MASTIC GUM (CHEM006389)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:13:07 UTC
Update Date2016-11-09 01:09:43 UTC
Accession NumberCHEM006389
Identification
Common NameMASTIC GUM
ClassSmall Molecule
DescriptionHaloperidol is a high potency first-generation (typical) antipsychotic and one of the most frequently used antipsychotic medications used worldwide. While haloperidol has demonstrated pharmacologic activity at a number of receptors in the brain, it exerts its antipsychotic effect through its strong antagonism of the dopamine receptor (mainly D2), particularly within the mesolimbic and mesocortical systems of the brain. Haloperidol is indicated for the treatment of the manifestations of several psychotic disorders including schizophrenia, acute psychosis, Tourette syndrome, and other severe behavioural states. It is also used off-label for the management of chorea associated with Huntington's disease and for the treatment of intractable hiccups as it is a potent antiemetic. Dopamine-antagonizing medications such as haloperidol are though to improve psychotic symptoms and states that are caused by an over-production of dopamine, such as schizophrenia, which is theorized to be caused by a hyperdopaminergic state within the limbic system of the brain. Use of the first-generation antipsychotics (including haloperidol) is considered highly effective for the management of the "positive" symptoms of schizophrenia including hallucinations, hearing voices, aggression/hostility, disorganized speech, and psychomotor agitation. However, this class of drugs is also limited by the development of movement disorders induced by dopamine-blockade such as drug-induced parkinsonism, akathisia, dystonia, tardive dyskinesia, as well as other side effects including sedation, weight gain, and prolactin changes. While there are limited high-quality studies comparing haloperidol to lower-potency first-generation antipsychotics such as , , , and , haloperidol typically demonstrates the least amount of side effects within this class, but demonstrates a stronger disposition for causing extrapyramidal symptoms (EPS). These other low‐potency antipsychotics are limited by their lower affinity for dopamine receptors, which requires a higher dose to effectively treat symptoms of schizophrenia. In addition, they block many receptors other than the primary target (dopamine receptors), such as cholinergic or histaminergic receptors, resulting in a higher incidence of side effects such as sedation, weight gain, and hypotension. Interestingly, in vivo pharmacogenetic studies have demonstrated that the metabolism of haloperidol may be modulated by genetically determined polymorphic _CYP2D6_ activity. However, these findings contradict the findings from studies in vitro with human liver microsomes and from drug interaction studies in vivo. Inter-ethnic and pharmacogenetic differences in haloperidol metabolism may possibly explain these observations. First-generation antipsychotic drugs have largely been replaced with second- and third-generation (atypical) antipsychotics such as , , , , , and . However, haloperidol use remains widespread and is considered the benchmark for comparison in trials of the newer generation antipsychotics. The efficacy of haloperidol was first established in controlled trials in the 1960s.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(3-p-Fluorobenzoylpropyl)-4-p-chlorophenyl-4-hydroxypiperidineChEBI
4'-Fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)butyrophenoneChEBI
4'-Fluoro-4-(4-hydroxy-4-(4'-chlorophenyl)piperidino)butyrophenoneChEBI
4-(4-(Para-chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenoneChEBI
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-oneChEBI
gamma-(4-(p-Chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenoneChEBI
HaldolChEBI
HaloperidolumChEBI
g-(4-(p-Chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenoneGenerator
Γ-(4-(p-chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenoneGenerator
Chemical FormulaC21H23ClFNO2
Average Molecular Mass375.864 g/mol
Monoisotopic Mass375.140 g/mol
CAS Registry Number61789-92-2
IUPAC Name4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
Traditional Namehaloperidol
SMILESOC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1
InChI IdentifierInChI=1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2
InChI KeyLNEPOXFFQSENCJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenylpiperidine
  • Butyrophenone
  • Phenylbutylamine
  • Benzoyl
  • Aryl alkyl ketone
  • Aralkylamine
  • Chlorobenzene
  • Fluorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Gamma-aminoketone
  • Benzenoid
  • Piperidine
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.0045 g/LALOGPS
logP3.7ALOGPS
logP3.66ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.96ChemAxon
pKa (Strongest Basic)8.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability39.15 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3941000000-d115a40817bca84c859aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5941100000-c3840be760880e2d998aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0009000000-cdfdd91dd85d2c1cbd3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00or-0409000000-d542c35143556b83b87aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-3985dded029c89448ebeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-0900000000-720c0a4f1130b4237f32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-772a799ebb3b949cef0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0009000000-21c8918254235e561129Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0904000000-8c97cb39f9680dd91378Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01b9-0900000000-571a03ebb5faa3e5cd63Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-62e233fd691121c78e96Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-91bf80d34ef94ed709f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-46ef29917220709863a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-3900000000-26f391756d439f7dbfc8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00b9-9600000000-404fc399b40cfb560a99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00b9-9100000000-8779758823471091566aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-1619000000-27aa28ad7f91429f5ae7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0609000000-f7c623630d33dbd89e2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01b9-3911000000-78d5b34044714e81aec3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0904000000-de8db1cf24411de5c68bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0409000000-36213f9899b1353ed71aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-f62434729be0d8a2076fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-01b9-0900000000-dd043e9fd6bc62fc3818Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-004i-0009000000-4ad6f236f984048d7bf4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-e7a27e7c12d8389ace5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-01b9-0900000000-650121cf1e6e20a77086Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00di-0900000000-1399579b037f5be1e43dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0079-3290000000-cc6a990404ba7b9452a8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDDB00502
HMDB IDHMDB0014645
FooDB IDFDB009770
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHaloperidol
Chemspider ID3438
ChEBI ID5613
PubChem Compound ID3559
Kegg Compound IDC01814
YMDB IDNot Available
ECMDB IDM2MDB005655
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Niemegeers CJ, Laduron PM: Pharmacology and biochemistry of haloperidol. Proc R Soc Med. 1976;69 suppl 1:3-8.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10628896
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11304647
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25007358
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6725621
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=7602118