Product Name

  • Name

    DL-Adrenalin

  • EINECS 206-347-6
  • CAS No. 329-65-7
  • Article Data33
  • CAS DataBase
  • Density 1.283 g/cm3
  • Solubility slightly water soluble
  • Melting Point 197 °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
  • Appearance odorless light brown or nearly white crystals
  • Safety 26-36/37-45
  • Risk Codes 24-36/37/38
  • Molecular Structure Molecular Structure of 329-65-7 (DL-Adrenalin)
  • Hazard Symbols ToxicT
  • Synonyms 1,2-Benzenediol,4-[1-hydroxy-2-(methylamino)ethyl]-, (?à)-;Benzyl alcohol, 3,4-dihydroxy-a-[(methylamino)methyl]-, (?à)- (8CI);(?à)-Adrenaline;(?à)-Epinephrine;1-(3,4-Dihydroxy)phenyl-2-methylaminoethanol;2-(Methylamino)-1-(3,4-dihydroxyphenyl)ethanol;DL-Adrenaline;Epirenamine;Racepinefrine;Racepinephrine;dl-Adrenaline;
  • PSA 72.72000
  • LogP 0.74150

Synthetic route

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

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

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With salicylaldehyde; acetic acid at 90℃; for 4h; Temperature; Reagent/catalyst;92.7%
With hydrogenchloride In water at 80℃; for 1h;91.5%
1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamino-ethan-hydrochlorid
62-13-5

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

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogen; palladium(II) hydroxide In methanol; water at 10 - 40℃; under 150.015 Torr; for 16h;64%
Multi-step reaction with 3 steps
1: 73 percent / NaHCO3 / benzene; H2O / 30 h
2: 71 percent / NaBH4 / methanol / 24 h
3: 54.6 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature
View Scheme
R,S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-methylamido-ethan
104819-58-1, 104873-32-7, 104873-33-8

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

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 6h; Ambient temperature;54.6%
2-(benzyl-methyl-amino)-1-(3,4-dihydroxy-phenyl)-ethanone
36467-25-1

2-(benzyl-methyl-amino)-1-(3,4-dihydroxy-phenyl)-ethanone

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
Stage #1: 2-(benzyl-methyl-amino)-1-(3,4-dihydroxy-phenyl)-ethanone With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; water at 40℃; for 30 - 35h; pH=1.0 - 2.4;
Stage #2: With ammonia In water at 10 - 15℃; pH=8.5;
With hydrogenchloride; palladium Hydrogenation;
adrenalone
99-45-6

adrenalone

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With sodium hydroxide; nickel Hydrogenation;
With water; palladium Hydrogenation;
With sodium hydroxide; nickel Hydrogenation;
With sodium amalgam; ethanol
benzene-1,2-diol
120-80-9

benzene-1,2-diol

N-methylaminoacetaldehyde diethyl acetal
20677-73-0

N-methylaminoacetaldehyde diethyl acetal

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogenchloride at 100℃; das Hydrochlorid entsteht im Rohr;
With hydrogenchloride at 100℃; das Hydrochlorid entsteht im Rohr;
(-)-epinephrine
51-43-4, 150-05-0, 329-65-7, 6912-68-1

(-)-epinephrine

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogenchloride at 30.1℃; Rate constant;
3-methyl-5-<3.4-methylenedioxy-phenyl>-oxazolidone-(2)

3-methyl-5-<3.4-methylenedioxy-phenyl>-oxazolidone-(2)

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogenchloride
dl-adrenaline

dl-adrenaline

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With D-tartaric acid dextrorotatory methylaminomethyl-<3.4-dioxy-phenyl>-carbinol;
synephrine tartrate
67-04-9, 136-37-8, 136-38-9, 2410-00-6, 3459-11-8, 7418-89-5, 13998-28-2, 16589-24-5, 21254-60-4, 41787-41-1

synephrine tartrate

sodium chloride

sodium chloride

oxygen

oxygen

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
mit UV-Licht.Irradiation;
...Expand
ω-methylamino-3.4-dioxy-acetophenone hydrochloride

