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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

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

Originator

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

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Direct observation of various reaction pathways of arylnitrenes in different crystal environments caused by acid-base complex formation.
2010-12
The dicyclo-hexyl-amine salt of RG108 (N-phthalyl-l-tryptophan), a potential epigenetic modulator.
2010-11-13
Dicyclo-hexyl-ammonium 3-[(hy-droxy-meth-yl)carbamo-yl]propano-ate.
2010-11-06
Uranium(IV) amide and halide derivatives of two tripodal tris(N-arylamido-dimethylsilyl)methanes.
2010-08-07
2-(4-Morpholine-carbothio-ylsulfan-yl)-acetic acid.
2010-04-14
Plasmodium falciparum spermidine synthase inhibition results in unique perturbation-specific effects observed on transcript, protein and metabolite levels.
2010-04-12
Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization.
2010-03-19
A sensitive and selective method for determination of gold(III) based on electrothermal atomic absorption spectrometry in combination with dispersive liquid-liquid microextraction using dicyclohexylamine.
2010-01-15
Selective spectrophotometric determination of TNT using a dicyclohexylamine-based colorimetric sensor.
2009-05-15
Membrane bioreactor treatment of a simulated metalworking fluid wastewater containing ethylenediaminetetraacetic acid and dicyclohexylamine.
2009-04
Retention time prediction of compounds in Grob standard mixture for apolar capillary columns in temperature-programmed gas chromatography.
2009-01
Dicyclo-hexyl-ammonium bromide.
2008-07-31
1,3-Dicyclo-hexyl-1-isonicotinoylurea monohydrate.
2008-07-09
Dicyclo-hexyl-ammonium bis-(chloro-difluoro-acetato-κO)cyclo-hexyl-diphenyl-stannate(IV).
2008-04-26
Dicyclo-hexyl-ammonium bis-(chloro-difluoro-acetato-κO)cyclo-pentyl-diphenyl-stannate(IV).
2008-04-23
Dicyclo-hexyl-ammonium 2-methoxy-benzoate.
2008-04-02
Spectrophotometric determination of cyclotrimethylenetrinitramine (RDX) in explosive mixtures and residues with the Berthelot reaction.
2008-03-31
Dicyclo-hexyl-ammonium thio-cyanate.
2008-01-04
Dimerization and isomerization reactions of alpha-lithiated terminal aziridines.
2007-12-21
A concise synthesis of (S)-N-ethoxycarbonyl-alpha-methylvaline.
2007-09-14
Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L.
2007-05
Hyperforin blocks neutrophil activation of matrix metalloproteinase-9, motility and recruitment, and restrains inflammation-triggered angiogenesis and lung fibrosis.
2007-05
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Diastereoselective arylithium addition to an alpha-trifluoromethyl imine. Practical synthesis of a potent cathepsin K inhibitor.
2006-05-26
4-Methylideneisoxazolidin-5-ones--a new class of alpha-methylidene-gamma-lactones with high cytostatic activity.
2006-03-01
Structure-property correlation of a new family of organogelators based on organic salts and their selective gelation of oil from oil/water mixtures.
2004-10-25
Determination of volatile corrosion inhibitors by capillary electrophoresis.
2004-10-08
Hyperforin inhibits cancer invasion and metastasis.
2004-09-01
The efficacy of inhibitors involved in spermidine metabolism in Plasmodium falciparum, Anopheles stephensi and Trypanosoma evansi.
2004-09
Induction of hyperammonia in irradiated hepatoma cells: a recapitulation and possible explanation of the phenomenon.
2004-07-05
In vitro effects of the dicyclohexylammonium salt of hyperforin on interleukin-6 release in different experimental models.
2004-07
Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions.
2004-06-25
Abdominal vagal mediation of the satiety effects of CCK in rats.
2004-06
[Analysis of aniline and other impurities in dicyclohexylamine products by GC and GC-MS].
2004-01
Inclusion complexes of 2-chloroethylnitrososulfamides (CENS) with beta-cyclodextrin.
2004-01
Molecular design of functional peptides by utilizing unnatural amino acids: toward artificial and photofunctional protein.
2004
Effects of peripheral CCK receptor blockade on food intake in rats.
2003-08
Major intermediates in organophosphate synthesis (PCl3, POCl3, PSCl3, and their diethyl esters) are anticholinesterase agents directly or on activation.
2003-03
[Binding of dicyclohexylamide derivatives of N-substituted aminocarboxylic acids with muscarinic cholinoreceptors and beta-adrenoreceptors].
2003-02-25
Effects of peripheral CCK receptor blockade on feeding responses to duodenal nutrient infusions in rats.
2003-02
Effects of peripheral CCK receptor blockade on gastric emptying in rats.
2003-01
Role of hyperforin in the antidepressant-like activity of Hypericum perforatum extracts.
2002-12
Ferrocene-1,1'-dicarboxylic acid as a building block in supramolecular chemistry: supramolecular structures in one, two and three dimensions.
2002-10
Selectivity of lithium electrodes: correlation with ion-lonophore complex stability constants and with interfacial exchange current densities.
2002-02-01
Genotoxicity of N-nitrosodicyclohexylamine in V79 cells in the sister chromatid exchange test and the single cell gel assay.
2001-12
Spermidine is essential for normal proliferation of trypanosomatid protozoa.
2001-11-23
Effect of drugs inhibiting spermidine biosynthesis and metabolism on the in vitro development of Plasmodium falciparum.
2001-11
A new route to hindered tertiary amines.
2001-10-05
Multivariate curve resolution of wavelet and Fourier compressed spectra.
2001-07-15
Epithelial-mesenchymal interactions and lung branching morphogenesis. Role of polyamines and transforming growth factor beta1.
2001
Patents

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 Mon Mar 31 19:51:41 GMT 2025
Edited
by admin
on Mon Mar 31 19:51:41 GMT 2025
Record UNII
1A93RJW924
Record Status Validated (UNII)
Record Version
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Name Type Language
Dicyclohexylamine
HSDB   MI  
Systematic Name English
NSC-3399
Preferred Name English
DICYCLOHEXYLAMINE [HSDB]
Common Name English
DICYCLOHEXYLAMINE [MI]
Common Name English
Code System Code Type Description
MESH
C011769
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
HSDB
4018
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-980-7
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
PUBCHEM
7582
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
CAS
101-83-7
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
NSC
3399
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
MERCK INDEX
m4376
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY Merck Index
FDA UNII
1A93RJW924
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID6025018
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY
WIKIPEDIA
Dicyclohexylamine
Created by admin on Mon Mar 31 19:51:41 GMT 2025 , Edited by admin on Mon Mar 31 19:51:41 GMT 2025
PRIMARY