1-nitrosopyrrolidine

• ChemBase ID: 155784
• Molecular Formular: C4H8N2O
• Molecular Mass: 100.11912
• Monoisotopic Mass: 100.06366289
• SMILES: C1CCN(C1)N=O
• Canonical SMILES: O=NN1CCCC1
• InChI: InChI=1S/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2
• InChIKey: WNYADZVDBIBLJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-nitrosopyrrolidine
• IUPAC Traditional name: N-nitrosopyrrolidine
• Synonyms: N-Nitrosopyrrolidine; NPYR; 1-Nitrosopyrrolidine; NSC 18797; 1-Nitrosopyrrolidine

Database IDs

• CAS Number: 930-55-2
• EC Number: 213-218-8
• MDL Number: MFCD00003166
• PubChem SID: 162249922; 24849726
• PubChem CID: 13591

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.4439237
• LogD (pH = 7.4): 0.4444051
• Log P: 0.44441128
• Molar Refractivity: 27.5915 cm^3
• Polarizability: 9.874824 Å^3
• Polar Surface Area: 32.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Light-Yellow Oil
• Boiling Point: 214 °C(lit.)
• Flash Point: 208.4 °F; 98 °C
• Density: 1.085 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.489(lit.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: UY1575000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C4H8N2O

DETAILS

Sigma Aldrich - 158240

Biochem/physiol Actions
Induces hepatocellular carcinomas and lung adenomas in mice. Forms DNA adducts that primarily result in A:T to G:C mutations.
Packaging
10 g in glass bottle
Application
1-Nitrosopyrrolidine can be used to study carcinogens and cancer. Metabolism of nitrosamines in vivo has been tested in rats.1-Nitrosopyrrolidine has been used in a study to assess nitric oxide and spontaneous motility in chick embryos.

Toronto Research Chemicals - N545950

One of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis, but the toxicological mechanisms involved have not been elucidated.

REFERENCES

• Singer, S., et al.: J. Med. Chem., 28, 1088 (1985)
• Tomatis, L., et al.: Carcinogenesis, 18, 97 (1985)
• Helguera, A., et al.: Toxicol. Appl. Pharmacol., 221, 189 (1985)