ω-methylamino-3.4-dioxy-acetophenone hydrochloride

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With water; hydrogen; palladium dichloride durch elektrolytische Reduktion an einer Palladiumkathode;
R,S-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,S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamido-ethan

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / NaBH4 / methanol / 24 h
2: 54.6 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature
View Scheme
C9H12NO3
115780-42-2

C9H12NO3

A

Epinephrine
329-65-7

Epinephrine

B

adrenaline o-quinone
672-73-1, 162706-73-2

adrenaline o-quinone

Conditions
ConditionsYield
With tert-butoxy radical; acetic acid In acetonitrile Kinetics; Inert atmosphere;
C24H21NO5

C24H21NO5

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; for 45h; Reflux;
2-chloro-3',4'-dihydroxyacetophenone
99-40-1

2-chloro-3',4'-dihydroxyacetophenone

Epinephrine
329-65-7

Epinephrine

Conditions
ConditionsYield
Multi-step reaction with 2 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
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

A

Epinephrine
329-65-7

Epinephrine

B

S-(5'-adenosyl)-L-homocysteine
979-92-0

S-(5'-adenosyl)-L-homocysteine

Conditions
ConditionsYield
With human phenylethanolamine N-methyltransferase In dimethyl sulfoxide at 25 - 100℃; for 0.583333h; Catalytic behavior; Enzymatic reaction;
...Expand
Epinephrine
329-65-7

Epinephrine

6-Nitro-adrenalin
25696-27-9

6-Nitro-adrenalin

Conditions
ConditionsYield
With phosphate buffer pH 7.4; sodium nitrite Ambient temperature;100%
With hydrogenchloride; sodium nitrite
methanol
67-56-1

methanol

Epinephrine
329-65-7

Epinephrine

4-(1-methoxy-2-methylamino-ethyl)-pyrocatechol; hydrochloride
74571-90-7

4-(1-methoxy-2-methylamino-ethyl)-pyrocatechol; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;98%
Epinephrine
329-65-7

Epinephrine

O,O‐diethyl 2-iodoethoxymethylphosphonate

O,O‐diethyl 2-iodoethoxymethylphosphonate

diethyl (2-((2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)(methyl)amino)ethoxy)methylphosphonate

diethyl (2-((2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)(methyl)amino)ethoxy)methylphosphonate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 10 - 50℃; for 3h;86%
Epinephrine
329-65-7

Epinephrine

4-(1-mercapto-2-methylamino-ethyl)-benzene-1,2-diol

4-(1-mercapto-2-methylamino-ethyl)-benzene-1,2-diol

Conditions
ConditionsYield
With polymer supported thiol; trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h;81%
Epinephrine
329-65-7

Epinephrine

(+/-)-epinine β-sulfonate < (+/-)-N-methyl-2-(3,4-dihydroxyphenyl)ethylammonium-2-sulfonate >
26405-77-6

(+/-)-epinine β-sulfonate < (+/-)-N-methyl-2-(3,4-dihydroxyphenyl)ethylammonium-2-sulfonate >

Conditions
ConditionsYield
With sodium sulfite68.8%
Epinephrine
329-65-7

Epinephrine

5,6-dihydroxy-1-methylindole
4821-00-5

5,6-dihydroxy-1-methylindole

Conditions
ConditionsYield
With sodium hydrogencarbonate; tartaric acid; potassium hexacyanoferrate(III) In water for 0.0833333h;57%
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

Epinephrine
329-65-7

Epinephrine

5-nitro-2--pyridine

5-nitro-2--pyridine

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 100℃; for 1h;31%
phosphorimetric microdetermination;
formaldehyd
50-00-0

formaldehyd

Epinephrine
329-65-7

Epinephrine

1,2,3,4-tetrahydro-4,6,7-trihydroxy-2-methylisoquinoline
72812-48-7, 82563-75-5

1,2,3,4-tetrahydro-4,6,7-trihydroxy-2-methylisoquinoline

Conditions
ConditionsYield
In methanol for 1h; Ambient temperature;23.7%
Epinephrine
329-65-7

Epinephrine

3-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazol-5-yl)isoxazole
1446358-48-0

