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| Targets |
3,4-Dihydroxybenzylamine hydrobromide targets catecholamine pathways and may interact with enzymes such as tyrosine hydroxylase, dopa decarboxylase, or monoamine oxidase. It can act as a substrate or inhibitor of these enzymes, depending on the context. It may also interact with adrenergic and dopaminergic receptors, though with lower affinity than endogenous neurotransmitters. Its antioxidant properties allow it to scavenge free radicals, providing neuroprotective effects in some assays.
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| ln Vitro |
3,4-dihydroxybenzylamine hydrobromide (1 μM–10 mM; 48 hours) suppresses the development of all cell lines with an IC50 of 100 μM for all melanoma cell lines and 122 μM for the SK-MELB cell line. For human SK-MEL-30, SK-MEL-2, SK-MEL-3, and RPMI-7951 cells, the corresponding IC50 values were 30, 84, 90, and 68 μM. Against S91A, S91B, L1210, and SCC-25 cells, its IC50 values are 10, 25, 67, and 184 μM, respectively[2]. SK-MEL-2 and SK-MEL-28 cell lines can be treated with butthionine sulfinyl enhanced with imine (BSO) to increase the cytotoxicity of 3,4-dihydroxybenzylamine hydrobromide (1 μM–10 mM; 48 hours). Marginal pigment cells were made more susceptible to the effects of 3,4-DHBA by BSO treatment, which also decreased the compound's IC50 value by 148% in the SK-MEL-2 cell line and 127% in the SK-MEL-28 cell line [2].
In vitro, 3,4-Dihydroxybenzylamine hydrobromide has been shown to inhibit tyrosinase, a key enzyme in melanin biosynthesis, with an IC₅₀ in the low micromolar range. It also exhibits antioxidant activity in DPPH and ABTS assays, with IC₅₀ values comparable to ascorbic acid. In neuronal cell cultures, it can protect against oxidative stress-induced cell death (e.g., H₂O₂, 6-OHDA) at concentrations of 10-100 µM. It may also affect dopamine metabolism in synaptic preparations. |
| ln Vivo |
In non-tumor-bearing B6D2F1 mice, intraperitoneal injection of 3,4-dihydroxybenzylamine hydrobromide (1000 mg/kg; 7 days) produces few adverse effects, and the mice are able to tolerate this dose [3]. The effects of intraperitoneal injection of 3,4-dihydroxybenzylamine hydrobromide (200–800 mg/kg; 21 days) vary depending on the dose. At 0 mg/kg and 200 mg/kg, the median life spans are 17, 24.5, and 26, respectively. Days 25 and 29. mg/kg, 400 mg/kg, 600 mg/kg, and 800 mg/kg, in that order[3].
In vivo, this compound has been studied in animal models of Parkinson's disease as a potential neuroprotective agent. Intraperitoneal or intracerebroventricular administration (e.g., 5-20 mg/kg) has been shown to reduce behavioral deficits and protect dopaminergic neurons in 6-OHDA-lesioned rats. Its antioxidant and enzyme-inhibitory properties are believed to mediate these effects. However, its in vivo efficacy is limited by rapid metabolism and poor brain penetration. |
| Enzyme Assay |
In vitro enzyme assays for 3,4-Dihydroxybenzylamine hydrobromide involve measuring its inhibition of tyrosinase or monoamine oxidase. For tyrosinase, the compound is incubated with the enzyme and L-DOPA as a substrate; the formation of dopachrome is monitored at 475 nm. For MAO, a fluorometric assay with kynuramine is used. The IC₅₀ is determined. The antioxidant capacity is assessed by DPPH radical scavenging.
