Promazine (CHEM002091)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (16)XML
Record Information
Version1.0
Creation Date2009-07-05 03:15:17 UTC
Update Date2026-03-31 19:07:43 UTC
Accession NumberCHEM002091
Identification
Common NamePromazine
ClassSmall Molecule
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. 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antiemetic
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Phenothiazine
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass284.419 g/mol
Monoisotopic Mass284.135 g/mol
CAS Registry Number58-40-2
IUPAC Namedimethyl[3-(10H-phenothiazin-10-yl)propyl]amine
Traditional Namepromazine
SMILESCN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceOily liquid (7).
Experimental Properties
PropertyValue
Melting Point< 25°C
Boiling Point203-210°C at 3.00E-01 mm Hg
Solubility14.2 mg/L (at 24°C)
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4r-9230000000-62cbfd979fa705bc6b5eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053i-9470000000-c8ea76fcc1b124b82db0Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-2090000000-c38077fbc5880feb7eabSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4r-9230000000-62cbfd979fa705bc6b5eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053i-9470000000-c8ea76fcc1b124b82db0Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-2090000000-c38077fbc5880feb7eabSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bt9-9380000000-4268602a9238fb15661cSpectrum
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, Positivesplash10-000i-1090000000-ae84d127d484047e5016Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-5090000000-5d46ceef0ced8c3b4fd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9220000000-fb2bc50e3fc843771469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-149bf8914d943f700602Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00aj-0940000000-c0e629447aac15d08168Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2900000000-5d376e3b361f6d4469ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1090000000-eb710b269048129dc354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9020000000-e2fb252f33540e1240dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-7887c8f93cf8f9148ae9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-34b5b095a83ae223858eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0490000000-8b3f6932ff0b667dd708Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0910000000-8b82ae7472d26c1d3bdbSpectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9430000000-708a7cbef8d61ce76846Spectrum
Toxicity Profile
Route of ExposureInhalation; dermal or skin contact; ingestion (MSDS, A308). Absorption may be erratic and peak plasma concentrations show large interindividual differences.
Mechanism of ToxicityPromazine 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.
MetabolismHepatic, primarily to N-desmethylpromazine and promazine sulfoxide. Absorption may be erratic and peak plasma concentrations show large interindividual differences. The metabolism occurs through oxidative processes mediated largely by hepatic microsomal and other drug metabolizing enzymes. Antoher step is the conjugaion with glucuronic acid. Other reactions include hydroxylation, demetylation, and sulfoxide formation. Moreover, metabolic alterations in side chain may also occur (1, 2).
Toxicity ValuesLD50: 140 mg/kg (Intraperitoneal, Mouse)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as an adjunct for short term treatment of moderate and severe psychomotor agitation. Also used to treat agitation or restlessness in the elderly.
Minimum Risk LevelNot Available
Health EffectsIt has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon either. Other effects include endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia (1, 5).
SymptomsSide effects include: extrapyramidal symptoms, drowsiness, weight gain, dry mouth, constipation, endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia.
TreatmentIn severe cases, consider supportive therapy. Maintain clear airway and adequate hydration. Anti-Parkinson drugs, as well as benztropine mesylate, and barbiturates can be use to relieve extrapyramidal symptoms (3).
Concentrations
Not Available
DrugBank IDDB00420
HMDB IDHMDB0014564
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPromazine
Chemspider ID4757
ChEBI ID8459
PubChem Compound ID4926
Kegg Compound IDC07379
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18423639
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19306624
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390