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858781

Sigma-Aldrich

3,4-Dihydroxybenzylamine hydrobromide

98%

Synonym(s):

4-(Aminomethyl)catechol hydrobromide, DHBA hydrobromide

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About This Item

Linear Formula:
(HO)2C6H3CH2NH2 · HBr
CAS Number:
Molecular Weight:
220.06
Beilstein:
4002646
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

crystals

mp

184-186 °C (lit.)

SMILES string

Br.NCc1ccc(O)c(O)c1

InChI

1S/C7H9NO2.BrH/c8-4-5-1-2-6(9)7(10)3-5;/h1-3,9-10H,4,8H2;1H

InChI key

BVFZTXFCZAXSHN-UHFFFAOYSA-N

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Application

<ul>
<li><strong>Oxidative Polymerization of 3,4-Dihydroxybenzylamine:</strong> 3,4-Dihydroxybenzylamine is used in the synthesis of poly[3,4-dihydroxybenzylamine] (PDHBA) by oxidative polymerization, exploring its application as a lower homolog of dopamine for potential use in synthetic pathways and materials science (Petran et al., 2023).</li>
<li><strong>Detection of Urinary Free Metanephrines:</strong> Utilizing 3,4-Dihydroxybenzylamine hydrobromide as an internal standard, this research enhances the detection accuracy of urinary free metanephrines for diagnosing pheochromocytomas and paragangliomas, showcasing its importance in clinical diagnostic applications (Wang et al., 2020).</li>
<li><strong>Development of HPLC-ECD Method:</strong> A study developed an HPLC-ECD method using 3,4-Dihydroxybenzylamine as an internal standard for the analysis of vitamin C in plasma, demonstrating the chemical&rsquo;s utility in enhancing analytical methodologies in biochemical research (Clark and Frank, 2016).</li>
<li><strong>Fluorescence Analysis of Catecholamines:</strong> 3,4-Dihydroxybenzylamine is used as an internal standard to determine catecholamines and related compounds in rat brain tissue, underlining its application in neurochemical analysis and research (Fonseca et al., 2017).</li>
</ul>

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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J A Prezioso et al.
Pigment cell research, 3(2), 49-54 (1990-03-01)
The rationale for melanoma specific dihydroxybenzene containing antitumor agents is based in part upon the ability of the enzyme tyrosinase to oxidize these pro drugs to toxic intermediates. In situ tyrosinase activity was demonstrated to be affected by both cell
E C Chan et al.
Rapid communications in mass spectrometry : RCM, 14(21), 1959-1964 (2000-11-21)
An assay of norepinephrine (NE), epinephrine (E), dopamine (DA), normetanephrine (NE) and metanephrine (MN) based on high-performance liquid chromatography (HPLC) in combination with atmospheric pressure chemical ionization mass spectrometry (APcI-MS) is described. The catecholamines and metanephrines were extracted from urine
F Boomsma et al.
Journal of cardiovascular pharmacology, 22(2), 198-202 (1993-08-01)
We noted rapid breakdown at 4 degrees and 20 degrees C of dopamine (DA) (but not of (nor)epinephrine and epinine) in pig plasma, but not in human plasma. The enzyme responsible appears to be a semicarbazide-sensitive amine oxidase (SSAO) because
H B He et al.
Journal of chromatography, 574(2), 213-218 (1992-02-14)
This paper describes the application of a window diagram technique to optimize the four components of eluent (sodium acetate, sodium heptanesulfonate, acetonitrile and pH adjusted by monochloroacetic acid), for complete separation of five catecholamine compounds and the internal standard (3,4-dihydroxybenzylamine
Sophie Bourcier et al.
European journal of mass spectrometry (Chichester, England), 9(4), 351-360 (2003-08-27)
Our research into neurotransmitters in a biological fluid presented an opportunity to investigate the fragmentations under low collision energy characterising benzyl-amines protonated under electrospray ionisation (ESI) conditions in a triple quadrupole mass spectrometer. In this work we present the breakdown

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