Octopamine supplier | CasNO.104-14-3

Name
Octopamine
EINECS 203-179-5
CAS No. 104-14-3
Article Data23
CAS DataBase
Density 1.249 g/cm³
Solubility
Melting Point 157-158 °C
Formula C₈H₁₁NO₂
Boiling Point 360.727 °C at 760 mmHg
Molecular Weight 153.181
Flash Point 171.962 °C
Transport Information UN 3249 6.1/PG 2
Appearance White to off-white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 66.48000
LogP 1.08460

Synthetic route

: C14H14N2O6S

: 104-14-3
octopamine

Conditions

Conditions	Yield
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

Conditions	Yield
With N,N-dimethyl acetamide; boron tribromide In dichloromethane	63%

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

: 104-14-3
octopamine

Conditions

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

: 645-36-3
2,2-diethoxy-ethanamine

: 108-95-2
phenol

: 104-14-3
octopamine

Conditions

Conditions	Yield
With hydrogenchloride at 100℃;

: 60-19-5
tyramine hydrochloride

: 104-14-3
octopamine

Conditions

Conditions	Yield
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

Conditions	Yield
(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

Conditions	Yield
at 100℃;
at 100℃;

...Expand

hydrochloride of ω-amino-4-oxy-acetophenone: hydrochloride of ω-amino-4-oxy-acetophenone

: 104-14-3
octopamine

Conditions

Conditions	Yield
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

...Expand

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

: 104-14-3
octopamine

Conditions

Conditions	Yield
With water; palladium; palladium dichloride Hydrogenation;
With hydrogenchloride; platinized palladium Hydrogenation;
With hydrogenchloride; nickel Hydrogenation;

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

: 104-14-3
octopamine

Conditions

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

: 831171-99-4
N-[2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-butyramide

: 104-14-3
octopamine

Conditions

Conditions	Yield
With hydrogenchloride In methanol

: 831172-00-0
[2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

: 104-14-3
octopamine

Conditions

Conditions	Yield
With hydrogenchloride In methanol

: 126395-31-1
tert-butyl (2-hydroxy-2-(4-hydroxyphenyl)ethyl)carbamate

: 104-14-3
octopamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Burkholderia cepacia lipase on Celite(R); sucrose; Tris-HCl buffer / toluene; tetrahydrofuran / 142 h / 40 °C / pH 7.9 2: HCl / methanol View Scheme
Multi-step reaction with 3 steps 1: caesium carbonate / acetone 2: chloro-trimethyl-silane / methanol / Darkness 3: aq. buffer / pH 7.2 / UV-irradiation View Scheme

: 121778-75-4
N-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-ethylamine

: 104-14-3
octopamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / K2S2O8, CuSO4 / 50 - 70 °C 2: 63 percent / BBr3/N,N-dimethylacetoamide / CH2Cl2 View Scheme

: 123-08-0
4-hydroxy-benzaldehyde

: 104-14-3
octopamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 20 °C / Inert atmosphere 2: 10% Pd/C; hydrogen / methanol / 12 h / 20 °C View Scheme

: 1-(4-hydroxyphenyl)-2-nitroethanol

: 104-14-3
octopamine

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen In methanol at 20℃; for 12h;

: 51-67-2
tyrosamine

: 104-14-3
octopamine

Conditions

Conditions	Yield
With Tyr216Ala Tyramine β‑Monooxygenase; potassium chloride; oxygen; copper(II) sulfate; sodium L-ascorbate In aq. phosphate buffer; water at 35℃; Kinetics; Temperature; pH-value; Enzymatic reaction;

: C25H29BrN2O6

: 104-14-3
octopamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chloro-trimethyl-silane / methanol / Darkness 2: aq. buffer / pH 7.2 / UV-irradiation View Scheme

: tert-butyl (2-(4-((8-cyano-7-(methoxymethoxy)quinolin-2-yl)-methoxy)phenyl)-2-hydroxyethyl)carbamate

: 104-14-3
octopamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chloro-trimethyl-silane / methanol / Darkness 2: aq. buffer / pH 7.2 / UV-irradiation View Scheme

: C18H17BrN2O3

: 104-14-3
octopamine

Conditions

Conditions	Yield
In aq. buffer pH=7.2; Wavelength; UV-irradiation;

: 2-((4-(2-amino-1-hydroxyethyl)phenoxy)methyl)-7-hydroxy-quinoline-8-carbonitrile

: 104-14-3
octopamine

Conditions

Conditions	Yield
In aq. buffer pH=7.2; Wavelength; UV-irradiation;

: 104-14-3
octopamine

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: 941584-96-9
4-(1-Hydroxy-2-(2-nitrophenylsulfonamido)ethyl)phenyl 2-nitrobenzenesulfonate

Conditions

Conditions	Yield
Stage #1: octopamine With sodium hydroxide In 1,4-dioxane; water at 20℃; for 0.0833333h; Stage #2: 2-Nitrobenzenesulfonyl chloride In 1,4-dioxane; water at 20℃; for 17h;	97%
Stage #1: octopamine With sodium hydroxide In 1,4-dioxane; water at 20℃; for 0.0833333h; Stage #2: 2-Nitrobenzenesulfonyl chloride In 1,4-dioxane; water at 20℃; for 17h;	97%

: 104-14-3
octopamine

: 59908-54-2
<(5-methoxy-1-methyl)indol-2-yl>carboxylic acid

: 1048685-09-1
C19H20N2O4

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1,2-dichloro-ethane In tetrahydrofuran at 20℃;	96%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;

