Sertraline hydrochloride (CHEM017533)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:26:27 UTC
Update Date2016-11-09 01:15:36 UTC
Accession NumberCHEM017533
Identification
Common NameSertraline hydrochloride
ClassSmall Molecule
DescriptionA hydrochloride resulting from the reaction of equimolar amounts of sertraline and hydrogen chloride. A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as an antidepressant for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic stress disorder.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-cis-(1S,4S)-1-Methylamino-4-(3,4-dichlorophenyl)tetralin hydrochlorideChEBI
(+)-Sertraline hydrochlorideChEBI
(1S,4S)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-aminium chlorideChEBI
(1S-cis)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochlorideChEBI
LustralChEBI
Sertraline HCLChEBI
ZoloftChEBI
apo SertralineMeSH
apo-SertralineMeSH
AremisMeSH
Boehringer ingelheim brand OF sertraline hydrochlorideMeSH
Esteve brand OF sertraline hydrochlorideMeSH
Pfizer brand OF sertraline hydrochlorideMeSH
BesitranMeSH
Gen sertralineMeSH
GlademMeSH
novo SertralineMeSH
Parke davis brand OF sertraline hydrochlorideMeSH
Ratiopharm brand OF sertraline hydrochlorideMeSH
Rhoxal sertralineMeSH
Sertraline hydrochloride (1S-cis)-isomerMeSH
Apotex brand OF sertraline hydrochlorideMeSH
Gen-sertralineMeSH
Genpharm brand OF sertraline hydrochlorideMeSH
Hydrochloride, sertralineMeSH
Lacer brand OF sertraline hydrochlorideMeSH
Rhoxal-sertralineMeSH
SertralineMeSH
AltrulineMeSH
novo-SertralineMeSH
Novopharm brand OF sertraline hydrochlorideMeSH
Rhoxalpharma brand OF sertraline hydrochlorideMeSH
Roerig brand OF sertraline hydrochlorideMeSH
SealdinMeSH
ratio SertralineMeSH
ratio-SertralineMeSH
Chemical FormulaC17H18Cl3N
Average Molecular Mass342.691 g/mol
Monoisotopic Mass341.050 g/mol
CAS Registry Number79559-97-0
IUPAC Name(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride
Traditional Namesertraline hydrochloride
SMILESCl.[H][C@@]1(CC[C@@]([H])(C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12)NC
InChI IdentifierInChI=1S/C17H17Cl2N.ClH/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11;/h2-6,8,10,12,17,20H,7,9H2,1H3;1H/t12-,17-;/m0./s1
InChI KeyBLFQGGGGFNSJKA-XHXSRVRCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tametralines. Tametralines are compounds containing a tametraline moiety, which consists of a tetrahydronaphthalene linked to a phenyl group to form N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine skeleton.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassTametralines
Direct ParentTametralines
Alternative Parents
Substituents
  • Tametraline
  • 1,2-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Secondary aliphatic amine
  • Secondary amine
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Hydrochloride
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00014 g/LALOGPS
logP5.06ALOGPS
logP5.15ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.74 m³·mol⁻¹ChemAxon
Polarizability32.33 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bt9-2910000000-0b06eaf7c5740b79e7f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-967bc9f43fb09efdda1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-967bc9f43fb09efdda1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0009000000-967bc9f43fb09efdda1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-0f7128920097fcaedee1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-0f7128920097fcaedee1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-0f7128920097fcaedee1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000808
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSertraline
Chemspider IDNot Available
ChEBI ID9124
PubChem Compound ID63009
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10184609
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12093324
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12387695
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12452737
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12701343
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12772794
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=14596660
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17661734
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18980823
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19026250
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19370626
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=19502000
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19584964
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=20383937
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=20393946
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=20457874
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=20953053
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21070110
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21456103
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=21823671
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=8342482
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=8675965