4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (CHEM002944)

Record Information
Version1.0
Creation Date2014-08-29 04:48:37 UTC
Update Date2026-08-18 01:27:21 UTC
Accession NumberCHEM002944
Identification
Common Name4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
ClassSmall Molecule
Description
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol belongs to the family of Pyridines and Derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butan-1-olChEBI
4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanolChEBI
4-[Methyl(nitroso)amino]-1-(3-pyridyl)-1-butanolChEBI
4-[Methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-olChEBI
NNALChEBI
NNAL CPDHMDB
4-(Methylnitrosoamino)-1--(3-pyridyl)-1-butanolHMDB
4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)butan-1-olHMDB
MNAPB CPDHMDB
Chemical FormulaC10H15N3O2
Average Molecular Mass209.245 g/mol
Monoisotopic Mass209.116 g/mol
CAS Registry Number76014-81-8
IUPAC Name4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-ol
Traditional Name4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-ol
SMILESCN(CCCC(O)C1=CN=CC=C1)N=O
InChI IdentifierInChI=1S/C10H15N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8,10,14H,3,5,7H2,1H3
InChI KeyOGRXKBUCZFFSTL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassNot Available
Direct ParentPyridines and derivatives
Alternative Parents
Substituents
  • Pyridine
  • Heteroaromatic compound
  • Secondary alcohol
  • Organic n-nitroso compound
  • Azacycle
  • Organic nitroso compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.64 g/LALOGPS
logP0.48ALOGPS
logP0.49ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)14.23ChemAxon
pKa (Strongest Basic)4.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area65.79 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity57.98 m³·mol⁻¹ChemAxon
Polarizability22.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of Toxicity4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) is a substrate of UDP-glucuronyl transferase, leading to the formation of [4-(methylnitrosamino)-1-(3-pyridyl)but-1-yl]-b-O-D-glycopyranosiduronic acid. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0041809
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-21235
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID94646
ChEBI ID82569
PubChem Compound ID104856
Kegg Compound IDC19574
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21154658
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24521204
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24648246
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25218107
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25544129
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26595795
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26744252
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=27632782
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27834821
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29131934
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=29186507
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=29390940
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29460622
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=29475963
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=29651838
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=29739005
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=30136502
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=30714728
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=31307193
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=31470076
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=31578206
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=31833541
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=32716026
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=32944094
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=33210550
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=8634661