Product Name

  • Name

    3-Hydroxytyramine

  • EINECS 200-110-0
  • CAS No. 51-61-6
  • Article Data59
  • CAS DataBase
  • Density 1.248 g/cm3
  • Solubility
  • Melting Point 218-220 oC
  • Formula C8H11NO2
  • Boiling Point 337.69 °C at 760 mmHg
  • Molecular Weight 153.181
  • Flash Point 158.03 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 51-61-6 (3-Hydroxytyramine)
  • Hazard Symbols
  • Synonyms Pyrocatechol,4-(2-aminoethyl)- (8CI);2-(3,4-Dihydroxyphenyl)-1-ethanamine;2-(3,4-Dihydroxyphenyl)ethylamine;3,4-Dihydroxyphenylethylamine;3-Hydroxytyramine;4-(2-Aminoethyl)-1,2-benzenediol;4-(2-Aminoethyl)catechol;Hydroxytyramin;NSC 173182;Oxytyramine;
  • PSA 66.48000
  • LogP 1.29930

Synthetic route

levodopa
59-92-7

levodopa

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h;82%
beim Erhitzen ueber den Schmelzpunkt;
With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate at 30℃; for 0.5h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;
3-Methoxytyramine
554-52-9

3-Methoxytyramine

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With oxygen; copper(II) perchlorate; ascorbic acid In water19%
With P4502D6 Kinetics; Enzymatic reaction;
3-amino-4-hydroxyphenylethylamine
81666-88-8

3-amino-4-hydroxyphenylethylamine

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With barium nitrite; sulfuric acid Diazotization.und Eingiessen der Loesung in siedende Kupfersulfat-Loesung;
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With hydrogenchloride at 170℃;
With hydrogen bromide at 130℃;
With hydrogenchloride at 150℃;

A

dopamine
51-61-6

dopamine

B

1,2,3,4-tetrahdyro-1-methylisopquinoline-7,8-diol
53405-13-3, 102917-28-2

1,2,3,4-tetrahdyro-1-methylisopquinoline-7,8-diol

Conditions
ConditionsYield
In water at 180℃; for 28h; Product distribution; var. time;
2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline
57894-18-5

2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With hydrazine
N-(tert-butoxycarbonyl)dopamine
37034-31-4

N-(tert-butoxycarbonyl)dopamine

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid
Multi-step reaction with 3 steps
1: caesium carbonate / acetone / 24 h / 20 °C
2: chloro-trimethyl-silane / methanol / 20 °C
3: aq. buffer / pH 7.2 / Irradiation
View Scheme
N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine
37034-22-3

N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
Norlaudanosolin
4747-99-3

Norlaudanosolin

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
In water at 180℃; for 66h; Mechanism; other tetraisoquinolines;
2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin
76734-99-1

2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin

A

dopamine
51-61-6

dopamine

B

arterenone
499-61-6

arterenone

C

2-hydroxy-3′,4′-dihydroxyacetophenone
29477-54-1

2-hydroxy-3′,4′-dihydroxyacetophenone

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 3h;
2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin
76734-99-1

2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin

A

dopamine
51-61-6

dopamine

B

2-hydroxy-3′,4′-dihydroxyacetophenone
29477-54-1

2-hydroxy-3′,4′-dihydroxyacetophenone

Conditions
ConditionsYield
With hydrogenchloride for 3h; Heating;
4-(N,N-dimethylamino)phenol
619-60-3

4-(N,N-dimethylamino)phenol

C8H10NO2

C8H10NO2

A

dopamine
51-61-6

dopamine

B

4-(N,N-dimethylamino)phenoxyl radical
54737-34-7

4-(N,N-dimethylamino)phenoxyl radical

Conditions
ConditionsYield
With potassium hydroxide In water Equilibrium constant; Irradiation;
dopaminoquinone
50673-96-6

dopaminoquinone

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
Rate constant; pH 7.00; reaction with substrate reduced glucose oxidase;
With citric acid In phosphate buffer pH=6.3;
With sulfuric acid In water at 22℃; pH=1; Electrolysis; Inert atmosphere;
α-amino-β-<3.4-dioxy-phenyl>-propionic acid

α-amino-β-<3.4-dioxy-phenyl>-propionic acid

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
ueber den Schmelzpunkt;
3.4-dihydroxy-DL-mandelonitrile

