DICYCLOHEXYLAMINE

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 Search

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

Description
Sources: http://www.mpbio.com/detailed_info.php?family_key=02150877&country=176
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
spermidine biosynthetic process 1 Target ID: GO:0008295 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11728024	Inhibitor 8297		97.0 µM [IC50]
Spermidine synthase 2 Target ID: CHEMBL2429 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7409140	Inhibitor 8297		0.2 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium falciparum malaria 63 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11728024	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Spermidine is essential for normal proliferation of trypanosomatid protozoa.	2001 Nov 23	11728444
Role of hyperforin in the antidepressant-like activity of Hypericum perforatum extracts.	2002 Dec	12457273
Selectivity of lithium electrodes: correlation with ion-lonophore complex stability constants and with interfacial exchange current densities.	2002 Feb 1	11838669
[Binding of dicyclohexylamide derivatives of N-substituted aminocarboxylic acids with muscarinic cholinoreceptors and beta-adrenoreceptors].	2002 Sep-Oct	12596513
Effects of peripheral CCK receptor blockade on gastric emptying in rats.	2003 Jan	12388446
Major intermediates in organophosphate synthesis (PCl3, POCl3, PSCl3, and their diethyl esters) are anticholinesterase agents directly or on activation.	2003 Mar	12641435
In vitro effects of the dicyclohexylammonium salt of hyperforin on interleukin-6 release in different experimental models.	2004 Jul	15303261
Abdominal vagal mediation of the satiety effects of CCK in rats.	2004 Jun	14701717
Hyperforin inhibits cancer invasion and metastasis.	2004 Sep 1	15342408
4-Methylideneisoxazolidin-5-ones--a new class of alpha-methylidene-gamma-lactones with high cytostatic activity.	2006 Mar 1	16314098
Diastereoselective arylithium addition to an alpha-trifluoromethyl imine. Practical synthesis of a potent cathepsin K inhibitor.	2006 May 26	16709080
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Hyperforin blocks neutrophil activation of matrix metalloproteinase-9, motility and recruitment, and restrains inflammation-triggered angiogenesis and lung fibrosis.	2007 May	17289834
A concise synthesis of (S)-N-ethoxycarbonyl-alpha-methylvaline.	2007 Sep 14	17713956
Dicyclo-hexyl-ammonium thio-cyanate.	2008 Jan 4	21201398
Dicyclo-hexyl-ammonium bromide.	2008 Jul 31	21203314
1,3-Dicyclo-hexyl-1-isonicotinoylurea monohydrate.	2008 Jul 9	21203166
Spectrophotometric determination of cyclotrimethylenetrinitramine (RDX) in explosive mixtures and residues with the Berthelot reaction.	2008 Mar 31	18331858
2-(4-Morpholine-carbothio-ylsulfan-yl)-acetic acid.	2010 Apr 14	21579132
Uranium(IV) amide and halide derivatives of two tripodal tris(N-arylamido-dimethylsilyl)methanes.	2010 Aug 7	20631947
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 Jan 15	20006100
The dicyclo-hexyl-amine salt of RG108 (N-phthalyl-l-tryptophan), a potential epigenetic modulator.	2010 Nov 13	21589471
Dicyclo-hexyl-ammonium 3-[(hy-droxy-meth-yl)carbamo-yl]propano-ate.	2010 Nov 6	21589403

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

Name

Type

Language

DICYCLOHEXYLAMINE

Systematic Name

English

NSC-3399

Code

English

DICYCLOHEXYLAMINE [HSDB]

Common Name

English

DICYCLOHEXYLAMINE [MI]

Common Name

English

Code System Code Type Description

MESH

C011769