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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014564
Secondary Accession Numbers
  • HMDB14564
Metabolite Identification
Common NamePromazine
DescriptionPromazine is only found in individuals that have used or taken this drug. It is a phenothiazine with actions similar to chlorpromazine but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic. [PubChem]Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine.
Structure
Data?1582753193
Synonyms
ValueSource
10-(3-(Dimethylamino)propyl)phenothiazineChEBI
N-(3-Dimethylaminopropyl)phenothiazineChEBI
N-Dimethylamino-1-methylethyl thiodiphenylamineChEBI
PromazinaChEBI
PromazinumChEBI
CombelenKegg
PromazinHMDB
ProtactylHMDB
Promazine hydrochlorideHMDB
Hydrochloride, promazineHMDB
SinopheninHMDB
SparineHMDB
Chemical FormulaC17H20N2S
Average Molecular Weight284.419
Monoisotopic Molecular Weight284.13471934
IUPAC Namedimethyl[3-(10H-phenothiazin-10-yl)propyl]amine
Traditional Namepromazine
CAS Registry Number58-40-2
SMILES
CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12
InChI Identifier
InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3
InChI KeyZGUGWUXLJSTTMA-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
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.021 g/LNot Available
LogP4.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM161.530932474
[M+H]+Not Available161.363http://allccs.zhulab.cn/database/detail?ID=AllCCS00000985
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP4.63ALOGPS
logP3.93ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.95 m³·mol⁻¹ChemAxon
Polarizability32.74 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.90931661259
DarkChem[M-H]-163.44131661259
DeepCCS[M-2H]-189.01330932474
DeepCCS[M+Na]+164.57830932474
AllCCS[M+H]+165.832859911
AllCCS[M+H-H2O]+162.532859911
AllCCS[M+NH4]+168.932859911
AllCCS[M+Na]+169.732859911
AllCCS[M-H]-169.732859911
AllCCS[M+Na-2H]-169.232859911
AllCCS[M+HCOO]-168.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PromazineCN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C123325.5Standard polar33892256
PromazineCN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C122314.2Standard non polar33892256
PromazineCN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C122308.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Promazine EI-B (Non-derivatized)splash10-0a4r-9230000000-62cbfd979fa705bc6b5e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Promazine EI-B (Non-derivatized)splash10-053i-9470000000-c8ea76fcc1b124b82db02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Promazine CI-B (Non-derivatized)splash10-000i-2090000000-c38077fbc5880feb7eab2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Promazine EI-B (Non-derivatized)splash10-0a4r-9230000000-62cbfd979fa705bc6b5e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Promazine EI-B (Non-derivatized)splash10-053i-9470000000-c8ea76fcc1b124b82db02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Promazine CI-B (Non-derivatized)splash10-000i-2090000000-c38077fbc5880feb7eab2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Promazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bt9-9380000000-4268602a9238fb15661c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Promazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Promazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9430000000-708a7cbef8d61ce768462014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 10V, Positive-QTOFsplash10-000i-1090000000-ae84d127d484047e50162016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 20V, Positive-QTOFsplash10-000l-5090000000-5d46ceef0ced8c3b4fd32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 40V, Positive-QTOFsplash10-0006-9220000000-fb2bc50e3fc8437714692016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 10V, Negative-QTOFsplash10-001i-0090000000-149bf8914d943f7006022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 20V, Negative-QTOFsplash10-00aj-0940000000-c0e629447aac15d081682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 40V, Negative-QTOFsplash10-0002-2900000000-5d376e3b361f6d4469ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 10V, Positive-QTOFsplash10-000i-1090000000-eb710b269048129dc3542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 20V, Positive-QTOFsplash10-000i-9020000000-e2fb252f33540e1240df2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 40V, Positive-QTOFsplash10-0a4i-9100000000-7887c8f93cf8f9148ae92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 10V, Negative-QTOFsplash10-001i-0090000000-34b5b095a83ae223858e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 20V, Negative-QTOFsplash10-001i-0490000000-8b3f6932ff0b667dd7082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promazine 40V, Negative-QTOFsplash10-0002-0910000000-8b82ae7472d26c1d3bdb2021-09-24Wishart 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 DB00420 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00420 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00420
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4757
KEGG Compound IDC07379
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPromazine
METLIN IDNot Available
PubChem Compound4926
PDB IDNot Available
ChEBI ID8459
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