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1477-68-5

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1477-68-5 Usage

Chemical Properties

light beige crystalline solid

Uses

3-Methoxy-p-tyramine is a major metabolite of Dopamine (D533780); product of catechol O-methyltransferase.

General Description

3-Methoxytyramine is a metabolite of dopamine, a catecholamine which acts as a neurotransmitter for dopamine receptors and a neurohormone for regulation of numerous brain functions. 3-Methoxytyramine levels can serve as a biomarker for the diagnosis of neuroendocrine tumors such as pheochromocytoma or paraganglioma. This certified solution standard is suitable for LC/MS applications in diagnostic testing, endocrinology, and clinical chemistry.

Biochem/physiol Actions

Major metabolite of dopamine; product of catechol O-methyltransferase.

Check Digit Verification of cas no

The CAS Registry Mumber 1477-68-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,7 and 7 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1477-68:
(6*1)+(5*4)+(4*7)+(3*7)+(2*6)+(1*8)=95
95 % 10 = 5
So 1477-68-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H13NO2.ClH/c1-12-9-3-2-7(4-5-10)6-8(9)11;/h2-3,6,11H,4-5,10H2,1H3;1H

1477-68-5 Well-known Company Product Price

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  • Sigma

  • (M4251)  3-Methoxytyraminehydrochloride  ≥95.5%, crystalline

  • 1477-68-5

  • M4251-100MG

  • 734.76CNY

  • Detail
  • Sigma

  • (M4251)  3-Methoxytyraminehydrochloride  ≥95.5%, crystalline

  • 1477-68-5

  • M4251-1G

  • 4,151.16CNY

  • Detail

1477-68-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-O-Methyldopamine hydrochloride

1.2 Other means of identification

Product number -
Other names 4-(2-aminoethyl)-2-methoxyphenol,hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1477-68-5 SDS

1477-68-5Synthetic route

4-hydroxy-3-methoxyphenylacetonitrile
4468-59-1

4-hydroxy-3-methoxyphenylacetonitrile

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 12h;82%
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol under 7600 - 11400 Torr; for 1.5h;75%
vanillalnitromethane
6178-42-3

vanillalnitromethane

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 0℃; under 760 Torr;81%
With hydrogenchloride; zinc In ethanol; water at 40 - 60℃; for 3h;67.08%
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C
2.1: hydrogenchloride; zinc / ethyl acetate; water / 3 h / 50 - 70 °C
2.2: 2 h / -20 °C
View Scheme
3-methoxy-4-benzyloxy-ω-nitrostyrolene
63909-38-6, 1860-56-6

3-methoxy-4-benzyloxy-ω-nitrostyrolene

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; iron(III) chloride; platinum In water for 4h;76%
2-methoxy-4-(2-nitroethyl)phenol
528594-30-1

2-methoxy-4-(2-nitroethyl)phenol

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-(2-nitroethyl)phenol With hydrogenchloride; zinc In water; ethyl acetate at 50 - 70℃; for 3h;
Stage #2: With hydrogenchloride In methanol at -20℃; for 2h;
72%
Stage #1: 2-methoxy-4-(2-nitroethyl)phenol With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;
Stage #2: With hydrogenchloride In water
31%
3-methoxy-4-(phenylmethoxy)benzaldehyde
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C
2: 85 percent / AcONa. Ac2O / 0.08 h / Heating
3: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h
View Scheme
Multi-step reaction with 2 steps
1: 72 percent / KOH / aq. ethanol / 2 h / 0 °C
2: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h
View Scheme
1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol
60372-07-8

1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / AcONa. Ac2O / 0.08 h / Heating
2: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h
View Scheme
vanillin
121-33-5

vanillin

<4-oxy-3-methoxy-phenyl>-bis-<4-dimethylamino-phenyl>-methane

<4-oxy-3-methoxy-phenyl>-bis-<4-dimethylamino-phenyl>-methane

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C
2: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C
3: 85 percent / AcONa. Ac2O / 0.08 h / Heating
4: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C
2: 72 percent / KOH / aq. ethanol / 2 h / 0 °C
3: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h
View Scheme
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / dimethylformamide / 20 h / 130 °C
2: 82 percent / H2; HCl / Pd/C / ethanol / 12 h / 20 °C
View Scheme
2-(4-hydroxy-3-methoxyphenyl)acetamide
29121-49-1

2-(4-hydroxy-3-methoxyphenyl)acetamide

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
Stage #1: 2-(4-hydroxy-3-methoxyphenyl)acetamide With borane-THF In tetrahydrofuran at 0℃; for 8h; Reflux;
Stage #2: With hydrogenchloride In water for 3h; Reflux;
54.2 g
vanillin
121-33-5

vanillin

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol; methylamine / 2 h / 50 °C
2.1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C
3.1: hydrogenchloride; zinc / ethyl acetate; water / 3 h / 50 - 70 °C
3.2: 2 h / -20 °C
View Scheme
Multi-step reaction with 3 steps
1: ethylenediamine / 4 h / Reflux
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 0 - 20 °C
3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
View Scheme
3,4-dimethylphenylacetic acid
17283-16-8

3,4-dimethylphenylacetic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

2-(3,4-dimethylphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

2-(3,4-dimethylphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;100%
3-nitro-benzeneacetic acid
1877-73-2

3-nitro-benzeneacetic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(3-nitrophenyl)acetamide

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(3-nitrophenyl)acetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;100%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

2-naphthylacetic acid
581-96-4

2-naphthylacetic acid

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(naphthalen-2-yl)acetamide

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(naphthalen-2-yl)acetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;100%
2-[4-(dimethylamino)phenyl]acetic acid
17078-28-3

2-[4-(dimethylamino)phenyl]acetic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

2-[4-(dimethylamino)phenyl]-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

2-[4-(dimethylamino)phenyl]-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;99%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

methyl chloroformate
79-22-1

methyl chloroformate

methyl 3-methoxy-4-((methoxycarbonyl)oxy)phenethylcarbamate

methyl 3-methoxy-4-((methoxycarbonyl)oxy)phenethylcarbamate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;99%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl(4-(2-isocyanatoethyl)-2-methoxyphenoxy)dimethylsilane

tert-butyl(4-(2-isocyanatoethyl)-2-methoxyphenoxy)dimethylsilane

Conditions
ConditionsYield
Stage #1: 3-Methoxytyramine hydrochloride With 1H-imidazole In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 3h; Inert atmosphere;
Stage #3: bis(trichloromethyl) carbonate In toluene at 20 - 100℃; for 1.5h; Inert atmosphere;
98%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethanamine

2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethanamine

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 3h; Inert atmosphere;97%
4-benzyloxy-3-methoxyphenylacetic acid
29973-91-9

4-benzyloxy-3-methoxyphenylacetic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

2-[4-(benzyloxy)-3-methoxyphenyl]-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide
60917-45-5

2-[4-(benzyloxy)-3-methoxyphenyl]-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;96%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

3'-O-methyl-N-oleoyl-dopamine

3'-O-methyl-N-oleoyl-dopamine

Conditions
ConditionsYield
With triethanolamine; benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; for 15.25h;92%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-3-O-methyldopamine
10211-09-3

N-acetyl-3-O-methyldopamine

Conditions
ConditionsYield
With potassium carbonate; triethylamine In methanol; chloroform91%
With triethylamine In dichloromethane at 20℃; for 0.5h;87%
(3,4-Dimethoxyphenyl)acetic acid
93-40-3

(3,4-Dimethoxyphenyl)acetic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

2-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide
1451411-31-6

2-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;91%
o-methylmandelic acid
85589-35-1

o-methylmandelic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

2-(2-bromophenyl)-2-hydroxy-N-(4-hydroxy-3-methoxyphenethyl)acetamide

2-(2-bromophenyl)-2-hydroxy-N-(4-hydroxy-3-methoxyphenethyl)acetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;82%
carbon dioxide
124-38-9

carbon dioxide

triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

C19H33NO4Si
391609-22-6

C19H33NO4Si

Conditions
ConditionsYield
Stage #1: carbon dioxide; 3-Methoxytyramine hydrochloride In dichloromethane at -78℃; for 1h;
Stage #2: triisopropylsilyl trifluoromethanesulfonate at -78 - 20℃;
78%
With triethylamine In dichloromethane at -78℃;78%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

benzaldehyde
100-52-7

benzaldehyde

6-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol
72105-97-6

6-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol

Conditions
ConditionsYield
Stage #1: 3-Methoxytyramine hydrochloride; benzaldehyde With magnesium sulphate; triethylamine In methanol for 3h; Reflux;
Stage #2: With trifluoroacetic acid In ethyl acetate for 1h; Reflux;
Stage #3: With sodium hydrogencarbonate
74%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

trimethyl orthoformate
149-73-5

trimethyl orthoformate

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide
282721-32-8

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide

Conditions
ConditionsYield
for 2h; Heating;71%
(4-isopropylphenyl)acetic acid
4476-28-2

