| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
DNA (via formation of DNA adducts). BBN itself is a procarcinogen; it is metabolized by cytochrome P450 enzymes (primarily in the liver) to reactive intermediates that alkylate DNA, leading to mutations in oncogenes and tumor suppressors.
|
|---|---|
| ln Vitro |
BBN is not typically tested for in vitro activity in cell-free systems. The relevant biological activity is its metabolite-induced DNA damage: it causes DNA alkylation, leading to base mispairing and mutations upon DNA replication.
|
| ln Vivo |
N-Butyl-N-(4-hydroxybutyl)nitrosamine (BBN; 0.05% solution in drinking water; 2 weeks duration) is a potent mutagen in mouse and rat urothelial tissue [1].
In vivo, BBN is the standard chemical inducer of bladder cancer in rodents. Oral administration (e.g., 0.05% in drinking water for 8-12 weeks) induces transitional cell carcinoma of the bladder in 80-100% of mice and rats, histologically comparable to human bladder tumorigenesis. |
| Enzyme Assay |
Not applicable. The mechanism involves metabolic activation, not direct enzyme binding. BBN (10-100 microM) is incubated with rat liver microsomes (S9 fraction) and NADPH to generate reactive metabolites. DNA adducts are then analyzed by 32P-postlabeling or mass spectrometry.
|
| Cell Assay |
Not typically performed, as BBN requires metabolic activation. Some in vitro genotoxicity assays are performed in the presence of S9 fraction: e.g., Ames test (Salmonella typhimurium TA1535, with S9) or comet assay in cultured urothelial cells to assess DNA strand breaks.
|
| Animal Protocol |
Animal/Disease Models: Male and female lacI C57BL/6 homozygous mice and male lacI Fisher 344 rats[1]
Doses: 0.05% solution in drinking water Route of Administration: Oral; for 2 weeks Experimental Results: The mutantfractions were extremely high in the bladder tissues. Bladder cancer induction is the standard model. Female or male rats/mice receive 0.05% BBN in drinking water for 8-12 weeks (or 4 mg/100 g body weight by gavage 2-3 times weekly for 12 weeks). Animals are sacrificed 20-30 weeks after initiation, and bladders are examined histologically for hyperplasia, papilloma, and carcinoma. |
| ADME/Pharmacokinetics |
BBN is a procarcinogen; its toxicokinetics involve rapid absorption from the GI tract, extensive first-pass hepatic metabolism to N-butyl-N-(3-carboxypropyl)nitrosamine (BCPN) and other metabolites, excretion in urine, and bioactivation within the bladder epithelium. Half-life is on the order of hours.
|
| Toxicity/Toxicokinetics |
BBN is highly toxic and carcinogenic. Acute toxicity: oral LD50 in rats ~1,000 mg/kg. Chronic exposure reliably induces bladder cancer. Hazard statements: H302 (harmful if swallowed), H350 (may cause cancer). It is a controlled substance requiring proper safety precautions.
|
| References | |
| Additional Infomation |
N-butyl-N-(4-hydroxybutyl)nitrosamine is a dark red liquid. (NTP, 1992)
N-butyl-N-(4-hydroxybutyl)nitrosamine is a nitrosamine containing butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade invasive cancer of the bladder but not cancer of other tissues. It is a carcinogen. It is a primary alcohol and nitrosamine. N-butyl-N-(4-hydroxybutyl)nitrosamine is a synthetic carcinogenic compound found in various fumes and industrial products. N-butyl-N-4-hydroxybutyl nitrosamine has been used in biomedical research to induce transitional cell carcinoma and squamous cell carcinoma of the bladder and to promote experimental liver cancer, possibly through aberrant DNA methylation. (NCI04) A substituted carcinogenic nitrosamine. BBN is exclusively a research chemical for inducing bladder cancer; it is not a therapeutic drug. It is also used in chemoprevention studies (testing agents that block BBN-induced carcinogenesis). No clinical trials or regulatory approvals exist for human use. |
| Molecular Formula |
C8H18N2O2
|
|---|---|
| Molecular Weight |
174.24
|
| Exact Mass |
174.137
|
| CAS # |
3817-11-6
|
| PubChem CID |
19665
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
1.02g/cm3
|
| Boiling Point |
320.2ºC at 760mmHg
|
| Flash Point |
147.5ºC
|
| Index of Refraction |
1.474
|
| LogP |
1.542
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
12
|
| Complexity |
109
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])N=O
|
| InChi Key |
DIKPQFXYECAYPC-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C8H18N2O2/c1-2-3-6-10(9-12)7-4-5-8-11/h11H,2-8H2,1H3
|
| Chemical Name |
N-butyl-N-(4-hydroxybutyl)nitrous amide
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.35 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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: ≥ 2.5 mg/mL (14.35 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 DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (14.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.7392 mL | 28.6961 mL | 57.3921 mL | |
| 5 mM | 1.1478 mL | 5.7392 mL | 11.4784 mL | |
| 10 mM | 0.5739 mL | 2.8696 mL | 5.7392 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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