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16290-26-9

16290-26-9 structure
16290-26-9 structure
  • Name: 3,4-DIHYDROXYBENZYLAMINE HYDROBROMIDE
  • Chemical Name: 3,4-dihydroxybenzylamine hydrobromide
  • CAS Number: 16290-26-9
  • Molecular Formula: C7H10BrNO2
  • Molecular Weight: 220.06400
  • Catalog: Signaling Pathways Cell Cycle/DNA Damage DNA/RNA Synthesis
  • Create Date: 2018-05-28 08:00:00
  • Modify Date: 2024-01-12 00:47:52
  • 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].
Name 3,4-dihydroxybenzylamine hydrobromide
Synonyms EINECS 240-382-8
4-(Aminomethyl)catechol hydrobromide,DHBA hydrobromide
MFCD00012859
4-(aminomethyl)benzene-1,2-diol,hydrobromide
3,4-Dihydroxybenzylamine hydrobromide
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
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.
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
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2922299090
Precursor  0

DownStream  1

HS Code 2922299090
Summary 2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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