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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:38:20 UTC
Update Date2019-07-23 14:38:52 UTC
HMDB IDHMDB0240228
Secondary Accession NumbersNone
Metabolite Identification
Common NameFenethazine
DescriptionFenethazine, also known as etisin or ethysine, 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. Fenethazine (INN) (brand names Anergen, Contralergial, Ethysine, Etisine, Lisergan, Lysergan; former developmental code names RP-3015, SC-1627, WY-1143), or phenethazine, is a first-generation antihistamine of the phenothiazine group. Fenethazine is a very strong basic compound (based on its pKa). In humans, fenethazine is involved in fenethazine h1-antihistamine action. Fenethazine, in turn, was derived from phenbenzamine. Promethazine, and subsequently chlorpromazine, were derived from fenethazine.
Structure
Data?1563892732
Synonyms
ValueSource
PHENETHAZINEHMDB
EthysineHMDB
Abbott 2780HMDB
AnerganHMDB
AnergellHMDB
AnergenHMDB
EthizineHMDB
EthyseneHMDB
EthyzineHMDB
EtisinHMDB
EtisineHMDB
LiserganHMDB
LiserginHMDB
LyserganHMDB
PhenetazineHMDB
PhenethazinumHMDB
RuterganHMDB
SC 1627HMDB
FenethazineHMDB
Chemical FormulaC16H18N2S
Average Molecular Weight270.39
Monoisotopic Molecular Weight270.119069762
IUPAC Namedimethyl[2-(10H-phenothiazin-10-yl)ethyl]amine
Traditional Nameanergen
CAS Registry Number522-24-7
SMILES
CN(C)CCN1C2=CC=CC=C2SC2=CC=CC=C12
InChI Identifier
InChI=1S/C16H18N2S/c1-17(2)11-12-18-13-7-3-5-9-15(13)19-16-10-6-4-8-14(16)18/h3-10H,11-12H2,1-2H3
InChI KeyPFAXACNYGZVKMX-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 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
logP4.14ALOGPS
logP3.87ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.09 m³·mol⁻¹ChemAxon
Polarizability30.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1090000000-b53561f4c91ac29fa58cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-7090000000-b2adc754f848070f286dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zor-9140000000-2889229c3317e017eb15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-e9dd00b57b1f6729483bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0590000000-e857522212321e50a7a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3920000000-83054be340633ebfac68Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID61526
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenethazine
METLIN IDNot Available
PubChem Compound68223
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. Sneader W: The 50th Anniversary of Chlorpromazine. Drug News Perspect. 2002 Sep;15(7):466-471. [PubMed:12677184 ]