n-Nitrosodi-n-propylamine (T3D0112)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-03-06 18:58:06 UTC
Update Date2014-12-24 20:21:08 UTC
Accession NumberT3D0112
Identification
Common Namen-Nitrosodi-n-propylamine
ClassSmall Molecule
DescriptionN-Nitrosodi-n-propylamine is a chemical produced by industry in small amounts for research. Small amounts of n-nitrosodi-n-propylamine are also produced as a side reaction during some manufacturing processes, as a contaminant in some weed killers, and during the manufacture of some rubber products. It is one ingredient of cigarette. (5)
Compound Type
  • Amine
  • Cigarette Toxin
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-Oxo-1,1-dipropylhydrazine
Di-N-propylnitrosamine
Di-N-propylnitrosoamine
Dipropylnitrosamine
N,N-di-N-propylnitrosamine
N,N-dipropylnitrosamine
N-nitroso di-N-propylamine
N-nitroso(di-N-propyl)amine
N-nitroso-N-dipropylamine
N-Nitroso-N-propyl-1-propanamine
N-nitroso-N-propylpropan-1-amine
N-Nitrosodi-N-propylamine
N-nitrosodi-N-propylamine
N-nitrosodipropylamine
Nitrosodipropylamine
Nitrous dipropylamide
Chemical FormulaC6H14N2O
Average Molecular Mass130.188 g/mol
Monoisotopic Mass130.111 g/mol
CAS Registry Number621-64-7
IUPAC Namenitrosodipropylamine
Traditional NameN-nitrosodipropylamine
SMILESCCCN(CCC)N=O
InChI IdentifierInChI=1S/C6H14N2O/c1-3-5-8(7-9)6-4-2/h3-6H2,1-2H3
InChI KeyInChIKey=YLKFDHTUAUWZPQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic n-nitroso compounds. These are organic compounds containing a n-nitroso group -NN=O.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic nitroso compounds
Direct ParentOrganic N-nitroso compounds
Alternative Parents
Substituents
  • Organic n-nitroso compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceYellow liquid.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point206 °C
Solubility13 mg/mL at 24 °C [MIRVISH,SS et al.(1976)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.3 g/LALOGPS
logP1.57ALOGPS
logP1.8ChemAxon
logS-0.93ALOGPS
pKa (Strongest Basic)3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.6 m³·mol⁻¹ChemAxon
Polarizability15.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9200000000-7a59226c684fdfa7f3f42021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0019-9500000000-0704dc1a231c669f02cb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-000i-9200000000-154023f596f82ff606122021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0udr-9000000000-cf38c049fad6b029abf92021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-000i-9000000000-7f3e7dfc90998dac68052021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0udi-9000000000-7817e43d165c2c3db63a2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-519b13d74f5fd41dae332016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-ec2e51e590dd7bb0651d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b184a59d7647d7a9126a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-de2892f0b560af3792912016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-4900000000-24bf802b1bb215f4745f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d063bf39130b38e25ac92016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-632355cddcea307ac9e72014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
Toxicity Profile
Route of ExposureOral (5); inhalation (5) ; dermal (5).
Mechanism of ToxicityReactive metabolites of n-nitrosodi-n-propylamine are believed to form adducts with DNA, resulting in carcinogenic effects. (5)
Metabolismn-Nitrosodi-n-propylamine can be absorbed through oral, inhalation, or dermal routes. It is metabolized by cytochrome p-450 enzymes (mainly CYP 2E1) into its reactive metabolites via oxidation at the alpha, beta and gamma carbon positions. Alpha carbon oxidation is regarded as the primary pathway, resulting in formation of propionaldehyde, 1-propanol, and 2-propanol. The metabolites of n-nitrosodi-n-propylamine are excreted mainly in the urine. (5, 1)
Toxicity ValuesLD50: 480 mg/kg (Oral, Rat) (2) LD50: 487 mg/kg (Subcutaneous, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesSmall amounts of n-nitrosodi-n-propylamine are also produced as a side reaction during some manufacturing processes, as a contaminant in some weed killers, and during the manufacture of some rubber products. (5)
Minimum Risk LevelAcute Oral: 0.095 mg/kg/day (3)
Health EffectsHigh levels of n-nitrosodi-n-propylamine may damage the liver, lung, stomach, kidneys, and heart. n-Nitrosodi-n-propylamine is also a likely carcinogen. (5)
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID12130
ChEMBL IDCHEMBL166242
ChemSpider ID11632
KEGG IDC19279
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD-630
CTD IDC013161
Stitch IDn-Nitrosodi-n-propylamine
PDB IDNot Available
ACToR ID1053
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0112.pdf
General References
  1. Teiber JF, Hollenberg PF: Identification of the human liver microsomal cytochrome P450s involved in the metabolism of N-nitrosodi-n-propylamine. Carcinogenesis. 2000 Aug;21(8):1559-66. [10910959 ]
  2. IARC (1983). Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-Present. (Multivolume work).
  3. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1989). Toxicological profile for n-nitrosodi-n-propylamine. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1989). Toxicological profile for n-nitrosodi-n-propylamine. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]