3.4-dihydroxy-DL-mandelonitrile

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With hydrogenchloride; platinum Hydrogenation;
carbonic-acid
463-79-6

carbonic-acid

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With hydrogen iodide
tyrosamine
51-67-2

tyrosamine

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

iron(II) sulfate

iron(II) sulfate

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
Reaktion des Hydrochlorids;
4-<2-amino-<1-14C>ethyl>-pyrocatechol

4-<2-amino-<1-14C>ethyl>-pyrocatechol

dopamine
51-61-6

dopamine

4-<2-amino-<1,1-3H2>ethyl>-pyrocatechol

4-<2-amino-<1,1-3H2>ethyl>-pyrocatechol

dopamine
51-61-6

dopamine

4-<2-amino-<2-14C>ethyl>-pyrocatechol

4-<2-amino-<2-14C>ethyl>-pyrocatechol

dopamine
51-61-6

dopamine

4-<2-amino-ethyl>-<3-14C>pyrocatechol

4-<2-amino-ethyl>-<3-14C>pyrocatechol

dopamine
51-61-6

dopamine

4-<2-amino-ethyl>-<4-14C>pyrocatechol

4-<2-amino-ethyl>-<4-14C>pyrocatechol

dopamine
51-61-6

dopamine

4-<2-amino-ethyl>-<5-14C>pyrocatechol

4-<2-amino-ethyl>-<5-14C>pyrocatechol

dopamine
51-61-6

dopamine

tyramine hydrochloride

tyramine hydrochloride

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
With dihydrogen peroxide; iron(II) sulfate
sulfuric acid
7664-93-9

sulfuric acid

3-amino-4-hydroxyphenylethylamine
81666-88-8

3-amino-4-hydroxyphenylethylamine

barium nitrite

barium nitrite

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
und Eintragen der Diazoloesung in siedende konzentrierte Kupfersulfat-Loesung;
tyrosamine
51-67-2

tyrosamine

A

dopamine
51-61-6

dopamine

B

dopaminoquinone
50673-96-6

dopaminoquinone

Conditions
ConditionsYield
With tyrosinase In phosphate buffer for 0.333333h; pH=6.3;
N-[2-(3-methoxy-4-hydroxy-phenyl)ethyl]phthalimide
37627-79-5

N-[2-(3-methoxy-4-hydroxy-phenyl)ethyl]phthalimide

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 14 percent / oxygen, cupric perchlorate, ascorbic acid / H2O; acetone / 24 h / 60 °C
2: NH2NH2
View Scheme
tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate
23699-77-6

tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate

dopamine
51-61-6

dopamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 28 percent / oxygen, cupric perchlorate, ascorbic acid, monosodium ascorbate / H2O; acetone / 27 h / 20 °C
2: TFA, PhOMe
View Scheme
dopamine
51-61-6

dopamine

4-(2-aminoethyl)-5-nitrobenzene-1,2-diol
21581-49-7

4-(2-aminoethyl)-5-nitrobenzene-1,2-diol

Conditions
ConditionsYield
With phosphate buffer pH 7.4; sodium nitrite Ambient temperature;100%
dopamine
51-61-6

dopamine

4-hydroxyphenylacetaldehyde
7339-87-9

4-hydroxyphenylacetaldehyde

(1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
5843-65-2, 17072-47-8, 106032-53-5, 22672-77-1

(1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Conditions
ConditionsYield
With CjNCS2 In acetonitrile at 37℃; for 3h; pH=7.4; Enzymatic reaction;99%
With recombinant Thalictrum flavum norcoclaurine synthase; 2-amino-2-hydroxymethyl-1,3-propanediol In methanol; water at 20℃; for 3h; pH=7; Pictet-Spengler cyclisation; Enzymatic reaction; enantioselective reaction;
With Norcoclaurine synthase Enzymatic reaction;
dopamine
51-61-6

dopamine

(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

N-oleoyldopamine
105955-11-1

N-oleoyldopamine

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 5h; Cooling with ice;97%
dopamine
51-61-6

dopamine

chloral
75-87-6

chloral

1-trichloromethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
115710-37-7

1-trichloromethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With trifluoroacetic acid Heating;95%
dopamine
51-61-6

dopamine

D-(+)-ribonic acid gamma-lactone

D-(+)-ribonic acid gamma-lactone

dopamine ribonamide

dopamine ribonamide

Conditions
ConditionsYield
Stage #1: dopamine; D-(+)-ribonic acid gamma-lactone In methanol for 0.166667h;
Stage #2: With triethylamine In methanol for 4h; Reflux; Darkness;
94.1%
dopamine
51-61-6

dopamine

cis-dichlorobis(triphenylphosphine)platinum(II)
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

