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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:42:56 UTC

Update Date

2023-02-21 17:20:29 UTC

HMDB ID

HMDB0031404

Secondary Accession Numbers

HMDB31404

Metabolite Identification

Common Name

Cyclohexylamine

Description

Cyclohexylamine 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cyclohexanamine	ChEBI
1-amino-CYCLOHEXANE	HMDB
1-Aminocyclohexane	HMDB
1-Cyclohexylamine	HMDB
Aminocyclohexane	HMDB
Aminocylcohexane	HMDB
Aminohexahydrobenzene	HMDB
CHA	HMDB
Cyclohexanamine, 9ci	HMDB
Cyclohexyl amine	HMDB
Cyclohexylamine.HCL	HMDB
HAI	HMDB
hexahydro-Aniline	HMDB
hexahydro-Benzenamine	HMDB
Hexahydroaniline	HMDB
Hexahydrobenzenamine	HMDB
Cyclohexylamines	MeSH, HMDB

Chemical Formula

C₆H₁₃N

Average Molecular Weight

99.1741

Monoisotopic Molecular Weight

99.104799421

IUPAC Name

cyclohexanamine

Traditional Name

cyclohexylamine

CAS Registry Number

108-91-8

SMILES

NC1CCCCC1

InChI Identifier

InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2

InChI Key

PAFZNILMFXTMIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Cyclohexylamines

Direct Parent

Cyclohexylamines

Alternative Parents

Substituents

Cyclohexylamine
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Amine
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

primary aliphatic amine (CHEBI:15773 )
a small molecule (CPD-303 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0031404)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031404)
Cytoplasm (HMDB: HMDB0031404)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0031404)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0031404)

Source

Endogenous

Endogenous (HMDB: HMDB0031404)

Exogenous

Food

Food (HMDB: HMDB0031404)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-18 °C	Not Available
Boiling Point	134.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000 mg/mL at 20 °C	Not Available
LogP	1.49	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.82 g/L	ALOGPS
logP	1.3	ALOGPS
logP	1.17	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	10.45	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.93 m³·mol⁻¹	ChemAxon
Polarizability	12.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	119.812	31661259
DarkChem	[M-H]-	113.718	31661259
DeepCCS	[M+H]+	129.666	30932474
DeepCCS	[M-H]-	127.647	30932474
DeepCCS	[M-2H]-	163.051	30932474
DeepCCS	[M+Na]+	137.592	30932474
AllCCS	[M+H]+	122.7	32859911
AllCCS	[M+H-H2O]+	117.8	32859911
AllCCS	[M+NH4]+	127.3	32859911
AllCCS	[M+Na]+	128.6	32859911
AllCCS	[M-H]-	120.4	32859911
AllCCS	[M+Na-2H]-	123.6	32859911
AllCCS	[M+HCOO]-	127.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclohexylamine	NC1CCCCC1	1191.7	Standard polar	33892256
Cyclohexylamine	NC1CCCCC1	835.4	Standard non polar	33892256
Cyclohexylamine	NC1CCCCC1	861.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclohexylamine,1TMS,isomer #1	C[Si](C)(C)NC1CCCCC1	1052.6	Semi standard non polar	33892256
Cyclohexylamine,1TMS,isomer #1	C[Si](C)(C)NC1CCCCC1	1047.1	Standard non polar	33892256
Cyclohexylamine,2TMS,isomer #1	C[Si](C)(C)N(C1CCCCC1)[Si](C)(C)C	1304.8	Semi standard non polar	33892256
Cyclohexylamine,2TMS,isomer #1	C[Si](C)(C)N(C1CCCCC1)[Si](C)(C)C	1296.5	Standard non polar	33892256
Cyclohexylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCCC1	1305.7	Semi standard non polar	33892256
Cyclohexylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCCC1	1254.2	Standard non polar	33892256
Cyclohexylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCCC1)[Si](C)(C)C(C)(C)C	1713.7	Semi standard non polar	33892256
Cyclohexylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCCC1)[Si](C)(C)C(C)(C)C	1671.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cyclohexylamine EI-B (Non-derivatized)	splash10-0a4i-9000000000-9f0030286662e0b15eb9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclohexylamine EI-B (Non-derivatized)	splash10-0a4i-9000000000-4111cb4650bbc40fe3f4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclohexylamine GC-EI-TOF (Non-derivatized)	splash10-0udi-0940000000-63acc27993274132e19f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclohexylamine EI-B (Non-derivatized)	splash10-0a4i-9000000000-9f0030286662e0b15eb9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclohexylamine EI-B (Non-derivatized)	splash10-0a4i-9000000000-4111cb4650bbc40fe3f4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclohexylamine GC-EI-TOF (Non-derivatized)	splash10-0udi-0940000000-63acc27993274132e19f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclohexylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7i-9000000000-2251611ad13a6a9864a9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclohexylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine LC-ESI-QQ , positive-QTOF	splash10-0udi-1900000000-07bc7f7b29f19ae75ff1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine LC-ESI-QQ , positive-QTOF	splash10-001i-9100000000-c6ee7d94daa20970cbe2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine LC-ESI-QQ , positive-QTOF	splash10-0a4i-9000000000-279ecb6c063cc263eddc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine LC-ESI-QQ , positive-QTOF	splash10-0a4i-9000000000-0ee49feae71797bbfabf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine LC-ESI-QQ , positive-QTOF	splash10-0a4u-9000000000-9e995786680410021ca7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine LC-ESI-QFT , positive-QTOF	splash10-001i-9200000000-784fd5e818b551146b97	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 0V, Positive-QTOF	splash10-0udi-2900000000-83bc50475e32e1dc37f4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 35V, Positive-QTOF	splash10-0a4i-9000000000-0d2e0e3482cb8de41093	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 10V, Positive-QTOF	splash10-0udi-7900000000-1e27502918a80e955ad4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 30V, Positive-QTOF	splash10-0zfu-9400000000-d80f5133631de0c361d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 10V, Positive-QTOF	splash10-053r-9100000000-79e9d24c3f37f85d7271	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 35V, Positive-QTOF	splash10-001i-9200000000-3b7fc0916b900264cf8b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 30V, Positive-QTOF	splash10-0udi-4900000000-b7c1c4e789b158ab26e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 0V, Positive-QTOF	splash10-0udi-0900000000-2fcad6de58a2ad4c68df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 10V, Positive-QTOF	splash10-0ue9-9700000000-ac86d5f2a123dcdbbe60	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 20V, Positive-QTOF	splash10-0a4i-9000000000-e1f7dea6f0513580722d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 30V, Positive-QTOF	splash10-0a4i-9000000000-850154bca79ef5f0eb1c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclohexylamine 40V, Positive-QTOF	splash10-0a4l-9000000000-8a4775d4b9df25ee27ee	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexylamine 10V, Positive-QTOF	splash10-0ue9-5900000000-a13e46624e186ef48e40	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexylamine 20V, Positive-QTOF	splash10-0ue9-9700000000-2f046d7c96551ced376f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexylamine 40V, Positive-QTOF	splash10-052f-9000000000-6a969aff90392ba70200	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexylamine 10V, Negative-QTOF	splash10-0002-9000000000-f3599eae069cb694be4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexylamine 20V, Negative-QTOF	splash10-0002-9000000000-6f77653ebb216d6e5504	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexylamine 40V, Negative-QTOF	splash10-001m-9000000000-4f9602f5225c66054873	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexylamine 10V, Negative-QTOF	splash10-0002-9000000000-9026c27716a040616792	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24713860	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	24713860	details

Associated Disorders and Diseases

Disease References

Schizophrenia
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