: 67-56-1
methanol

: 104-14-3
octopamine

: 74571-92-9
4-(2-Amino-1-methoxy-ethyl)-phenol; hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 0.25h;	90%

: 104-14-3
octopamine

: 380607-13-6
5,6-dimethoxy-1-methyl-1H-indole-2-carboxylic acid

: 1048685-05-7
C20H22N2O5

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1,2-dichloro-ethane In tetrahydrofuran at 20℃;	88%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;

: 104-14-3
octopamine

: C18H17NO4

: 1048685-13-7
C26H26N2O5

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1,2-dichloro-ethane In tetrahydrofuran at 20℃;	87%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;

: 104-14-3
octopamine

: 5068-28-0
(2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid

: C23H30N2O5S

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1,2-dichloro-ethane at 20℃; for 2h;	86%

: 104-14-3
octopamine

: 24424-99-5
di-tert-butyl dicarbonate

: 126395-31-1
tert-butyl (2-hydroxy-2-(4-hydroxyphenyl)ethyl)carbamate

Conditions

Conditions	Yield
In methanol at 20℃;	84%
With triethylamine In methanol

: 104-14-3
octopamine

: 24424-99-5
di-tert-butyl dicarbonate

: 1426855-37-9
(±)-tert-butyl 2-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxyethylcarbamate

Conditions

Conditions	Yield
Stage #1: octopamine With hydrogenchloride; bromine In water at 5 - 20℃; for 1h; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide at 20℃; for 0.5h;	80%

: 104-14-3
octopamine

: C28H29N3O3

: C36H38N4O4

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 0℃;	60%

: 104-14-3
octopamine

: C28H29N3O3

: C36H38N4O4

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 0℃;	60%

: 104-14-3
octopamine

: 121409-54-9
(2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)acetone

: 1-(4-Hydroxyphenyl)-2-[1-methyl-2-(2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) ethylamino]ethanol

Conditions

Conditions	Yield
	47%

: 104-14-3
octopamine

: 24463-15-8
1-pyrenemethanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1448344-25-9
N-[(pyren-1-yl)methoxycarbonyl]-2-(4'-hydroxy-1'-phenyl)-2-hydroxyethylamine

Conditions

Conditions	Yield
Stage #1: 1-pyrenemethanol; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: octopamine In N,N-dimethyl-formamide for 12h;	36%

...Expand

: 104-14-3
octopamine

: 373359-53-6
N-{4-[4-(4-oxopiperidin-1-yl)phenylsulfamoyl]phenyl}acetamide

: N-(4-{[4-(4-{[2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino}-1-piperidinyl)anilino]sulfonyl}phenyl)acetamide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 258.574 - 1034.3 Torr;	19%

: 104-14-3
octopamine

: 51-67-2
tyrosamine

Conditions

Conditions	Yield
With palladium on activated charcoal; acetic acid Hydrogenation;

: 104-14-3
octopamine

A: 2-benzoylamino-1-(4-benzoyloxy-phenyl)-ethanol

B: 1-(2-benzoylamino-1-benzoyloxy-ethyl)-4-benzoyloxy-benzene

Conditions

Conditions	Yield
durch Benzoylierung nach Schotten-Baumann;

: 104-14-3
octopamine

: 1-(2-benzoylamino-1-benzoyloxy-ethyl)-4-benzoyloxy-benzene

Conditions

Conditions	Yield
durch Benzoylierung;

: 104-14-3
octopamine

: 4-(2-Oxo-propoxy)-benzamide

: 36611-38-8
4-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-propoxy}-benzamide

Conditions

Conditions	Yield
(i) EtOH, (ii) H2, PtO2; Multistep reaction;

: 104-14-3
octopamine

: 5-Methyl-2-(2-oxo-propoxy)-benzamide

: 47453-84-9
2-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-propoxy}-5-methyl-benzamide

Conditions

Conditions	Yield
(i) EtOH, (ii) H2, PtO2; Multistep reaction;

: 104-14-3
octopamine

: 356-42-3
2,2,3,3,3-pentafluoropropanoic anhydride

: 62237-94-9
Octopamin-pentafluorpropionat

Conditions

Conditions	Yield
at 60℃; for 0.25h;

: 104-14-3
octopamine

: 99-96-7
4-hydroxy-benzoic acid

Conditions

Conditions	Yield
With sodium periodate at 20 - 30℃;

: 104-14-3
octopamine

: 54-47-7
pyridoxal 5'-phosphate

: Phosphoric acid mono-(5-hydroxy-4-{[(E)-2-hydroxy-2-(4-hydroxy-phenyl)-ethylimino]-methyl}-6-methyl-pyridin-3-ylmethyl) ester

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water for 10h; Heating;

: 104-14-3
octopamine

: 66-72-8
pyridoxal

: 4-{[(E)-2-Hydroxy-2-(4-hydroxy-phenyl)-ethylimino]-methyl}-5-hydroxymethyl-2-methyl-pyridin-3-ol

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water for 10h; Heating;

: 104-14-3
octopamine

: 102-92-1
Cinnamoyl chloride

: N-2-hydroxy-2-(4-hydroxyphenyl)ethyl cinnamide

Conditions

Conditions	Yield
In sodium hydroxide for 0.25h;

: 104-14-3
octopamine

: 826-01-7
(S)-1-hydroxy-1-(4-hydroxyphenyl)-2-aminoethane

: 104-14-3
octopamine

: 876-04-0
(R)-octopamine

Octopamine 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)	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.

Product Name

Octopamine

Synthetic route

Octopamine Specification

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