3-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazol-5-yl)isoxazole

4-(2-((5-fluoro-2-(1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidin-4-yl)(methyl)amino)-1-hydroxyethyl)benzene-1,2-diol

4-(2-((5-fluoro-2-(1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidin-4-yl)(methyl)amino)-1-hydroxyethyl)benzene-1,2-diol

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 90℃; for 2h;14%
formaldehyd
50-00-0

formaldehyd

Epinephrine
329-65-7

Epinephrine

A

1,2,3,4-tetrahydro-4,7,8-trihydroxy-2-methylisoquinoline
82334-24-5

1,2,3,4-tetrahydro-4,7,8-trihydroxy-2-methylisoquinoline

B

1,2,3,4-tetrahydro-4,6,7-trihydroxy-2-methylisoquinoline
72812-48-7, 82563-75-5

1,2,3,4-tetrahydro-4,6,7-trihydroxy-2-methylisoquinoline

Conditions
ConditionsYield
With hydrogenchloride; ascorbic acid In water for 1h; Ambient temperature; in Tris-HCl buffer, pH 7.0;A 8.1%
B n/a
In water Product distribution; in acetate buffer, or phosphate buffer, or Tris buffer, or glycine buffer, effect of pH from pH 3 to 10.5; solvent also alcohol;
...Expand
Epinephrine
329-65-7

Epinephrine

7-bromo-3-hydroxy-1-methyl-indoline-5,6-dione
5257-04-5

7-bromo-3-hydroxy-1-methyl-indoline-5,6-dione

Conditions
ConditionsYield
With water; bromine; sodium acetate; acetic acid
Epinephrine
329-65-7

Epinephrine

3,4-Dihydroxyphenylacetaldehyde
5707-55-1

3,4-Dihydroxyphenylacetaldehyde

Conditions
ConditionsYield
With phosphoric acid
Epinephrine
329-65-7

Epinephrine

5-methylaminomethyl-5H-dibenzo[a,d]cycloheptene-2,3,7,8-tetraol
481-90-3

5-methylaminomethyl-5H-dibenzo[a,d]cycloheptene-2,3,7,8-tetraol

Conditions
ConditionsYield
With hydrogenchloride
With hydrogen bromide
With sulfuric acid
Epinephrine
329-65-7

Epinephrine

4-(1-chloro-2-methylamino-ethyl)-pyrocatechol; hydrochloride
90415-84-2

4-(1-chloro-2-methylamino-ethyl)-pyrocatechol; hydrochloride

Conditions
ConditionsYield
With thionyl chloride
Epinephrine
329-65-7

Epinephrine

(+/-)-2-(acetyl-methyl-amino)-1-(3,4-diacetoxy-phenyl)-ethanol
27669-45-0

(+/-)-2-(acetyl-methyl-amino)-1-(3,4-diacetoxy-phenyl)-ethanol

Conditions
ConditionsYield
With acetyl chloride
Epinephrine
329-65-7

Epinephrine

3-hydroxy-7-iodo-1-methyl-2,3-dihydro-indole-5,6-dione
5257-03-4

3-hydroxy-7-iodo-1-methyl-2,3-dihydro-indole-5,6-dione

Conditions
ConditionsYield
With hydrogenchloride; potassium iodate; water
Epinephrine
329-65-7

Epinephrine

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

methyl-(3,4,α-trihydroxy-phenethyl)-carbamic acid ethyl ester

methyl-(3,4,α-trihydroxy-phenethyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
With water
Epinephrine
329-65-7

