U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H23N
Molecular Weight 181.3177
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DICYCLOHEXYLAMINE

SMILES

C1CCC(CC1)NC2CCCCC2

InChI

InChIKey=XBPCUCUWBYBCDP-UHFFFAOYSA-N
InChI=1S/C12H23N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h11-13H,1-10H2

HIDE SMILES / InChI
Molecular Formula C12H23N
Molecular Weight 181.3177
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/6508744

Dicyclohexylamine is an inhibitor of bacterial and mammalian spermidine synthase, an inhibitor of aminopropyltransferases, promotes ornithine decarboxylase activity possibly by the inhibition of spermidine biosynthesis. A possible antifungal agent in combination with 2,4,5-triochlorophenol.

CNS Activity

CNS Penetrant
2554
Curator's Comment: The intraperitoneally injected Dicyclohexylamine was shown to cross the blood-brain barrier easily in rats

Originator

Bayer
156
Curator's Comment: Dicyclohexylamine has been known in the laboratory since 1893, when A. Baeyer reduced cyclohexanone oxime in absolute alcohol solution to cyclohexylamine by means of metallic sodium. # Bayer A

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 97.0 µM [IC50]
Inhibitor
8297
 0.2 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Epithelial-mesenchymal interactions and lung branching morphogenesis. Role of polyamines and transforming growth factor beta1.
2001
Genotoxic effects of N-nitrosodicyclohexylamine in isolated human lymphocytes.
2001 Apr
Multivariate curve resolution of wavelet and Fourier compressed spectra.
2001 Jul 15
Spermidine is essential for normal proliferation of trypanosomatid protozoa.
2001 Nov 23
A new route to hindered tertiary amines.
2001 Oct 5
Role of hyperforin in the antidepressant-like activity of Hypericum perforatum extracts.
2002 Dec
[Binding of dicyclohexylamide derivatives of N-substituted aminocarboxylic acids with muscarinic cholinoreceptors and beta-adrenoreceptors].
2002 Sep-Oct
Effects of peripheral CCK receptor blockade on food intake in rats.
2003 Aug
Effects of peripheral CCK receptor blockade on feeding responses to duodenal nutrient infusions in rats.
2003 Feb
Major intermediates in organophosphate synthesis (PCl3, POCl3, PSCl3, and their diethyl esters) are anticholinesterase agents directly or on activation.
2003 Mar
Molecular design of functional peptides by utilizing unnatural amino acids: toward artificial and photofunctional protein.
2004
Inclusion complexes of 2-chloroethylnitrososulfamides (CENS) with beta-cyclodextrin.
2004 Jan
In vitro effects of the dicyclohexylammonium salt of hyperforin on interleukin-6 release in different experimental models.
2004 Jul
Induction of hyperammonia in irradiated hepatoma cells: a recapitulation and possible explanation of the phenomenon.
2004 Jul 5
Abdominal vagal mediation of the satiety effects of CCK in rats.
2004 Jun
Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions.
2004 Jun 25
Structure-property correlation of a new family of organogelators based on organic salts and their selective gelation of oil from oil/water mixtures.
2004 Oct 25
Determination of volatile corrosion inhibitors by capillary electrophoresis.
2004 Oct 8
The efficacy of inhibitors involved in spermidine metabolism in Plasmodium falciparum, Anopheles stephensi and Trypanosoma evansi.
2004 Sep
Hyperforin inhibits cancer invasion and metastasis.
2004 Sep 1
Diastereoselective arylithium addition to an alpha-trifluoromethyl imine. Practical synthesis of a potent cathepsin K inhibitor.
2006 May 26
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Dicyclo-hexyl-ammonium bis-(chloro-difluoro-acetato-κO)cyclo-pentyl-diphenyl-stannate(IV).
2008 Apr 23
Dicyclo-hexyl-ammonium bis-(chloro-difluoro-acetato-κO)cyclo-hexyl-diphenyl-stannate(IV).
2008 Apr 26
Dicyclo-hexyl-ammonium thio-cyanate.
2008 Jan 4
Dicyclo-hexyl-ammonium bromide.
2008 Jul 31
1,3-Dicyclo-hexyl-1-isonicotinoylurea monohydrate.
2008 Jul 9
Retention time prediction of compounds in Grob standard mixture for apolar capillary columns in temperature-programmed gas chromatography.
2009 Jan
Plasmodium falciparum spermidine synthase inhibition results in unique perturbation-specific effects observed on transcript, protein and metabolite levels.
2010 Apr 12
2-(4-Morpholine-carbothio-ylsulfan-yl)-acetic acid.
2010 Apr 14
Uranium(IV) amide and halide derivatives of two tripodal tris(N-arylamido-dimethylsilyl)methanes.
2010 Aug 7
Direct observation of various reaction pathways of arylnitrenes in different crystal environments caused by acid-base complex formation.
2010 Dec
The dicyclo-hexyl-amine salt of RG108 (N-phthalyl-l-tryptophan), a potential epigenetic modulator.
2010 Nov 13
Dicyclo-hexyl-ammonium 3-[(hy-droxy-meth-yl)carbamo-yl]propano-ate.
2010 Nov 6
Patents

Patents

03985740
1
04139701
1
04140694
1
04237129
1
04242265
8
04661512
2
04740600
4
04772753
1
04904791
1
05032609
1
05173289
1
05639775
1
05663350
1
06764840
2
07115619
2
07323448
2
07541020
1
07728176
3
07763731
4
07999114
1
08263634
2
08268990
2
08343955
6
08362073
1
08445530
1
08455530
1
08637562
1
08674111
28
08802720
1
JP2002138293A
1
JP2003300944A
1
JP2004534059A
5
JP2011500893A
6
JPH03257013A
1
JPH05286927A
1
JPH0592139A
1
JPS5638373A
1
JPS59219290A
1
JPS6281494A
4
JPS63201190A
1
JPS6474296A
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
100 uM-200 uM of Dicyclohexylamine decreased P. falciparum strain NF54 parasitemias to 0% within 72 hours
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:37:58 GMT 2023
Edited
by admin
on Fri Dec 15 19:37:58 GMT 2023
Record UNII
1A93RJW924
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DICYCLOHEXYLAMINE
HSDB   MI  
Systematic Name English
NSC-3399
Code English
DICYCLOHEXYLAMINE [HSDB]
Common Name English
DICYCLOHEXYLAMINE [MI]
Common Name English
Code System Code Type Description
MESH
C011769
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
HSDB
4018
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-980-7
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
PUBCHEM
7582
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
CAS
101-83-7
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
NSC
3399
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
MERCK INDEX
m4376
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY Merck Index
FDA UNII
1A93RJW924
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID6025018
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
WIKIPEDIA
Dicyclohexylamine
Created by admin on Fri Dec 15 19:37:58 GMT 2023 , Edited by admin on Fri Dec 15 19:37:58 GMT 2023
PRIMARY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966