Pt(P(C6H5)3)2(O2C6H3CH2CH2NH2)*0.5CH2Cl2

Pt(P(C6H5)3)2(O2C6H3CH2CH2NH2)*0.5CH2Cl2

Conditions
ConditionsYield
With potassium hydroxide; dichloromethane In methanol; benzene to a suspn. of substituted catechol in benzene was added MeOH soln. of KOH; prepd. soln. was syringed into suspn. of Pt complex in benzene; stirring at room temp. for 3.5 h (Ar); filtration, evapn., washing with water, drying in vac., dissoln. in CH2Cl2, filtration, evapn., washing with ether, drying in vac.; elem. anal.;94%
dopamine
51-61-6

dopamine

demethyldihydrocorynantheine
75991-86-5

demethyldihydrocorynantheine

3-[(E)-2-(3,4-Dihydroxy-phenyl)-ethylimino]-2-((2S,3R,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-propionic acid methyl ester

3-[(E)-2-(3,4-Dihydroxy-phenyl)-ethylimino]-2-((2S,3R,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-propionic acid methyl ester

Conditions
ConditionsYield
In methanol for 4h; Ambient temperature;93%
dopamine
51-61-6

dopamine

6-nitrodopamine hydrogen sulphate

6-nitrodopamine hydrogen sulphate

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite93%
dopamine
51-61-6

dopamine

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Conditions
ConditionsYield
With pyridine; 1,1,1,3',3',3'-hexafluoro-propanol for 8h; Pictet-Spengler Synthesis; Reflux; Inert atmosphere;93%
dopamine
51-61-6

dopamine

<5,6,8,9,11,12,14,15-3H8>arachidonic acid
66753-05-7

<5,6,8,9,11,12,14,15-3H8>arachidonic acid

N-[5,6,8,9,11,12,14,15-3H8]arachidonoyl-3-hydroxytyramine

N-[5,6,8,9,11,12,14,15-3H8]arachidonoyl-3-hydroxytyramine

Conditions
ConditionsYield
Stage #1: <5,6,8,9,11,12,14,15-3H8>arachidonic acid With triethylamine; isobutyl chloroformate In acetonitrile at 23℃; for 2h;
Stage #2: dopamine In N,N-dimethyl-formamide at 23℃; for 20h;
91%
dopamine
51-61-6

dopamine

1-chloro-7-methoxy-4-nitro-10H-acridin-9-one
21814-48-2

1-chloro-7-methoxy-4-nitro-10H-acridin-9-one

1-((3,4-dihydroxyphenethyl)amino)-7-methoxy-4-nitroacridin-9(10H)-one

1-((3,4-dihydroxyphenethyl)amino)-7-methoxy-4-nitroacridin-9(10H)-one

Conditions
ConditionsYield
With caesium carbonate In 1,4-dioxane for 9h; Heating;90.1%
dopamine
51-61-6

dopamine

3,4-Dihydroxyphenylacetaldehyde
5707-55-1

3,4-Dihydroxyphenylacetaldehyde

Conditions
ConditionsYield
With Halomonas elongata/Co imm pyridoxal phosphate In toluene at 37℃; for 0.25h; pH=7.5; Flow reactor; Enzymatic reaction;90%
With monoamine oxidases
With transaminase from chromobacterium violaceum; sodium pyruvate Enzymatic reaction;
dopamine
51-61-6

dopamine

phthalic anhydride
85-44-9

phthalic anhydride

2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline
57894-18-5

2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline

Conditions
ConditionsYield
at 100 - 150℃; Green chemistry;90%
dopamine
51-61-6

dopamine

formic acid
64-18-6

formic acid

chloral
75-87-6

chloral

6,7-Dihydroxy-1-trichloromethyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
115684-30-5

6,7-Dihydroxy-1-trichloromethyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde

Conditions
ConditionsYield
Heating;89%
dopamine
51-61-6

dopamine

6-mercaptocaproic acid
17689-17-7

6-mercaptocaproic acid

C14H21NO3S

C14H21NO3S

Conditions
ConditionsYield
Stage #1: 6-mercaptocaproic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.25h;
Stage #2: dopamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3h;
89%
dopamine
51-61-6

dopamine

1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

triethylamine
121-44-8

triethylamine

2,4,6-Tris-(2-[3,4-dimethoxyphenyl]ethylamino)-1,3,5-triazine

2,4,6-Tris-(2-[3,4-dimethoxyphenyl]ethylamino)-1,3,5-triazine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Cooling with ice;86%
dopamine
51-61-6

dopamine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)dopamine
37034-31-4

