Desmethylcitalopram

Chemical compound

Pharmaceutical compound

Desmethylcitalopram
Clinical data
Skeletal formula of desmethylcitalopram /
Space-filling model of the desmethylcitalopram molecule
ATC code	none
Legal status
Legal status	In general: uncontrolled
Pharmacokinetic data
Elimination half-life	50 h
Identifiers
IUPAC name (RS/S)-1-[3-(Methylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number	62498-67-3 ^☒N
PubChem CID	162180
ChemSpider	142424 ^☒N
UNII	3KBX9104IR
CompTox Dashboard (EPA)	DTXSID90881082 Edit this at Wikidata
ECHA InfoCard	100.057.776 Edit this at Wikidata
Chemical and physical data
Formula	C₁₉H₁₉FN₂O
Molar mass	310.372 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CNCCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
InChI 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^☒N Key:PTJADDMMFYXMMG-UHFFFAOYSA-N^☒N
^☒NcheckY (what is this?) (verify)

Desmethylcitalopram is an active metabolite of the antidepressant drugs citalopram (racemic) and escitalopram (the S-enantiomer, which would be called desmethylescitalopram).^[1]^[2] Like citalopram and escitalopram, desmethylcitalopram functions as a selective serotonin reuptake inhibitor (SSRI), and is responsible for some of its patient's therapeutic benefits.

References

[edit ]

^ "Desmethylcitalopram". Human Metabolome Database.
^ Brøsen K, Naranjo CA (August 2001). "Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram". European Neuropsychopharmacology. 11 (4): 275–83. doi:10.1016/s0924-977x(01)00101-8. PMID 11532381. S2CID 11837037.

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Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIs Tooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine ^# Fluvoxamine Indalpine ^‡ Paroxetine Sertraline Zimelidine ^‡
SNRIs Tooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIs Tooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIs Tooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine ^‡ Bupropion Nomifensine ^‡
NaSSAs Tooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIs Tooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMS Tooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine ^‡ Gepirone Indeloxazine Flupentixol Ketamine ^§ Medifoxamine ^‡ Metryptamine ^‡ Oxaflozane ^‡ Pivagabine ^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAs Tooltip Tricyclic antidepressants	Amineptine ^‡ Amitriptyline ^# Amitriptylinoxide Amoxapine Butriptyline ^‡ Clomipramine ^# Demexiptiline ^‡ Desipramine Dibenzepin Dimetacrine ^‡ Dosulepin Doxepin Imipramine Imipraminoxide ^‡ Iprindole ^‡ Lofepramine Melitracen Metapramine ^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine ^‡ Protriptyline Quinupramine ^‡ Tianeptine Trimipramine
TeCAs Tooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin ^‡ Iproclozide ^‡ Iproniazid ^‡ Isocarboxazid Isoniazid ^# Linezolid ^# Mebanazine ^‡ Nialamide ^‡ Octamoxin ^‡ Phenelzine Pheniprazine ^‡ Phenoxypropazine ^‡ Pivhydrazine ^‡ Safrazine ^‡ Tedizolid Tranylcypromine Reversible: Caroxazone ^‡ Mixed: Bifemelane
MAO_A Tooltip Monoamine oxidase A-selective	Reversible: Eprobemide Metralindole Minaprine ^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_B Tooltip Monoamine oxidase B-selective	Irreversible: Selegiline

Adjunctive therapies
Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous
Ademetionine (SAMe) GABAkine neurosteroids (brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Monoamine reuptake inhibitors
DAT Tooltip Dopamine transporter (DRIs Tooltip Dopamine reuptake inhibitors)	Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 JJC8-088 Nefazodone Vanoxerine Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol Dexmethylphenidate Difemetorex Ethylphenidate HDMP-28 Methylphenidate Pethidine (meperidine) Phencyclidine Pipradrol Serdexmethylphenidate Tenocyclidine Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone Tropanes: Altropane Benzatropine (benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine (ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) RTI-55 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33 Others: Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102,677 DOV-216,303 Efavirenz Ephenidine Esketamine EXP-561 Fencamfamin Fezolamine Fluorenol GYKI-52895 Hydroxybupropion Indatraline Ketamine Lafadofensine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117 (WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Threohydrobupropion Tripelennamine Venlafaxine
NET Tooltip Norepinephrine transporter (NRIs Tooltip Norepinephrine reuptake inhibitors)	Selective norepinephrine reuptake inhibitors: Amedalin Alseroxylon Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Teniloxazine Viloxazine Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) CP-39,332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA Nafenodone PPPA Tofenacin Venlafaxine Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine) Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., ketamine, phencyclidine) Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol)
SERT Tooltip Serotonin transporter (SRIs Tooltip Serotonin reuptake inhibitors)	Selective serotonin reuptake inhibitors: 6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Norfluoxetine Omiloxetine Panuramine Paroxetine PIM-35 Pirandamine RTI-353 Seproxetine Sertraline Zimelidine Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) Bicifadine CP-39332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA PPPA Tofenacin Venlafaxine Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine) Tricyclic antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine) Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol) Roxindole
VMATs Tooltip Vesicular monoamine transporters	Amiodarone Amphetamines (e.g., amphetamine, methamphetamine, MDMA) APP AZIK Bietaserpine Deserpidine Deutetrabenazine Dihydrotetrabenazine Efavirenz GBR-12935 GZ-793A Ibogaine Ketanserin Lobeline Methoxytetrabenazine Reserpine Rose bengal Tetrabenazine Valbenazine Vanoxerine (GBR-12909)
Others	Unsorted: Cendifensine DAT enhancers: Luteolin DAT modulators: Agonist-like: SoRI-9804 SoRI-20040; Antagonist-like: SoRI-20041
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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References