3-O-Methyldopamine hydrochloride Chemical Properties

Melting point:

213-215 °C(lit.)

Flash point:

9℃

storage temp. 

-20°C

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)

form 

crystalline

color 

white to light brown

BRN 

3631283

Stability:

Stable, but may be light sensitive. Combustible. Incompatible with strong oxidizing agents.

InChI

InChI=1S/C9H13NO2.ClH/c1-12-9-6-7(4-5-10)2-3-8(9)11;/h2-3,6,11H,4-5,10H2,1H3;1H

InChIKey

AWRIOTVUTPLWLF-UHFFFAOYSA-N

SMILES

C1(OC)C(O)=CC=C(CCN)C=1.Cl

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

3

F 

3-10

HazardClass 

IRRITANT

HS Code 

29222990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

3-O-Methyldopamine hydrochloride Usage And Synthesis

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.

Synthesis

General procedure for the synthesis of 4-(2-aminoethyl)-2-methoxyphenol hydrochloride from 2-methoxy-4-(2-nitroethyl)phenol: 2-methoxy-4-(2-nitroethyl)phenol (8 g, 40.6 mmol), ethyl acetate, and concentrated hydrochloric acid were added to a reaction flask and heated to 70 °C. Activated zinc powder (35.0 g, 546.5 mmol) was slowly added under vigorous stirring, followed by slow cooling to 50 °C. After the addition of zinc powder, the reaction was continued for 3 h, during which vigorous stirring was maintained and the reaction progress was monitored by TLC. After completion of the reaction, it was cooled to room temperature and filtered to remove the excess zinc powder. The filtrate was dried with anhydrous sodium sulfate, and the filtrate was collected after filtration again and concentrated to give the oily product 4-(2-aminoethyl)-2-methoxyphenol (6.7 g, 40.0 mmol). To the oily product was added 4 M hydrochloric acid-methanol solution, shaken well and then frozen at -20 °C for 2 hours. Filtration gave the precipitated solid, 3-methoxy-4-hydroxyphenethylamine hydrochloride (6 g, yield about 72%).

in vivo

IC 50

Human Endogenous Metabolite

References

[1] Patent: CN105481849, 2016, A. Location in patent: Paragraph 0251; 0252; 0253; 0254; 0257
[2] Organic Letters, 2016, vol. 18, # 15, p. 3542 - 3545

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