N-(tert-butoxycarbonyl)dopamine

Conditions
ConditionsYield
With TEA In methanol for 0.5h;85.5%
With sodium hydroxide; potassium hydrogensulfate In 1,4-dioxane; water; ethyl acetate2.6 g (78%)
dopamine
51-61-6

dopamine

2,3-dimethyoxybenzaldehyde
86-51-1

2,3-dimethyoxybenzaldehyde

4-(2-{[1-(2,3-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-ethyl)-benzene-1,2-diol

4-(2-{[1-(2,3-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-ethyl)-benzene-1,2-diol

Conditions
ConditionsYield
at 110℃; for 1h;85%
dopamine
51-61-6

dopamine

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

diethyl 3,4-dihydroxyphenethylphosphoramidate

diethyl 3,4-dihydroxyphenethylphosphoramidate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 5 - 40℃; for 2h;85%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

dopamine
51-61-6

dopamine

2-(3,4-dihydroxyphenyl)-N-((E)-3-phenylallylidene)ethanamine

2-(3,4-dihydroxyphenyl)-N-((E)-3-phenylallylidene)ethanamine

Conditions
ConditionsYield
In methanol for 24h; Reagent/catalyst; Reflux;83%
dopamine
51-61-6

dopamine

benzyl chloroformate
501-53-1

benzyl chloroformate

N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine
37034-22-3

N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine

Conditions
ConditionsYield
With sodium carbonate In diethyl ether; water at 0 - 20℃; for 3h;82%
With diethyl ether; sodium hydrogencarbonate
With sodium hydroxide In water; toluene at 5 - 10℃; for 2h;
dopamine
51-61-6

dopamine

diethylenetriaminepentaacetic dianhydride
23911-26-4

diethylenetriaminepentaacetic dianhydride

N,N'-bis(3-hydroxytyramide)diethylenetriamine N,N',N''-triacetic Acid
147666-97-5

N,N'-bis(3-hydroxytyramide)diethylenetriamine N,N',N''-triacetic Acid

Conditions
ConditionsYield
With ascorbic acid In N,N-dimethyl-formamide at 60℃;79%
dopamine
51-61-6

dopamine

phenyl isocyanate
103-71-9

phenyl isocyanate

1-[2-(3,4-dihydroxy-phenyl)-ethyl]-3-phenyl-urea

1-[2-(3,4-dihydroxy-phenyl)-ethyl]-3-phenyl-urea

Conditions
ConditionsYield
With pyridine for 6h;78%
dopamine
51-61-6

dopamine

Cyclohexyl isocyanate
3173-53-3

Cyclohexyl isocyanate

1-cyclohexyl-3-[2-(3,4-dihydroxy-phenyl)-ethyl]-urea

1-cyclohexyl-3-[2-(3,4-dihydroxy-phenyl)-ethyl]-urea

Conditions
ConditionsYield
With pyridine for 6h;78%
dopamine
51-61-6

dopamine

linoleic acid
60-33-3

linoleic acid

(Z,Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]-octadeca-9,12-dienamide
105955-12-2

(Z,Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]-octadeca-9,12-dienamide

Conditions
ConditionsYield
Stage #1: linoleic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: dopamine In dichloromethane for 12h;
77%
Stage #1: linoleic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In ethyl acetate at 20℃; for 1h;
Stage #2: dopamine In ethyl acetate at 20℃; for 12h;
dopamine
51-61-6

dopamine

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

(9H-fluoren-9-yl)methyl (3,4-dihydroxyphenethyl)carbamate

(9H-fluoren-9-yl)methyl (3,4-dihydroxyphenethyl)carbamate

Conditions
ConditionsYield
Stage #1: dopamine With sodium hydrogencarbonate In water at 0℃; for 0.25h;
Stage #2: (fluorenylmethoxy)carbonyl chloride In water; acetonitrile at 0 - 20℃; for 17.5h;
77%
Stage #1: dopamine With sodium hydrogencarbonate In water at 0℃; for 0.25h;
Stage #2: (fluorenylmethoxy)carbonyl chloride In acetonitrile at 0 - 20℃; for 17.5h;
77%
In water at 60℃; for 4h; chemoselective reaction;75%
dopamine
51-61-6

