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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:56 UTC
Update Date2019-01-11 19:42:31 UTC
HMDB IDHMDB0031404
Secondary Accession Numbers
  • HMDB31404
Metabolite Identification
Common NameCyclohexylamine
DescriptionCyclohexylamine is a food contaminant arising from its use as a boiler water additive Cyclohexylamine, also called hexahydroaniline, 1-aminocyclohexane, or aminohexahydrobenzene, is an organic chemical, an amine derived from cyclohexane. It is a clear to yellowish liquid with fishy odor, with melting point of 17.7 °C and boiling point 134.5 °C, miscible with water. Like other amines, it is of mildly alkaline nature, compared to strong bases such as NaOH, but it is a stronger base than its aromatic sister compound aniline, which differs only in that its ring is aromatic. It is flammable, with flash point at 28.6 °C. Explosive mixtures with air can be formed above 26 °C. It is toxic by both ingestion and inhalation; the inhalation itself may be fatal. It readily absorbs through skin, which it irritates. It is corrosive. Cyclohexylamine is listed as an extremely hazardous substance as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act
Structure
Data?1547235751
Synonyms
ValueSource
CyclohexanamineChEBI
1-amino-CYCLOHEXANEHMDB
1-AminocyclohexaneHMDB
1-CyclohexylamineHMDB
AminocyclohexaneHMDB
AminocylcohexaneHMDB
AminohexahydrobenzeneHMDB
CHAHMDB
Cyclohexanamine, 9ciHMDB
Cyclohexyl amineHMDB
Cyclohexylamine.HCLHMDB
HAIHMDB
hexahydro-AnilineHMDB
hexahydro-BenzenamineHMDB
HexahydroanilineHMDB
HexahydrobenzenamineHMDB
CyclohexylaminesMeSH
Chemical FormulaC6H13N
Average Molecular Weight99.1741
Monoisotopic Molecular Weight99.104799421
IUPAC Namecyclohexanamine
Traditional Namecyclohexylamine
CAS Registry Number108-91-8
SMILES
NC1CCCCC1
InChI Identifier
InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
InChI KeyPAFZNILMFXTMIY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclohexylamines. These are organic compounds containing a cyclohexylamine moiety, which consist of a cyclohexane ring attached to an amine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassCyclohexylamines
Direct ParentCyclohexylamines
Alternative Parents
Substituents
  • Cyclohexylamine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-18 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP1.49Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.82 g/LALOGPS
logP1.3ALOGPS
logP1.17ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)10.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.93 m³·mol⁻¹ChemAxon
Polarizability12.44 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-9f0030286662e0b15eb9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-4111cb4650bbc40fe3f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0940000000-63acc27993274132e19fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-9f0030286662e0b15eb9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-4111cb4650bbc40fe3f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0940000000-63acc27993274132e19fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7i-9000000000-2251611ad13a6a9864a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-07bc7f7b29f19ae75ff1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-c6ee7d94daa20970cbe2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-279ecb6c063cc263eddcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-0ee49feae71797bbfabfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4u-9000000000-9e995786680410021ca7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-9200000000-784fd5e818b551146b97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-5900000000-a13e46624e186ef48e40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9700000000-2f046d7c96551ced376fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-6a969aff90392ba70200View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-f3599eae069cb694be4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-6f77653ebb216d6e5504View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001m-9000000000-4f9602f5225c66054873View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003478
KNApSAcK IDC00044142
Chemspider ID7677
KEGG Compound IDC00571
BioCyc IDCPD-303
BiGG IDNot Available
Wikipedia LinkCyclohexylamine
METLIN IDNot Available
PubChem Compound7965
PDB IDNot Available
ChEBI ID15773
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .