Clozapine, Desmethyl (CHEM045929)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:49:31 UTC
Update Date2016-11-09 01:23:26 UTC
Accession NumberCHEM045929
Identification
Common NameClozapine, Desmethyl
ClassSmall Molecule
DescriptionA dibenzodoazepine substituted with chloro and piperazino groups which is a major metabolite of clozapine; a potent and selective 5-HT2C serotonin receptor antagonist.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8-Chloro-11-(1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepineChEBI
DemethylclozapineChEBI
DesmethylclozapineChEBI
N-Desmethyl clozapineChEBI
NDMCChEBI
8-Chloro-11-piperazin-1-yl-5H-dibenzo(b,e)(1,4)diazepineMeSH
NorclozapineChEBI
Chemical FormulaC17H17ClN4
Average Molecular Mass312.797 g/mol
Monoisotopic Mass312.114 g/mol
CAS Registry Number6104-71-8
IUPAC Name6-chloro-10-(piperazin-1-yl)-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene
Traditional NameNDMC
SMILESClC1=CC=C2NC3=CC=CC=C3C(=NC2=C1)N1CCNCC1
InChI IdentifierInChI=1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2
InChI KeyJNNOSTQEZICQQP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzodiazepines. Dibenzodiazepines are compounds containing a dibenzodiazepine moiety, which consists of two benzene connected by diazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub ClassDibenzodiazepines
Direct ParentDibenzodiazepines
Alternative Parents
Substituents
  • Dibenzodiazepine
  • 1,4-benzodiazepine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Imidolactam
  • Piperazine
  • Benzenoid
  • Amidine
  • Carboxylic acid amidine
  • Secondary aliphatic amine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP3.25ALOGPS
logP3.02ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.9ChemAxon
pKa (Strongest Basic)8.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area39.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.06 m³·mol⁻¹ChemAxon
Polarizability33.58 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0016-9080000000-e5a1e856cf588ec3b2c6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-7cf412ccc6a185a32893Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0039000000-447fe506f0de08f3a236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2290000000-c1c2dd97da1db1b554a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-c0fb9c4f98b955f22ee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0019000000-2a2da1946b96480241e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9060000000-b9a39c856d2c8566d39bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-19ee5c40a0267a7c3d31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0019000000-cb30f19e8d9094be09aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r6-1091000000-16307b800b31dddedd25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-36527b79e8e0db55602bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1009000000-5ddb83e6baa29fcab0a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ai-4192000000-fda9bbc6faa449b756b5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060536
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDesmethylclozapine
Chemspider IDNot Available
ChEBI ID64050
PubChem Compound ID135409468
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20156258
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20463634
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21134422
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21658379
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21712711
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21726287
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21835172
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21855612
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21912901
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21917240
11. Ekstrom J, Godoy T, Riva A: N-Desmethylclozapine exerts dual and opposite effects on salivary secretion in the rat. Eur J Oral Sci. 2010 Feb;118(1):1-8. doi: 10.1111/j.1600-0722.2009.00696.x.
12. Couchman L, Morgan PE, Spencer EP, Flanagan RJ: Plasma clozapine, norclozapine, and the clozapine:norclozapine ratio in relation to prescribed dose and other factors: data from a therapeutic drug monitoring service, 1993-2007. Ther Drug Monit. 2010 Aug;32(4):438-47. doi: 10.1097/FTD.0b013e3181dad1fb.
13. Ertugrul A, Ozdemir H, Vural A, Dalkara T, Meltzer HY, Saka E: The influence of N-desmethylclozapine and clozapine on recognition memory and BDNF expression in hippocampus. Brain Res Bull. 2011 Feb 1;84(2):144-50. doi: 10.1016/j.brainresbull.2010.11.014. Epub 2010 Dec 4.
14. Godoy T, Riva A, Ekstrom J: Clozapine-induced salivation: interaction with N-desmethylclozapine and amisulpride in an experimental rat model. Eur J Oral Sci. 2011 Aug;119(4):275-81. doi: 10.1111/j.1600-0722.2011.00832.x.
15. Heusler P, Bruins Slot L, Tourette A, Tardif S, Cussac D: The clozapine metabolite N-desmethylclozapine displays variable activity in diverse functional assays at human dopamine D(2) and serotonin 5-HT(1)A receptors. Eur J Pharmacol. 2011 Nov 1;669(1-3):51-8. doi: 10.1016/j.ejphar.2011.07.031. Epub 2011 Aug 5.
16. Humbert-Claude M, Davenas E, Gbahou F, Vincent L, Arrang JM: Involvement of histamine receptors in the atypical antipsychotic profile of clozapine: a reassessment in vitro and in vivo. Psychopharmacology (Berl). 2012 Mar;220(1):225-41. doi: 10.1007/s00213-011-2471-5. Epub 2011 Sep 13.