Epinephrine

acetic anhydride
108-24-7

acetic anhydride

N-(3,4-dihydroxy-trans-styryl)-N-methyl-acetamide
99855-33-1

N-(3,4-dihydroxy-trans-styryl)-N-methyl-acetamide

Conditions
ConditionsYield
With methanol
Epinephrine
329-65-7

Epinephrine

acetic anhydride
108-24-7

acetic anhydride

1-acetoxy-2-(acetyl-methyl-amino)-1-(3,4-diacetoxy-phenyl)-ethane
27675-64-5

1-acetoxy-2-(acetyl-methyl-amino)-1-(3,4-diacetoxy-phenyl)-ethane

Conditions
ConditionsYield
With pyridine
Epinephrine
329-65-7

Epinephrine

acetic anhydride
108-24-7

acetic anhydride

(+/-)-2-(acetyl-methyl-amino)-1-(3,4-diacetoxy-phenyl)-ethanol
27669-45-0

(+/-)-2-(acetyl-methyl-amino)-1-(3,4-diacetoxy-phenyl)-ethanol

Conditions
ConditionsYield
With sodium hydrogencarbonate
Epinephrine
329-65-7

Epinephrine

acetyl chloride
75-36-5

acetyl chloride

1,2-diacetoxy-4-(1-chloro-2-methylamino-ethyl)-benzene

1,2-diacetoxy-4-(1-chloro-2-methylamino-ethyl)-benzene

Conditions
ConditionsYield
With hydrogenchloride; acetic acid
Epinephrine
329-65-7

Epinephrine

acetyl chloride
75-36-5

acetyl chloride

(+/-)-2-(acetyl-methyl-amino)-1-(3,4-dihydroxy-phenyl)-ethanol
103565-58-8

(+/-)-2-(acetyl-methyl-amino)-1-(3,4-dihydroxy-phenyl)-ethanol

Conditions
ConditionsYield
With sodium hydroxide; chloroform
Epinephrine
329-65-7

Epinephrine

methyl iodide
74-88-4

methyl iodide

vanillin
121-33-5

vanillin

Conditions
ConditionsYield
With sodium hydroxide
2,2,3,3,3-pentafluoropropanoic anhydride
356-42-3

2,2,3,3,3-pentafluoropropanoic anhydride

Epinephrine
329-65-7

Epinephrine

2,2,3,3,3-Pentafluoro-propionic acid 1-[3,4-bis-(2,2,3,3,3-pentafluoro-propionyloxy)-phenyl]-2-[methyl-(2,2,3,3,3-pentafluoro-propionyl)-amino]-ethyl ester
1995-97-7

2,2,3,3,3-Pentafluoro-propionic acid 1-[3,4-bis-(2,2,3,3,3-pentafluoro-propionyloxy)-phenyl]-2-[methyl-(2,2,3,3,3-pentafluoro-propionyl)-amino]-ethyl ester

Conditions
ConditionsYield
at 60℃; for 0.25h;
With formic acid at 80℃; for 0.583333h;

DL-Adrenalin Chemical Properties

Molecular structure of DL-Adrenalin (CAS NO.329-65-7) is:

Product Name: DL-Adrenalin
CAS Registry Number: 329-65-7
IUPAC Name: 4-[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: 206-347-6
Melting Point: 197 °C (dec.)(lit.)
Storage temp. 2-8°C
Water Solubility Sparingly soluble
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
Product Categories: Standards - 13C & 2H for GC-Mass Spectrometry

DL-Adrenalin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 7800ug/kg (7.8mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 68, Pg. 501, 1948.
mouse LD50 intravenous 3400ug/kg (3.4mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: "INFLAMMATION, NECROSIS, OR SCARRING OF BLADDER"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 502, 1949.
mouse LDLo subcutaneous 12mg/kg (12mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 57, 1948.
rabbit LDLo intravenous 250ug/kg (0.25mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 57, 1948.
rat LD50 intravenous 70ug/kg (0.07mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 502, 1949.

DL-Adrenalin Safety Profile

Safty information about DL-Adrenalin (CAS NO.329-65-7) is:

Hazard Codes: ToxicT
Risk Statements: 24-36/37/38 
R24:Toxic in contact with skin. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37-45 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: DO2975000
HazardClass: 6.1(b)
PackingGroup: III

DL-Adrenalin Specification

 DL-Adrenalin , its cas register number is 329-65-7. It also can be called 1-(3,4-Dihydroxyphenyl)-2-(methylamino)ethanol ; (+/-)-Adrenaline ; (+/-)-Epinephrine ; 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (+/-) ; 4-(1-Hydroxy-2-methylaminoethyl)benzene-1,2-diol ; Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (+/-) .It is a odorless light brown or nearly white crystals and slightly water soluble .

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