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
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
| 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 |
DescriptionCurator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/6508744
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6693872
Curator's Comment: The intraperitoneally injected Dicyclohexylamine was shown to cross the blood-brain barrier easily in rats
Originator
Sources: http://pubs.acs.org/doi/abs/10.1021/ie50335a011
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0008295 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11728024 |
97.0 µM [IC50] | ||
Target ID: CHEMBL2429 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7409140 |
0.2 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11728024
100 uM-200 uM of Dicyclohexylamine decreased P. falciparum strain NF54 parasitemias to 0% within 72 hours
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 19:51:41 GMT 2025
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| Record UNII |
1A93RJW924
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| Record Status |
Validated (UNII)
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| Record Version |
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m4376
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1A93RJW924
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Dicyclohexylamine
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