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DL-Adrenalin

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Name

DL-Adrenalin

EINECS 206-347-6
CAS No. 329-65-7 Density 1.283 g/cm3
PSA 72.72000 LogP 0.74150
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;

Article Data 33

DL-Adrenalin Synthetic route

150-05-0

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

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%
62-13-5

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

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
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

329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 6h; Ambient temperature;54.6%
36467-25-1

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

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;
99-45-6

adrenalone

329-65-7

Epinephrine

Conditions
ConditionsYield
With sodium hydroxide; nickel Hydrogenation;
With water; palladium Hydrogenation;
With sodium hydroxide; nickel Hydrogenation;
With sodium amalgam; ethanol
120-80-9

benzene-1,2-diol

20677-73-0

N-methylaminoacetaldehyde diethyl acetal

329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogenchloride at 100℃; das Hydrochlorid entsteht im Rohr;
With hydrogenchloride at 100℃; das Hydrochlorid entsteht im Rohr;
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)

329-65-7

Epinephrine

Conditions
ConditionsYield
With hydrogenchloride
dl-adrenaline

dl-adrenaline

329-65-7

Epinephrine

Conditions
ConditionsYield
With D-tartaric acid dextrorotatory methylaminomethyl-<3.4-dioxy-phenyl>-carbinol;
Conditions
ConditionsYield
mit UV-Licht.Irradiation;

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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