Ciclopramine

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Ciclopramine
Clinical data

ATC code	None
Legal status
Legal status	Not marketed
Identifiers
IUPAC name N-Methyl-2,3,7,8-tetrahydro-1H-quino[1,8-ab][1]benzazepin-3-amine
CAS Number	33545-56-1
PubChem CID	160410
ChemSpider	140965
UNII	BXS8X8APGS
ChEMBL	ChEMBL2105933
Chemical and physical data
Formula	C₁₈H₂₀N₂
Molar mass	264.372 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c14c2c(ccc1)C(NC)CCN2c3ccccc3CC4

Ciclopramine is a tetracyclic antidepressant (TeCA) that was never marketed.^[1]^[2]

References[]

^ Triggle DJ (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
^ Saletu B (1982). "Pharmaco-EEG profiles of typical and atypical antidepressants". Advances in Biochemical Psychopharmacology. 32: 257–68. PMID 7090895.

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIs	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIs	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIs	Atomoxetine Reboxetine Viloxazine
NDRIs	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAs	Mianserin Mirtazapine Setiptiline
SARIs	Etoperidone Nefazodone Trazodone
SMS	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Esketamine Etryptamine^‡ Indeloxazine flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAs	Amineptine^‡ Amitriptyline^# Amitriptylinoxide 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	Amoxapine 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-selective	Reversible: Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_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) 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 Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (TCAs and TeCAs)	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Esmirtazapine Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Naranol Nitroxazepine Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline (teciptiline) Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Clocapramine Clorotepine Clotiapine Clozapine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Levomepromazine/Methotrimeprazine Loxapine Lurasidone Mesoridazine Metiapine Metitepine Mosapramine Naranol Olanzapine Oxyprothepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Trifluoperazine Triflupromazine Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline
Others	Adosopine Atiprosin Benzoctamine Carvedilol Cidoxepin Cyclobenzaprine Methylene blue Monatepil Oxetorone Perlapine Pipazethate P7C3 Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Telenzepine Tropatepine

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