(4-isopropylphenyl)acetic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;71%
formaldehyd
50-00-0

formaldehyd

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

1,2,3,4-tetrahydro-6-methoxy-7-isoquinolinol hydrochloride
1078-26-8

1,2,3,4-tetrahydro-6-methoxy-7-isoquinolinol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 70℃; for 1h; Pictet-Spengler isoquinoline synthesis;70%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

S-(2-naphthylmethyl)thioacetimidate hydrobromide

S-(2-naphthylmethyl)thioacetimidate hydrobromide

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

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

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 3h;70%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

dopamine hydrochloride
62-31-7

dopamine hydrochloride

Conditions
ConditionsYield
Stage #1: 3-Methoxytyramine hydrochloride With hydrogen bromide for 6h; Reflux;
Stage #2: With hydrogenchloride In water
69.81%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

2-(3-(dimethylamino)phenyl)acetic acid

2-(3-(dimethylamino)phenyl)acetic acid

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]acetamide

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]acetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;69%
formic acid
64-18-6

formic acid

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide
282721-32-8

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide

Conditions
ConditionsYield
Stage #1: formic acid With acetic anhydride at 55℃; for 2h;
Stage #2: 3-Methoxytyramine hydrochloride In tetrahydrofuran at 75℃; for 16h; Further stages.;
66%
Stage #1: formic acid With acetic anhydride at 0 - 55℃; for 2h;
Stage #2: 3-Methoxytyramine hydrochloride In tetrahydrofuran at 0 - 75℃; for 18h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate
23699-77-6

tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 24h;59%
With sodium hydrogencarbonate; triethylamine; citric acid In water; ethyl acetate
With triethylamine In dichloromethane at 20℃; for 18h;4.59 g
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

acetaldehyde
75-07-0

acetaldehyde

N-Nor-1-methylcorypalline
4593-97-9

N-Nor-1-methylcorypalline

Conditions
ConditionsYield
Stage #1: 3-Methoxytyramine hydrochloride; acetaldehyde With hydrogenchloride In water at 100℃; for 24h; Pressure tube;
Stage #2: With sodium hydrogencarbonate In water
55%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

acetaldehyde
75-07-0

acetaldehyde

Isosalsoline hydrochloride
98321-33-6

Isosalsoline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 24h; Sealed tube;55%
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

nonanoic acid N-hydroxysuccinimide ester
104943-23-9

nonanoic acid N-hydroxysuccinimide ester

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]nonanamide

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]nonanamide

Conditions
ConditionsYield
With triethylamine In ethyl acetate for 12h;46%
formaldehyd
50-00-0

formaldehyd

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

tert-butyl 7-hydroxy-6-methoxy-3,4-dihydroisoquinoline-2(1H)- carboxylate

tert-butyl 7-hydroxy-6-methoxy-3,4-dihydroisoquinoline-2(1H)- carboxylate

Conditions
ConditionsYield
Stage #1: formaldehyd; 3-Methoxytyramine hydrochloride With hydrogenchloride In water at 50℃; for 6h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 17h;
41.6%

1477-68-5Relevant articles and documents

Synthetic method of high-purity dopamine hydrochloride

-

Paragraph 0007-0008; 0052, (2020/11/23)

The invention provides a synthetic method of dopamine hydrochloride, and belongs to the field of drug synthesis. The preparation method comprises the following steps: taking 3,4-dimethoxyphenylethylamine as an initial raw material, firstly reacting with an acid to form a salt, re-crystallizing and refining to obtain 3,4-dimethoxyphenylethylamine salt, reacting with hydrobromic acid to remove methyl to generate dopamine hydrobromide, and finally reacting with hydrochloric acid to form a salt so as to obtain dopamine hydrochloride. The preparation method provided by the invention has the advantages of cheap and easily available initial raw materials, simple process, no high-temperature and high-pressure hydrogenation step, low cost, high purity and high yield, and is suitable for industrialproduction.

Total Synthesis of (-)-Melanthioidine by Copper-Mediated Cyclodimerization

Wang, Jianjun,Evano, Gwilherm

, p. 3542 - 3545 (2016/08/16)

An efficient asymmetric total synthesis of the dimeric macrocyclic diaryl ether phenethyltetrahydroisoquinoline alkaloid (-)-melanthiodine is reported. Key steps of the synthesis include an efficient Noyori asymmetric transfer hydrogenation to access the enantioenriched phenethyltetrahydroisoquinoline monomeric subunit and a copper-mediated cyclodimerization to form the two diaryl ether linkages with concomitant macrocyclization.

Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide

Jai, Woong Seo,Srisook, Ekaruth,Hyo, Jin Son,Hwang, Onyou,Cha, Young-Nam,Dae, Yoon Chi

, p. 3369 - 3373 (2007/10/03)

Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.

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