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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015546
Secondary Accession Numbers
  • HMDB15546
Metabolite Identification
Common NamePropericiazine
DescriptionPropericiazine, also known as piperocyanomazine or neuleptil, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. Propericiazine is a drug which is used for use as adjunctive medication in some psychotic patients. propericiazine (pericyazine)is used for the control of residual prevailing hostility, impulsiveness and aggressiveness. . The primary uses of periciazine include in the short-term treatment of severe anxiety or tension and in the maintenance treatment of psychotic disorders such as schizophrenia. Propericiazine is a very strong basic compound (based on its pKa). Periciazine is a rather sedating and anticholinergic antipsychotic, and despite being classed with the typical antipsychotics, its risk of extrapyramidal side effects is comparatively low. It is commonly sold in Canada and Russia under the tradename Neuleptil and in United Kingdom and Australia under the tradename Neulactil. Periciazine is not approved for sale in the United States. It has a relatively high risk of causing hyperprolactinaemia and a moderate risk of causing weight gain and orthostatic hypotension. There is insufficient evidence to determine whether periciazine is more or less effective than other antipsychotics. A 2014 systematic review compared periciazine with typical antipsychotics for schizophrenia:Periciazine has also been studied in the treatment of opioid dependence.
Structure
Data?1582753308
Synonyms
ValueSource
10-(3-(4-Hydroxypiperidino)propyl)phenothiazine-2-carbonitrileChEBI
2-Cyano-10-(3-(4-hydroxy-1-piperidyl)propyl)phenothiazineChEBI
2-Cyano-10-(3-(4-hydroxypiperidino)propyl)phenothiazineChEBI
Cyano-3 ((hydroxy-4 piperidyl-1)-3 propyl)-10 phenothiazineChEBI
PericiazinaChEBI
PericiazinumChEBI
PiperocyanomazineChEBI
PericiazineKegg
NeuleptilKegg
PericyazineHMDB
AoleptHMDB
NeuleptylHMDB
PropericiazineChEBI
Chemical FormulaC21H23N3OS
Average Molecular Weight365.492
Monoisotopic Molecular Weight365.156183063
IUPAC Name10-[3-(4-hydroxypiperidin-1-yl)propyl]-10H-phenothiazine-2-carbonitrile
Traditional Namepropericiazine
CAS Registry Number2622-26-6
SMILES
OC1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C#N)CC1
InChI Identifier
InChI=1S/C21H23N3OS/c22-15-16-6-7-21-19(14-16)24(18-4-1-2-5-20(18)26-21)11-3-10-23-12-8-17(25)9-13-23/h1-2,4-7,14,17,25H,3,8-13H2
InChI KeyLUALIOATIOESLM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Piperidine
  • Benzenoid
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carbonitrile
  • Nitrile
  • Azacycle
  • Thioether
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point116 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.059 g/LNot Available
LogP3.52HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available186.622http://allccs.zhulab.cn/database/detail?ID=AllCCS00001155
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP3.78ALOGPS
logP3.11ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.18ChemAxon
pKa (Strongest Basic)8.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.4 m³·mol⁻¹ChemAxon
Polarizability40.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.71531661259
DarkChem[M-H]-181.45831661259
DeepCCS[M+H]+185.66630932474
DeepCCS[M-H]-183.27530932474
DeepCCS[M-2H]-217.30230932474
DeepCCS[M+Na]+192.72930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PropericiazineOC1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C#N)CC14251.2Standard polar33892256
PropericiazineOC1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C#N)CC13308.8Standard non polar33892256
PropericiazineOC1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C#N)CC13454.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propericiazine,1TMS,isomer #1C[Si](C)(C)OC1CCN(CCCN2C3=CC=CC=C3SC3=CC=C(C#N)C=C32)CC13307.3Semi standard non polar33892256
Propericiazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCN(CCCN2C3=CC=CC=C3SC3=CC=C(C#N)C=C32)CC13499.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Propericiazine EI-B (Non-derivatized)splash10-03xu-7932000000-163720fa7ee8e5adf3132017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propericiazine EI-B (Non-derivatized)splash10-03di-4931000000-bc6eaf361b17af48a30f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propericiazine EI-B (Non-derivatized)splash10-03xu-7932000000-163720fa7ee8e5adf3132018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propericiazine EI-B (Non-derivatized)splash10-03di-4931000000-bc6eaf361b17af48a30f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propericiazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btl-9443000000-0bf7e572c89eab0eebe02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propericiazine GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9532200000-0fac63dfe3ca1b1e5d682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propericiazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 10V, Positive-QTOFsplash10-00kb-0009000000-ea2a928d0b477b642d282016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 20V, Positive-QTOFsplash10-00kb-1319000000-d734a3c87a7e3896e9192016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 40V, Positive-QTOFsplash10-05x0-4941000000-090633fd54a2d8de3a652016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 10V, Negative-QTOFsplash10-03di-0009000000-2c21e3a159ee7e81d8922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 20V, Negative-QTOFsplash10-0nvj-0094000000-6287516a8e31f1411d1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 40V, Negative-QTOFsplash10-00di-4690000000-8c2afe6a37eb44b042352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 10V, Positive-QTOFsplash10-014i-0009000000-3bd5b70543953e9fd1fa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 20V, Positive-QTOFsplash10-00xu-0907000000-bed0c5fa41577c9ffdc32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 40V, Positive-QTOFsplash10-00di-7794000000-f64312cc0eaedb8565282021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 10V, Negative-QTOFsplash10-03di-0009000000-b9605fed856fbbd878112021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 20V, Negative-QTOFsplash10-03di-0059000000-7912c18269b0b9534e792021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propericiazine 40V, Negative-QTOFsplash10-00di-0292000000-ff380871c3b00965659f2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01608 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01608 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01608
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4585
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPericiazine
METLIN IDNot Available
PubChem Compound4747
PDB IDNot Available
ChEBI ID31981
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Tsukamoto T, Asakura M, Hirata N, Imafuku J, Matsui H, Hasegawa K: Interaction of neuroleptics and antidepressants with rat brain alpha 2-receptors: a possible relationship between alpha 2-receptor antagonism and antidepressant action. Biol Psychiatry. 1984 Sep;19(9):1283-91. [PubMed:6149771 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
References
  1. Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. [PubMed:7918347 ]