ContaminantDB: N-desmethylcitalopram

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 10:51:33 UTC

Update Date

2016-11-09 01:22:54 UTC

Accession Number

CHEM043373

Identification

Common Name

N-desmethylcitalopram

Class

Small Molecule

Description

Desmethylcitalopram is an active metabolite of the antidepressant drugs citalopram (racemic) and escitalopram (the S-enantiomer, which would be called desmethylescitalopram). Like citalopram and escitalopram, desmethylcitalopram functions as a selective serotonin reuptake inhibitor (SSRI), and is responsible for some of its parents' therapeutic benefits.

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Desmethyl-escitalopram	MeSH
Desmethylcitalopram	MeSH

Chemical Formula

C₁₉H₁₉FN₂O

Average Molecular Mass

310.372 g/mol

Monoisotopic Mass

310.148 g/mol

CAS Registry Number

144025-14-9

IUPAC Name

(1S)-1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-1,3-dihydro-2-benzofuran-5-carbonitrile

Traditional Name

(1S)-1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-3H-2-benzofuran-5-carbonitrile

SMILES

CNCCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C19H19FN2O/c1-22-10-2-9-19(16-4-6-17(20)7-5-16)18-8-3-14(12-21)11-15(18)13-23-19/h3-8,11,22H,2,9-10,13H2,1H3/t19-/m0/s1

InChI Key

PTJADDMMFYXMMG-IBGZPJMESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Isocoumaran
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Dialkyl ether
Secondary aliphatic amine
Ether
Carbonitrile
Nitrile
Oxacycle
Secondary amine
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0052 g/L	ALOGPS
logP	3.24	ALOGPS
logP	3.38	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	10.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.73 m³·mol⁻¹	ChemAxon
Polarizability	33.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-1098000000-21dde1b3364c57dbdd76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-1191000000-d1e1b3147cb08a67eaf5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06dl-9540000000-33ba0b6b7cabe983d4fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1009000000-11570b53909e284c90a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1049000000-5002b93fb410b5342dcb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6t-4290000000-981b4ff89efe87c1d73e	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Desmethylcitalopram

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

11255350

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

N-desmethylcitalopram (CHEM043373)

Structure for CHEM043373: N-desmethylcitalopram