Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H30N2.ClH |
Molecular Weight | 370.959 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)[C@](CCCN(C)CCC1=CC=CC=C1)(C#N)C2=CC=CC=C2
InChI
InChIKey=OBAQQQOVZUCKMH-BQAIUKQQSA-N
InChI=1S/C23H30N2.ClH/c1-20(2)23(19-24,22-13-8-5-9-14-22)16-10-17-25(3)18-15-21-11-6-4-7-12-21;/h4-9,11-14,20H,10,15-18H2,1-3H3;1H/t23-;/m0./s1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C23H30N2 |
Molecular Weight | 334.4977 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Levemopamil is a novel compound of the phenylalkylamine class of calcium channel blockers, possesses exceptionally high blood-brain barrier penetrability characteristics. It has a potent antagonistic action on serotonin 5-HT2-receptors. Activation of these receptors stimulates inositol phospholipid hydrolysis that can lead to the release of Ca2+ from intracellular stores as well as protein kinase C activation. Levemopamil thus has the potential for blocking deleterious increases of intracellular calcium arising from both intracellular stores and from the extracellular space. Levemopamil reduce both infarct size and extent of neuronal injury following permanent focal or transient global ischemia. The acute effect of bilateral clamping of carotid arteries on local cerebral blood flow was measured in the presence and absence of levemopamil in a separate group of rats. The data suggest that pretreatment with levemopamil reduces impairment in spatial behaviour and that this effect seems not related to the compound's cerebral vasodilatory action, but to direct neuronal mechanisms.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Postischemic (S)-emopamil therapy ameliorates focal ischemic brain injury in rats. | 1991 Mar |
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Mouse Tdho abnormality results from double point mutations of the emopamil binding protein gene (Ebp). | 2001 Aug |
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Cholesterol biosynthesis from lanosterol: molecular cloning, chromosomal localization, functional expression and liver-specific gene regulation of rat sterol delta8-isomerase, a cholesterogenic enzyme with multiple functions. | 2001 Feb 1 |
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Practical synthesis of chiral emopamil left hand as a bioactive motif. | 2002 Aug 23 |
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Gas chromatography-mass spectrometry and molecular genetic studies in families with the Conradi-Hünermann-Happle syndrome. | 2002 May |
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Purification, characterization and catalytic properties of human sterol 8-isomerase. | 2002 Nov 1 |
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Characterization of mutations in 22 females with X-linked dominant chondrodysplasia punctata (Happle syndrome). | 2002 Nov-Dec |
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Isolation of differentially expressed genes in NPM-ALK-positive anaplastic large cell lymphoma. | 2002 Sep |
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X-linked dominant chondrodysplasia punctata (CDPX2) caused by single gene mosaicism in a male. | 2003 Jan 30 |
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Molecular, biochemical, and phenotypic analysis of a hemizygous male with a severe atypical phenotype for X-linked dominant Conradi-Hunermann-Happle syndrome and a mutation in EBP. | 2003 Jan 30 |
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Discovery of novel neuronal voltage-dependent calcium channel blockers based on emopamil left hand as a bioactive template. | 2003 Mar 10 |
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Molecular prenatal diagnosis in a case of an X-linked dominant chondrodysplasia punctata. | 2003 Sep |
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Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening. | 2005 Jul 28 |
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Investigation of the phenylalkylamine binding site in hKv1.3 (H399T), a mutant with a reduced C-type inactivated state. | 2005 Oct |
|
Short-term arginine deprivation results in large-scale modulation of hepatic gene expression in both normal and tumor cells: microarray bioinformatic analysis. | 2006 Sep 8 |
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B-Type natriuretic peptide inhibited angiotensin II-stimulated cholesterol biosynthesis, cholesterol transfer, and steroidogenesis in primary human adrenocortical cells. | 2007 Aug |
|
Loss of Parp-1 affects gene expression profile in a genome-wide manner in ES cells and liver cells. | 2007 Feb 7 |
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Functional analysis of cholesterol biosynthesis by RNA interference. | 2007 May |
|
Reduced penetrance in a family with X-linked dominant chondrodysplasia punctata. | 2007 Sep-Oct |
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A Botrytis cinerea emopamil binding domain protein, required for full virulence, belongs to a eukaryotic superfamily which has expanded in euascomycetes. | 2008 Feb |
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Prenatal testing for a novel EBP missense mutation causing X-linked dominant chondrodysplasia punctata. | 2008 May |
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Anticipation in familial lattice corneal dystrophy type I with R124C mutation in the TGFBI (BIGH3) gene. | 2008 May 7 |
|
Do sex steroids exert sex-specific and/or opposite effects on gene expression in lacrimal and meibomian glands? | 2009 Aug 10 |
|
Identifying components of the hair-cell interactome involved in cochlear amplification. | 2009 Mar 25 |
|
Transcriptional profiling of rats subjected to gestational undernourishment: implications for the developmental variations in metabolic traits. | 2009 Sep 29 |
|
Gene expression profiling and network analysis reveals lipid and steroid metabolism to be the most favored by TNFalpha in HepG2 cells. | 2010 Feb 4 |
|
A novel X-linked multiple congenital anomaly syndrome associated with an EBP mutation. | 2010 Nov |
|
Conradi-Hünermann-Happle syndrome. | 2010 Nov 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8586975
Curator's Comment: Cats data
4 mg/kg/h for 15 min and then at 0.6 mg/kg/h
Route of Administration:
Intravenous
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 13:27:46 GMT 2023
by
admin
on
Sat Dec 16 13:27:46 GMT 2023
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Record UNII |
8PZ0RTT0S1
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Record Status |
Validated (UNII)
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Record Version |
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180949
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DTXSID00143805
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101238-54-4
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admin on Sat Dec 16 13:27:46 GMT 2023 , Edited by admin on Sat Dec 16 13:27:46 GMT 2023
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Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |