3-O-Methyldopamine hydrochloride

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CAS:1477-68-5
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3-O-Methyldopamine hydrochloride manufacturers

  • Dopamine Impurity 4
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  • $0.00 / 10mg
  • 2025-09-25
  • CAS:1477-68-5
  • Min. Order: 10mg
  • Purity: 98%
  • Supply Ability: 500mg
  • Dopamine Impurity 4
  • Dopamine Impurity 4 pictures
  • $0.00 / 10mg
  • 2025-09-25
  • CAS:1477-68-5
  • Min. Order: 10mg
  • Purity: 0.98
  • Supply Ability: 10g
3-O-Methyldopamine hydrochloride Basic information
Product Name:3-O-Methyldopamine hydrochloride
Synonyms:3-O-Methyldopanimehydrochloride;3-O-Methyldopamine hydrochloride, p.a.;RARECHEM AL BW 0216;TIMTEC-BB SBB000426;TIMTEC-BB SBB003882;3-METHOXY-4-HYDROXY-PHENETHYLAMINE HYDROCHLORIDE;3-METHOXY-4-HYDROXYPHENYLETHYLAMINE, HCL;3-O-METHYLDOPAMINE HYDROCHLORIDE
CAS:1477-68-5
MF:C9H13NO2.ClH
MW:203.67
EINECS:216-035-1
Product Categories:Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Bioactive Small Molecules;Building Blocks;C9 to C20+;Cell Biology;Chemical Synthesis;M;Organic Building Blocks;Oxygen Compounds;Phenols
Mol File:1477-68-5.mol
3-O-Methyldopamine hydrochloride Structure
3-O-Methyldopamine hydrochloride Chemical Properties
Melting point 213-215 °C(lit.)
Fp 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.
InChIInChI=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
InChIKeyAWRIOTVUTPLWLF-UHFFFAOYSA-N
SMILESC1(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
3-10
HazardClass IRRITANT
HS Code 29222990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
3-O-Methyldopamine hydrochloride Usage And Synthesis
Chemical Propertieslight beige crystalline solid
Uses3-Methoxy-p-tyramine is a major metabolite of Dopamine (D533780); product of catechol O-methyltransferase.
General Description3-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 ActionsMajor metabolite of dopamine; product of catechol O-methyltransferase.
Synthesis
Phenol, 2-methoxy-4-(2-nitroethyl)- (9CI)

528594-30-1

3-O-Methyldopamine hydrochloride

1477-68-5

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

The extracellular DA metabolite 3-Methoxytyramine hydrochloride (3-MT) induces significant behavioral activation in DDD mice. This activity however, is mostly presented as a set of disorganized abnormal movements that includes tremor, head bobbing, straub tail, grooming and abnormal orofacial movements rather than normal forward activity. No effect is observed when 3-Methoxytyramine hydrochloride is infused at doses below 9 μg, at 9 μg and higher doses 3-Methoxytyramine hydrochloride dose-dependently causes transient behavioral activation with a complex set of behaviors. In particular, transient hyperactivity and stereotypy, sniffing, grooming, rearing and mild abnormal involuntary movements (AIMs) at the level of limbs is observed after infusion of 9 μg of 3-Methoxytyramine hydrochloride. Similar behaviors are also observed after 18 μg of 3-Methoxytyramine hydrochloride with the additional appearance of tremor as well as oral and whole body AIMs[1].

IC 50Human 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
Tag:3-O-Methyldopamine hydrochloride(1477-68-5) Related Product Information
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