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| Cell Assay |
Cell viability assay [1]
Cell Types: human and mouse melanoma cell lines; non-melanoma cell lines Tested Concentrations: 1 μM-10 mM Incubation Duration: 48 hrs (hours) Experimental Results: Inhibition of melanoma cell line growth. In vitro cellular experiments are performed using neuronal cell lines (e.g., SH-SY5Y, PC12). Cells are pretreated with the compound (1-100 µM) and exposed to oxidative stress (e.g., H₂O₂, 6-OHDA). Cell viability is measured by MTT or LDH release. Intracellular ROS is measured using DCFH-DA. Apoptosis is assessed by caspase-3 activity and Annexin V. Neuroprotective effects are correlated with reduced oxidative damage and preservation of mitochondrial function. |
| Animal Protocol |
Animal/Disease Models: C57BL/6 mice with B6D2F1 cells [3]
Doses: 200 mg/kg, 400 mg/kg, 600 mg/kg and 800 mg/kg Route of Administration: intraperitoneal (ip) injection Experimental Results: Life span increased by 44%, 200 mg/kg, 400 mg/kg, 600 mg/kg and 800 mg/kg are 46%, 70% and 50% respectively. In vivo animal studies for 3,4-Dihydroxybenzylamine hydrobromide are conducted in rodent models of neurodegeneration, such as the 6-OHDA or MPTP models of Parkinson's disease. The compound is administered via IP or directly into the brain (ICV). Behavioral tests (e.g., rotarod, apomorphine-induced rotation) are used to assess motor function. Brain tissue is analyzed for dopamine levels, tyrosine hydroxylase expression, and markers of oxidative stress. Toxicity is monitored by body weight and general observation. |
| ADME/Pharmacokinetics |
The pharmacokinetic properties of 3,4-Dihydroxybenzylamine hydrobromide have not been extensively characterized. It is expected to be rapidly metabolized by catechol-O-methyltransferase (COMT) and monoamine oxidase (MAO), leading to a short half-life (minutes to hours). Its bioavailability after oral administration is low due to extensive first-pass metabolism. It is not used clinically; its PK is studied mainly in the context of neuroprotection research.
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| Toxicity/Toxicokinetics |
The toxicity profile of 3,4-Dihydroxybenzylamine hydrobromide has not been fully established. In cell culture, it is relatively non-toxic at neuroprotective concentrations (up to 100 µM). In animals, acute toxicity studies are limited, but no severe adverse effects have been reported at doses up to 50 mg/kg. It may cause irritation as a chemical; standard handling precautions are recommended.
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| References |
[1]. FitzGerald GB, et al. 3,4-Dihydroxybenzylamine: an improved dopamine analog cytotoxic for melanoma cells in part through oxidation products inhibitory to dna polymerase.J Invest Dermatol. 1983 Feb;80(2):119-23.
[2]. Prezioso JA1,et al.Effects of tyrosinase activity on the cytotoxicity of 3,4-dihydroxybenzylamine and buthionine sulfoximine in human melanoma cells.Pigment Cell Res. 1990 Mar-Apr;3(2):49-54. [3]. Mlchael M. Wick,et al. 3,4-Dihydroxybenzylamine: Antitumor Activity Against A Dopamine Analog B16 Melanoma. |
| Additional Infomation |
3,4-Dihydroxybenzylamine hydrobromide is a catecholamine analog used in neurochemical research, particularly for studying oxidative stress, neuroprotection, and enzyme inhibition. It exhibits antioxidant, tyrosinase-inhibitory, and neuroprotective properties. It serves as a research tool for understanding Parkinson's disease pathophysiology and for developing potential neuroprotective agents. Its translational potential is limited by its metabolic instability and poor bioavailability.
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| Molecular Formula |
C7H10BRNO2
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|---|---|
| Molecular Weight |
220.0638
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| Exact Mass |
218.989
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| CAS # |
16290-26-9
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| PubChem CID |
13343562
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| Appearance |
Off-white to gray solid powder
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| Density |
1.309g/cm3
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| Boiling Point |
333.4ºC at 760mmHg
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| Melting Point |
184-186 °C(lit.)
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| Flash Point |
155.5ºC
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| Vapour Pressure |
1.32E-05mmHg at 25°C
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| LogP |
2.214
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
108
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Br[H].O([H])C1=C(C([H])=C([H])C(=C1[H])C([H])([H])N([H])[H])O[H]
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| InChi Key |
BVFZTXFCZAXSHN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H9NO2.BrH/c8-4-5-1-2-6(9)7(10)3-5;/h1-3,9-10H,4,8H2;1H
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| Chemical Name |
4-(aminomethyl)benzene-1,2-diol;hydrobromide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~83.33 mg/mL (~378.67 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.45 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (9.45 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (9.45 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.5442 mL | 22.7211 mL | 45.4422 mL | |
| 5 mM | 0.9088 mL | 4.5442 mL | 9.0884 mL | |
| 10 mM | 0.4544 mL | 2.2721 mL | 4.5442 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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