CAS Number16290-26-9
SynonymsEINECS 240-382-8; 4-(Aminomethyl)catechol hydrobromide,DHBA hydrobromide; MFCD00012859; 4-(aminomethyl)benzene-1,2-diol,hydrobromide; 3,4-Dihydroxybenzylamine hydrobromide
Molecular Formula(HO)2C6H3CH2NH2 · HBr
Molecular Weight220.06
Purity98%
Density1.309g/cm3
Boiling Point333.4ºC at 760mmHg
Melting Point184-186 °C (lit.)
Appearancecrystals
EINECS240-382-8
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 16290-26-9 |
| Catalog No. | 2A-9083750 |
| Chinese Name | 3,4-二羟基苄胺氢溴酸 |
| Synonyms | EINECS 240-382-8; 4-(Aminomethyl)catechol hydrobromide,DHBA hydrobromide; MFCD00012859; 4-(aminomethyl)benzene-1,2-diol,hydrobromide; 3,4-Dihydroxybenzylamine hydrobromide |
| Molecular Formula | (HO)2C6H3CH2NH2 · HBr |
| Molecular Weight | 220.06 |
| Purity | 98 |
| Density | 1.309g/cm3 |
| Boiling Point | 333.4ºC at 760mmHg |
| Melting Point | 184-186 °C (lit.) |
| Appearance | crystals |
| Storage Condition | Sealed at room temperature, protected from light, |
| Application | 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) is a structurally modified dopamine analog cytotoxic agent that inhibits DNA polymerase activity in melanoma cells. 3,4-Dihydroxybenzyla |
| EINECS | 240-382-8 |
| HTC | 2922299090 |
| PubChem ID | 24888473 |
| MDL Number | MFCD00012859 |
| SMILES | 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 |
| Beilstein/REAXYS | 4002646 |
| NACRES Code | NA.22 |
| UNSPSC | 12352100 |
| Hazard Symbols | transportation |
| MSDS | msds/83750_1_16290_26_9.pdf |
| Bioactivity | 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) is an improved dopamine analog cytotoxic and inhibits DNA polymerase activity in melanoma cells[2]. 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) displays growth inhibitory activity in melanoma cell lines with varying degrees of tyrosinase activity[2]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis In Vitro 3,4-Dihydroxybenzylamine hydrobromide (1 μM-10 mM; 48 hours) inhibits the growth of all melanoma cell lines with an IC50 of 100 μM, while the SK-MELB cell line exhibits an IC50 of 122 μM. The IC50 values are 30, 84,90, and 68 μM for Human SK-MEL-30, SK-MEL-2, SK-MEL-3,RPMI-7951 cells, respectively. It exhibits IC50values of 10, 25, 67, and 184 μM for S91A,S91B, L1210, and SCC-25 cells, respectively[2]. 3,4-Dihydroxybenzylamine hydrobromide (1 μM-10 mM; 48 hours) cytotoxicity in SK-MEL-2 and SK-MEL-28 cell lines can be enhanced by application of buthionine sulfoximine (BSO). BSO treatment sensitizes marginally pigmented cells to the effects of 3,4-DHBA, and the presence of decreses IC50 values of 3,4-DHBA by 127% in the SK-MEL-28 cell line and by 148% in the SK-MEL-2 cell line[2]. Cell Viability Assay[1] Cell Line: Human and Murine Melanoma Cell Lines; Non-Melanoma Cell Lines Concentration: 1 μM-10 mM Incubation Time: 48 hours Result: Inhibited melanoma cell Lines growth. In Vivo 3,4-Dihydroxybenzylamine hydrobromide (intraperitoneal injection; 1000 mg/kg; 7 days) has the least toxic effect in non-tumor-bearing B6D2F1 mice,and mice is tolerated at this dose[3]. 3,4-Dihydroxybenzylamine hydrobromide (intraperitoneal injection; 200-800 mg/kg; 21 days) has different effects at different doses, the median life-span are 17, 24.5, 26, 29 and 25 days for 0 mg/kg, 200 mg/kg, 400 mg/kg, 600 mg/kg, and 800 mg/kg, respectively[3]. Animal Model: C57BL/6 mice with B6D2F1 cells[3] Dosage: 200 mg/kg, 400 mg/kg, 600 mg/kg, and 800 mg/kg Administration: Intraperitoneal injection Result: Exhibited increased life-span of 44%,46%, 70% and 50% for 200 mg/kg, 400 mg/kg, 600 mg/kg, and 800 mg/kg, respectively. 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. Chemical & Physical Properties Density 1.309g/cm3 Boiling Point 333.4ºC at 760mmHg Melting Point 184-186 °C(lit.) Molecular Formula C7H10BrNO2 Molecular Weight 220.06400 Flash Point 155.5ºC Exact Mass 218.98900 PSA 66.48000 LogP 2.21490 Vapour Pressure 1.32E-05mmHg at 25°C |
| Use of | 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) is an improved dopamine analog cytotoxic and inhibits DNA polymerase activity in melanoma cells[2]. 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) displays growth inhibitory activity in melanoma cell lines with varying degrees of tyrosinase activity[2]. Properties Articles28 Name 3,4-dihydroxybenzylamine hydrobromide Synonym More Synonyms 3,4-DIHYDROXYBENZYLAMINE HYDROBROMIDE Biological Activity Description 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) is an improved dopamine analog cytotoxic and inhibits DNA polymerase activity in melanoma cells[2]. 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) displays growth inhibitory activity in melanoma cell lines with varying degrees of tyrosinase activity[2]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis 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. Chemical & Physical Properties Molecular Formula C7H10BrNO2 Exact Mass 218.98900 PSA 66.48000 LogP 2.21490 |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 30.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available The above information is believed to be correct, but is not all-inclusive and should be used as a guide only. The information in this document is based on our current knowledge and is Correct safety instructions apply to this product. This information does not represent a warranty as to the properties of this product. See reverse side of invoice or packing slip. |
| Related Products in Specialty Chemicals | ||
|---|---|---|
| Phenylphosphorodiamidate | 7450-69-3 | 2A-9083742 |
| Phenyltrimethylammoniummethosulfate | 28001-58-3 | 2A-9083744 |
| 4-N-Propylbenzenesulfonylchloride | 63014-04-0 | 2A-9083745 |
| 7-Tetradecanol | 3981-79-1 | 2A-9083746 |
| 2,3,5,6-Tetramethylbenzenesulfonylchloride | 60706-63-0 | 2A-9083747 |
| Diethylsulfone | 597-35-3 | 2A-9083762 |
| 2,2-Bis(4-fluorophenyl)ethanamine | 98383-56-3 | 2A-9083763 |
| 7-Amino-2(1H)-quinoxalinone | 98555-00-1 | 2A-9083764 |
| Diethyl4-aminobenzylphosphonate | 20074-79-7 | 2A-9083768 |
| Aphidicolin | 38966-21-1 | 2A-9083770 |
| Browse all Specialty Chemicals products » | ||
Phone:
630-322-8886
630-322-8887
Email:
Office Locations:
Chicago, IL, USA
San Francisco, CA, USA
EN
SDS