water; ethanol / 4 h / 40 °C
View Scheme
C37H37ClO9

C37H37ClO9

L-epinephrine
51-43-4

L-epinephrine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water; ethanol / 2 h / 60 °C
2: sodium tetrahydroborate / ethanol / 5 h / 20 °C
3: hydrogenchloride / water; ethanol / 4 h / 40 °C
View Scheme
Epinephrine
329-65-7

Epinephrine

A

L-epinephrine
51-43-4

L-epinephrine

B

(S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol
150-05-0

(S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol

Conditions
ConditionsYield
With core-shell macrocyclic glycopeptide-based chiral stationary phase NicoShell In methanol; acetic acid; acetonitrile at 20℃; Reagent/catalyst; Resolution of racemate;
With phase-transitioned bovine serum albumin film-coated capillary column In methanol pH=8.5; Resolution of racemate;
L-epinephrine
51-43-4

L-epinephrine

N-allyl isothiocyanate
57-06-7

N-allyl isothiocyanate

3-allyl-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-allyl-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h;85%
L-epinephrine
51-43-4

L-epinephrine

4-Chlorophenyl isothiocyanate
2131-55-7

4-Chlorophenyl isothiocyanate

3-(4-chlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-(4-chlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h;84%
L-epinephrine
51-43-4

L-epinephrine

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methyl-3-phenylthiourea

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methyl-3-phenylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 4h;82%
diethyl (α-acetoxymethyl)vinylphosphonate
1235976-42-7

diethyl (α-acetoxymethyl)vinylphosphonate

L-epinephrine
51-43-4

L-epinephrine

(R)-diethyl 3-((2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)methylamino)prop-1-en-2-ylphosphonate
1235976-71-2

(R)-diethyl 3-((2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)methylamino)prop-1-en-2-ylphosphonate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 20℃; for 24h;81%
3-bromophenyl isothiocyanate
2131-59-1

3-bromophenyl isothiocyanate

L-epinephrine
51-43-4

L-epinephrine

3-(3-bromophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-(3-bromophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h;81%
L-epinephrine
51-43-4

L-epinephrine

1-isothiocyanato-3-trifluoromethyl-benzene
1840-19-3

1-isothiocyanato-3-trifluoromethyl-benzene

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methyl-3-[3-(trifluoromethyl)phenyl]thiourea

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methyl-3-[3-(trifluoromethyl)phenyl]thiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h;80%
L-epinephrine
51-43-4

L-epinephrine

4-fluorophenyl isothiocyanate
1544-68-9

4-fluorophenyl isothiocyanate

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-3-(4-fluorophenyl)-1-methylthiourea

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-3-(4-fluorophenyl)-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h;79%
L-epinephrine
51-43-4

L-epinephrine

3,4-dichlorophenyl isothiocyanate
6590-94-9

3,4-dichlorophenyl isothiocyanate

3-(3,4-dichlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-(3,4-dichlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 4h;76%
L-epinephrine
51-43-4

L-epinephrine

germanium dioxide

germanium dioxide

C18H22GeN2O6

C18H22GeN2O6

Conditions
ConditionsYield
In water for 8h;76%
L-epinephrine
51-43-4

L-epinephrine

p-nitrophenyl isothiocyanate
2131-61-5

p-nitrophenyl isothiocyanate

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methyl-3-(4-nitrophenyl)thiourea

1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methyl-3-(4-nitrophenyl)thiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h;75%
L-epinephrine
51-43-4

L-epinephrine

3-chlorophenyl-isothiocyanate
2392-68-9

3-chlorophenyl-isothiocyanate

3-(3-chlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-(3-chlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 2.5h;74%
L-epinephrine
51-43-4

L-epinephrine

2, 4-dichlorophenyl isothiocyanate
6590-96-1

2, 4-dichlorophenyl isothiocyanate

3-(2,4-dichlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-(2,4-dichlorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h;73%
L-epinephrine
51-43-4

L-epinephrine

3-chloro-4-fluorophenyl isothiocyanate
137724-66-4

3-chloro-4-fluorophenyl isothiocyanate

3-(3-chloro-4-fluorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-(3-chloro-4-fluorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 2.5h;72%
2,6-difluorophenylisothiocyanate
207974-17-2

2,6-difluorophenylisothiocyanate

L-epinephrine
51-43-4

L-epinephrine

3-(2,6-difluorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

3-(2,6-difluorophenyl)-1-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-1-methylthiourea

Conditions
ConditionsYield
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h;71%
(R)-4-methyl-3-(3'-oxobutyl)pent-4-enal
7086-79-5, 85031-77-2, 127288-10-2, 136521-14-7

