Showing Compound Card for 2-Nitropropane (CDB000515)

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Record Information
Version1.0
Created at2020-03-19 00:41:15 UTC
Updated at2020-11-18 16:35:14 UTC
CannabisDB IDCDB000515
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Nitropropane
Description2-Nitropropane, also known as i-C3H7NO2, belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon. 2-Nitropropane is a very weakly acidic compound (based on its pKa). 2-Nitropropane is a potentially toxic compound. It is a secondary nitroalkane with propane being the carbon backbone, on which a hydrogen at position 2 has been replaced by a nitro group. 2-Nitropropane is a colorless liquid and it is used a solvent. 2-Nitropropane is produced by the high-temperature vapor-phase nitration of propane and usually contains 1-nitropropane as an impurity. 2-Nitropropane is also produced as a volatile by-product that can be captured during Leonard's ring-closure hydantoin preparation. 2-Nitropropane is used as a solvent or additive in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings. It is also used as a feedstock for other industrial chemicals, and in the synthesis of pharmaceuticals such as phentermine, chlorphentermine, and teclozan. It serves as an oxidant in the Hass–Bender oxidation process. 2-Nitropropane has been detected as a volatile component of seized cannabis samples (PMID: 26657499 ) and it is also a constituent of tobacco smoke (PMID: 21556207 ). Based on studies in animals, it is reasonably anticipated to be a human carcinogen (PMID: 2038276 ) and it is listed as an IARC Group 2B carcinogen.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DimethylnitromethaneChEBI
I-C3H7NO2ChEBI
IsonitropropaneChEBI
Sec-nitropropaneChEBI
Chemical FormulaC3H7NO2
Average Molecular Weight89.09
Monoisotopic Molecular Weight89.0477
IUPAC Name2-nitropropane
Traditional Nameβ-nitropropane
CAS Registry Number79-46-9
SMILES
CC(C)[N+]([O-])=O
InChI Identifier
InChI=1S/C3H7NO2/c1-3(2)4(5)6/h3H,1-2H3
InChI KeyFGLBSLMDCBOPQK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon.
KingdomOrganic compounds
Super ClassOrganic 1,3-dipolar compounds
ClassAllyl-type 1,3-dipolar organic compounds
Sub ClassOrganic nitro compounds
Direct ParentC-nitro compounds
Alternative Parents
Substituents
  • C-nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.71ALOGPS
logP0.8ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)9.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.75 m³·mol⁻¹ChemAxon
Polarizability8.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-c62d53509dc9461f2cae2014-09-20View Spectrum
Predicted GC-MS2-Nitropropane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Nitropropane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-64bea570a8bf3b8db40c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-2fbb817c7c8506267fd82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-75dd6f781ab28ae4d0892016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-9000000000-c67f074fac0e7a7803c02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-811f4921eb1de68d11162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-aa3f896a8357998727032016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0245265
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID387
KEGG Compound IDC02116
BioCyc IDCPD-244
BiGG IDNot Available
Wikipedia Link2-Nitropropane
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16037
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  2. Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A: Hazardous compounds in tobacco smoke. Int J Environ Res Public Health. 2011 Feb;8(2):613-28. doi: 10.3390/ijerph8020613. Epub 2011 Feb 23. [PubMed:21556207 ]
  3. Haas-Jobelius M, Ziegler-Skylakakis K, Andrae U: Nitroreduction is not involved in the genotoxicity of 2-nitropropane in cultured mammalian cells. Mutagenesis. 1991 Jan;6(1):87-91. doi: 10.1093/mutage/6.1.87. [PubMed:2038276 ]