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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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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
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
Ki Sung Kang et al.
PloS one, 5(8), e11951-e11951 (2010-08-12)
A combination of levodopa (L-DOPA) and carbidopa is the most commonly-used treatment for symptom management in Parkinson's disease. Studies have shown that concomitant use of a COMT inhibitor is highly beneficial in controlling the wearing-off phenomenon by improving L-DOPA bioavailability
J A Prezioso et al.
The Journal of investigative dermatology, 99(3), 289-293 (1992-09-01)
Buthionine sulfoximine (BSO), a specific inhibitor of glutathione synthesis, showed variable growth-inhibitory activity in different tumor cell lines with a high degree of inhibitory activity against melanoma-derived cell lines. A correlation between BSO growth-inhibitory effects and cellular glutathione peroxidase activity
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

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