(R)-4-methyl-3-(3'-oxobutyl)pent-4-enal

L-epinephrine
51-43-4

L-epinephrine

(5R)-5-(2-{[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethyl](methyl)amino}ethyl)-6-methylhept-6-en-2-one

(5R)-5-(2-{[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethyl](methyl)amino}ethyl)-6-methylhept-6-en-2-one

Conditions
ConditionsYield
With trimethylamine-N-oxide; C27H28FeN3O3(1+)*BF4(1-); hydrogen In ethanol at 20℃; under 3750.38 Torr; for 16h; Autoclave; Inert atmosphere; chemoselective reaction;65%
formaldehyd
50-00-0

formaldehyd

L-epinephrine
51-43-4

L-epinephrine

1,2,3,4-tetrahydro-2-methyl-4,6,7-isoquinolinetriol hydrochloride
79254-32-3

1,2,3,4-tetrahydro-2-methyl-4,6,7-isoquinolinetriol hydrochloride

Conditions
ConditionsYield
In hydrogenchloride; water for 18h; Ambient temperature;57%
With hydrogenchloride; sodium hydrogencarbonate In water at 20℃; for 18h;49%
3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-propanoic acid,4-nitrophenyl ester

3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-propanoic acid,4-nitrophenyl ester

L-epinephrine
51-43-4

L-epinephrine

3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-N-methylpropanamide

3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-N-methylpropanamide

Conditions
ConditionsYield
In dimethyl sulfoxide; acetone48%
L-epinephrine
51-43-4

L-epinephrine

carbonic acid-p-(bis-2-chloroethylamino)phenyl ester-p-nitrophenyl ester

carbonic acid-p-(bis-2-chloroethylamino)phenyl ester-p-nitrophenyl ester

(R)-[1'-amino-2'-hydroxy-2'-(4''-hydroxyphenyl)propionic acid methyl ester]-carbamic acid p-(bis-2-chloroethylamino)phenyl ester
371754-23-3

(R)-[1'-amino-2'-hydroxy-2'-(4''-hydroxyphenyl)propionic acid methyl ester]-carbamic acid p-(bis-2-chloroethylamino)phenyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 72h;44%
formaldehyd
50-00-0

formaldehyd

L-epinephrine
51-43-4

L-epinephrine

A

1,2,3,4-tetrahydro-2-methyl-4,6,7-isoquinolinetriol hydrochloride
79254-32-3

1,2,3,4-tetrahydro-2-methyl-4,6,7-isoquinolinetriol hydrochloride

B

1,2,3,4-tetrahydro-2-methyl-4,7,8-isoquinolinetriol hydrochloride
79201-22-2

1,2,3,4-tetrahydro-2-methyl-4,7,8-isoquinolinetriol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogencarbonate In water for 1h;A n/a
B 22%
...Expand
(+/-)-9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid
51146-89-5

(+/-)-9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid

L-epinephrine
51-43-4

L-epinephrine

A

C27H41NO8
1100699-12-4

C27H41NO8

B

C27H41NO8
1100699-16-8

C27H41NO8

Conditions
ConditionsYield
With oxygen; tris hydrochloride In water; dimethyl sulfoxide at 25℃; for 15h; pH=8.0;A 18%
B 8%
With oxygen In water at 25℃; for 15h; pH=8;
...Expand
copper(II) nitrate pentahydrate

copper(II) nitrate pentahydrate

L-epinephrine
51-43-4

L-epinephrine

Cu(2+)*C6H3(OH)2CHOHCH2NHCH3*2NO3(1-)=[Cu(C6H3(OH)2CHOHCH2NHCH3)](NO3)2

Cu(2+)*C6H3(OH)2CHOHCH2NHCH3*2NO3(1-)=[Cu(C6H3(OH)2CHOHCH2NHCH3)](NO3)2

Conditions
ConditionsYield
In ethanol addn. of a soln. of metal salt in ethanol to a soln. of adrenaline in ethanol at 50°C with stirring; washing with ethanol, drying in vac.; elem. anal.;15%
L-epinephrine
51-43-4

L-epinephrine

1,13-bischloro-4,7,10-trioxatridecane
24997-19-1

1,13-bischloro-4,7,10-trioxatridecane

C34H50N2O10
125558-93-2

C34H50N2O10

Conditions
ConditionsYield
With sodium methylate In methanol; butan-1-ol for 20h; Heating;5%

L(-)-Epinephrine Chemical Properties

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

L(-)-Epinephrine 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.

L(-)-Epinephrine 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.

L(-)-Epinephrine 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.

L(-)-Epinephrine 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: ToxicT
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

L(-)-Epinephrine 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.

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