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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:40:28 UTC
Update Date2019-07-23 14:38:54 UTC
HMDB IDHMDB0240235
Secondary Accession NumbersNone
Metabolite Identification
Common NameThiazinamium
DescriptionThiazinamium 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. Since many of the uses of antihistamines involve conditions such as rashes, which should be treatable by local application, there is some rationale for developing drugs for topical use. Thiazinamium is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, thiazinamium is involved in the metabolic disorder called the thiazinamium h1-antihistamine action pathway. Thiazinamium metilsulfate (INN) or thiazinam is an antihistamine. The USAN is thiazinamium chloride (with a different counterion). The known poor absorption of quat salts make such derivatives attractive for nonabsorbable antihistamines for topical use. Thus, reaction of the well-known antihistaminic drug promethazine with methylchloride leads to thiazinamium chloride. The known side effects of antihistamines could in principle be avoided if the drug were functionalized to avoid systemic absorption.
Structure
Data?1563892734
Synonyms
ValueSource
ThiazinamonHMDB
ThiazinamHMDB
Thiazinamium metilsulfateHMDB
ThiazinamiumHMDB
MulterganMeSH, HMDB
MethylpromethazineMeSH, HMDB
Chemical FormulaC18H23N2S
Average Molecular Weight299.46
Monoisotopic Molecular Weight299.157646343
IUPAC Nametrimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]azanium
Traditional Namethiazinamium metilsulfate
CAS Registry Number2338-21-8
SMILES
CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)[N+](C)(C)C
InChI Identifier
InChI=1S/C18H23N2S/c1-14(20(2,3)4)13-19-15-9-5-7-11-17(15)21-18-12-8-6-10-16(18)19/h5-12,14H,13H2,1-4H3/q+1
InChI KeyCDXCCYNINPIWGE-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
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Tertiary amine
  • Thioether
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic salt
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.26ALOGPS
logP0.13ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity104.42 m³·mol⁻¹ChemAxon
Polarizability34.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-9040000000-32726e2129d72228ab00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-bf4111375aca3b2c6c20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gvo-2290000000-61983106de91af130780Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ik9-1390000000-1b46cfd2cc41657e7ef4Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13420
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiazinamium metilsulfate
METLIN IDNot Available
PubChem Compound6016
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gilfillan AM, Lewis AJ, Rooney SA: Effects of thiazinamium chloride and other antihistamines on phosphatidylcholine secretion in rat type II pneumocyte cultures. Biochem Pharmacol. 1987 Jan 15;36(2):277-81. [PubMed:2880592 ]