dopamine

p-bromophenylacetaldehyde
27200-79-9

p-bromophenylacetaldehyde

(1S)-1-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
1421820-24-7

(1S)-1-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Conditions
ConditionsYield
With CjNCS2 In acetonitrile at 37℃; for 3h; pH=7.4; Enzymatic reaction;77%
dopamine
51-61-6

dopamine

4-diphenylphosphanobenzoic acid
2129-31-9

4-diphenylphosphanobenzoic acid

C27H24NO3P
1439488-81-9

C27H24NO3P

Conditions
ConditionsYield
Stage #1: 4-diphenylphosphanobenzoic acid With N-Bromosuccinimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 2h;
Stage #2: dopamine With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 25℃;
76.8%
dopamine
51-61-6

dopamine

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-(2-((4-hydroxybenzylidene)amino)ethyl)benzene-1,2-diol

4-(2-((4-hydroxybenzylidene)amino)ethyl)benzene-1,2-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid; acetic acid In methanol Molecular sieve; Dean-Stark; Reflux;76%

Dopamine History

The function of Dopamine (CAS NO.51-61-6) as a neurotransmitter was discovered in 1958 by Arvid Carlsson and Nils-?ke Hillarp at the Laboratory for Chemical Pharmacology of the National Heart Institute of Sweden. It was named dopamine(51-61-6) because it was a monoamine, and its synthetic precursor was 3,4-dihydroxyphenylalanine (L-DOPA). Arvid Carlsson was awarded the 2000 Nobel Prize in Physiology or Medicine for showing that dopamine(51-61-6) is not just a precursor of norepinephrine (noradrenaline) and epinephrine (adrenaline) but a neurotransmitter, as well.
Dopamine(51-61-6) was first synthesized in 1910 by George Barger and James Ewens at Wellcome Laboratories in London, England.

Dopamine Specification

The CAS registry number of Dopamine is 51-61-6. In addition, the molecular formula is C8H11NO2. It is a catecholamine neurotransmitter which present in a wide variety of animals, including both vertebrates and invertebrates. And it is produced in several areas of the brain, including the substantia nigra and the ventral tegmental area. Moreover, its main function as a hormone is to inhibit the release of prolactin from the anterior lobe of the pituitary.

Physical properties about this chemical are: (1)ACD/LogP: 0.05; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 3; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 66.48 Å2; (10)Index of Refraction: 1.619; (11)Molar Refractivity: 43.101 cm3; (12)Molar Volume: 122.788 cm3; (13)Polarizability: 17.086 ×10-24cm3; (14)Surface Tension: 60.841 dyne/cm; (15)Density: 1.248 g/cm3; (16)Flash Point: 158.03 °C; (17)Enthalpy of Vaporization: 60.399 kJ/mol; (18)Boiling Point: 337.69 °C at 760 mmHg.

Preparation of Dopamine: it is synthesized by demethylation of 2-(3,4-dimethoxyphenyl)ethylamine through using hydrogen bromide.

Dopamine is synthesized by demethylation of 2-(3,4-dimethoxyphenyl)ethylamine through using hydrogen bromide

Uses of Dopamine: it can be used as a medicinal agent. And it is available as an intravenous medication acting on the sympathetic nervous system, and can increase heart rate and blood pressure. In addition, it can react with N-Methoxydiacetamide to get N-(3,4-dihydroxy-phenethyl)-acetamide. This reaction will need reagent sodium acetate and solvent dimethylformamide. The reaction time is 4.5 hours with ambient temperature. The yield is about 31%.

Dopamine can react with N-Methoxydiacetamide to get N-(3,4-dihydroxy-phenethyl)-acetamide

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(cc1CCN)O)O
(2)InChI: InChI=1/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
(3)InChIKey: VYFYYTLLBUKUHU-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 1120mg/kg (1120mg/kg)   Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 24(4), Pg. 42, 1990.
mouse LD50 intracervical 74mg/kg (74mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Tohoku Yakka Daigaku Kenkyu Nempo. Annual Report of the Tohoku College of Pharmacy. Vol. 27, Pg. 131, 1980.
mouse LD50 intraperitoneal 950mg/kg (950mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: HEMORRHAGE
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 835, 1974.
mouse LD50 intravenous 59mg/kg (59mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: HEMORRHAGE
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 835, 1974.
rat LD50 intraperitoneal 163mg/kg (163mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Toxicology and Applied Pharmacology. Vol. 88, Pg. 433, 1987.

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