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104-14-3

Basic Information
CAS No.: 104-14-3
Name: Octopamine
Article Data: 23
Molecular Structure:
Molecular Structure of 104-14-3 (Octopamine)
Formula: C8H11NO2
Molecular Weight: 153.181
Synonyms: Benzylalcohol, a-(aminomethyl)-p-hydroxy-(6CI,8CI);(RS)-Octopamine;1-(p-Hydroxyphenyl)-2-aminoethanol;2-Amino-1-(4-hydroxyphenyl)ethanol;4-Hydroxyphenethanolamine;4-[2-Amino-1-hydroxyethyl]phenol;DL-Octopamine;Norsynephrine;Racemicoctopamine;p-Hydroxyphenylethanolamine;a-(Aminomethyl)-p-hydroxybenzylalcohol;
EINECS: 203-179-5
Density: 1.249 g/cm3
Melting Point: 157-158 °C
Boiling Point: 360.727 °C at 760 mmHg
Flash Point: 171.962 °C
Appearance: White to off-white powder
Transport Information: UN 3249 6.1/PG 2
PSA: 66.48000
LogP: 1.08460
Synthetic route

C14H14N2O6S

104-14-3

octopamine

Conditions
ConditionsYield
With potassium carbonate; thiophenol In N,N-dimethyl-formamide at 20℃; for 72h;77%
121778-81-2

5-(4-methoxy-phenyl)-oxazolidin-2-one

104-14-3

octopamine

Conditions
ConditionsYield
With N,N-dimethyl acetamide; boron tribromide In dichloromethane63%

2-benzylamino-1-(4-hydroxy-phenyl)-ethanone; hydrochloride

104-14-3

octopamine

Conditions
ConditionsYield
With palladium on activated charcoal; ethanol Hydrogenation;
645-36-3

2,2-diethoxy-ethanamine

108-95-2

phenol

104-14-3

octopamine

Conditions
ConditionsYield
With hydrogenchloride at 100℃;
60-19-5

tyramine hydrochloride

104-14-3

octopamine

Conditions
ConditionsYield
With N-Ethylmaleimide; acetate buffer; rat plasma; fumaric acid disodium salt; copper(II) sulfate; ascorbic acid; dopamine β-hydroxylase In water 1.) 37 deg C, pH=5.0, 5 min; 2.) 37 deg C, 45 min;
With N-Ethylmaleimide; acetate buffer; rat plasma; fumaric acid disodium salt; copper(II) sulfate; ascorbic acid; dopamine β-hydroxylase In water at 37℃; for 0.833333h; effect of cupric sulfate, catalase concentration and rat sample size;
2491-38-5

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone

104-14-3

octopamine

Conditions
ConditionsYield
(i) hexamethylenetetramine, (ii) aq. HCl, (iii) NaBH4; Multistep reaction;
7647-01-0

hydrogenchloride

645-36-3

2,2-diethoxy-ethanamine

108-95-2

phenol

104-14-3

octopamine

Conditions
ConditionsYield
at 100℃;
at 100℃;
hydrochloride of ω-amino-4-oxy-acetophenone

hydrochloride of ω-amino-4-oxy-acetophenone

104-14-3

octopamine

Conditions
ConditionsYield
With palladium on activated charcoal; water; hydrogen
With ethanol; sodium
64-17-5

ethanol

77369-38-1

2-amino-1-(4-hydroxyphenyl)ethyl ketone

sodium

sodium

104-14-3

octopamine

2-amino-1-<4-hydroxy-phenyl>-ethanone-(1)-hydrochloride

2-amino-1-<4-hydroxy-phenyl>-ethanone-(1)-hydrochloride

104-14-3

octopamine

Conditions
ConditionsYield
With water; palladium; palladium dichloride Hydrogenation;
With hydrogenchloride; platinized palladium Hydrogenation;
With hydrogenchloride; nickel Hydrogenation;
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Specification

The Benzenemethanol, a-(aminomethyl)-4-hydroxy-, with the CAS registry number 104-14-3, is also known as 1-(4-Hydroxyphenyl)-2-aminoethanol. It belongs to the classification code of Adrenergic Agents; Adrenergic Agonists; Adrenergic Alpha-agonists; Cardiovascular Agents; Drug / Therapeutic Agent; Neurotransmitter Agents; Vasoconstrictor Agents. Its EINECS registry number is 203-179-5. This chemical's molecular formula is C8H11NO2 and molecular weight is 153.18. What's more, both its IUPAC name and systematic name are the same which is called 4-(2-Amino-1-hydroxyethyl)phenol. It should be stored in a cool, dry and well-ventilated place. This chemical is an endogenous biogenic amine that is closely related to norepinephrine, and has effects on the adrenergic and dopaminergic systems. It is also found naturally in numerous plants, including bitter orange.

Physical properties about Benzenemethanol, a-(aminomethyl)-4-hydroxy- are: (1)ACD/LogP: -0.593 ; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.61; (4)ACD/LogD (pH 7.4): -2.45; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 66.48 Å2; (13)Index of Refraction: 1.614; (14)Molar Refractivity: 42.757 cm3; (15)Molar Volume: 122.612 cm3; (16)Polarizability: 16.95×10-24cm3; (17)Surface Tension: 61.463 dyne/cm; (18)Density: 1.249 g/cm3; (19)Flash Point: 171.962 °C; (20)Enthalpy of Vaporization: 63.991 kJ/mol; (21)Boiling Point: 360.727 °C at 760 mmHg; (22) Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Benzenemethanol, a-(aminomethyl)-4-hydroxy-: this chemical can be prepared by 5-(4-methoxy-phenyl)-oxazolidin-2-one. This reaction needs reagent BBr3/N,N-dimethylacetoamide and solvent CH2Cl2. The yield is 63 %.

Benzenemethanol, a-(aminomethyl)-4-hydroxy- can be prepared by 5-(4-methoxy-phenyl)-oxazolidin-2-one.

Uses of Benzenemethanol, a-(aminomethyl)-4-hydroxy-: it is used to produce other chemicals. For example, it can produce C9H13NO2·ClH. The reaction occurs with reagent HCl and the reaction time is 15 min. The yield is 90 %.

Benzenemethanol, a-(aminomethyl)-4-hydroxy- can produce C9H13NO2·ClH.

You can still convert the following datas into molecular structure:
(1) SMILES: OC(c1ccc(O)cc1)CN
(2) InChI: InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2
(3) InChIKey: QHGUCRYDKWKLMG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intravenous 200mg/kg (200mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 101, Pg. 81, 1955.
mouse LD50 intracrebral 2100mg/kg (2100mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
mouse LD50 intraperitoneal 600mg/kg (600mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 341, 1952.
mouse LD50 intravenous 75mg/kg (75mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 341, 1952.
mouse LD50 oral 4200mg/kg (4200mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
mouse LD50 subcutaneous 2070mg/kg (2070mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
rat LD50 intraperitoneal 1350mg/kg (1350mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
rat LD50 oral 1240mg/kg (1240mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
rat LD50 subcutaneous 350mg/kg (350mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.