ContaminantDB: Didemethylcitalopram

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

Record Information

Version

1.0

Creation Date

2016-05-25 18:40:05 UTC

Update Date

2016-11-09 01:17:32 UTC

Accession Number

CHEM022577

Identification

Common Name

Didemethylcitalopram

Class

Small Molecule

Description

In humans, CITA is metabolized to demethylcitalopram (DCITA) by CYP2C19, CYP2D6, and CYP3A and to didemethylcitalopram by CYP2D6. (PMID: 19011672) The major metabolite of citalopram is demethylcitalopram, which is subsequently metabolized to the minor metabolite didemethylcitalopram (DDCT). (PMID: 22085614)

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Didesmethylcitalopram oxalate	HMDB
Didesmethylcitalopram	MeSH

Chemical Formula

C₁₈H₁₇FN₂O

Average Molecular Mass

296.339 g/mol

Monoisotopic Mass

296.132 g/mol

CAS Registry Number

Not Available

IUPAC Name

1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

Traditional Name

didemethylcitalopram

SMILES

NCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C18H17FN2O/c19-16-5-3-15(4-6-16)18(8-1-9-20)17-7-2-13(11-21)10-14(17)12-22-18/h2-7,10H,1,8-9,12,20H2

InChI Key

RKUKMUWCRLRPEJ-UHFFFAOYSA-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 halide
Aryl fluoride
Oxacycle
Dialkyl ether
Ether
Carbonitrile
Nitrile
Organoheterocyclic compound
Organohalogen compound
Organic oxygen compound
Organopnictogen compound
Primary aliphatic amine
Amine
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Primary amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic amino compound (CHEBI:80604 )
benzenes (CHEBI:80604 )

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	2.69	ALOGPS
logP	2.95	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.95 m³·mol⁻¹	ChemAxon
Polarizability	31.16 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-5190000000-27267b21fbfd2667ad0a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-0090000000-6d8ae8086154e9386c59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1190000000-a3bd6197e10242280d3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9850000000-29310282b6b9fbd8e49f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-b966c93238a3cd3d8dbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1090000000-6f09b8194f9dc7f22ae0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-5290000000-4ebf655263c971b6b6fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-1839b3c3aa4333bd08f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-0290000000-ee8bb8dcc6c4bee4016a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0930000000-59d6738739988f333915	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-009c4b2c3fd1dd912a1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-e2f03fdefbdbf6669449	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1590000000-373645739048c7d4b1c2	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

HMDB0060472

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

Not Available

Chemspider ID

Not Available

ChEBI ID

80604

PubChem Compound ID

162976

Kegg Compound ID

C16609

YMDB ID

Not Available

ECMDB ID

M2MDB005094

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011.

2. Howland RH: A critical evaluation of the cardiac toxicity of citalopram: part 2. J Psychosoc Nurs Ment Health Serv. 2011 Dec;49(12):13-6. doi: 10.3928/02793695-20111102-04. Epub 2011 Nov 16.

3. Rocha A, Coelho EB, Lanchote VL: Influence of quinidine, fluvoxamine, and ketoconazole on the enantioselective pharmacokinetics of citalopram in rats. Can J Physiol Pharmacol. 2008 Nov;86(11):770-6. doi: 10.1139/Y08-088.

Didemethylcitalopram (CHEM022577)

Structure for CHEM022577: Didemethylcitalopram