Dimetacrine

Dimetacrine
Clinical data
Trade names	Istonil, Istonyl, Linostil, Miroistonil
Other names	Dimethacrine, acripramine
Routes of; administration	Oral
ATC code	N06AA18 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Identifiers
	IUPAC name 3-(9,9-Dimethylacridin-10-yl)-N,N-dimethyl-propan-1-amine;
CAS Number	4757-55-5;
PubChem CID	94280;
DrugBank	DB08996 ;
ChemSpider	85085;
UNII	O341NY501N;
KEGG	D02565;
CompTox Dashboard (EPA)	DTXSID4022941 ;
Chemical and physical data
Formula	C20H26N2
Molar mass	294.442 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(C2=CC=CC=C2N(C3=CC=CC=C31)CCCN(C)C)C;

Dimetacrine (also known as dimethacrine and acripramine; brand names Istonil, Istonyl, Linostil, and Miroistonil) is a tricyclic antidepressant (TCA) used in Europe and formerly in Japan for the treatment of depression.^[2]^[3]^[4]^[5]^[6] It has imipramine-like effects; though, in a double-blind clinical trial against imipramine, dimetacrine was found to have lower efficacy in comparison and produced more weight loss and abnormal liver tests.^[7]^[8]

Little is known about the pharmacology of dimetacrine,^[9] but it can be inferred that it acts in a similar manner to other TCAs. If this is indeed the case, dimetacrine may induce severe cardiac toxicity in overdose (a side effect unique to the tricyclic class of antidepressants).

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
^ Kato S (1993). "A Review of the Pharmacotherapy of Depression in Japan". In Kariya T, Nakagawara M (eds.). Affective Disorders: Perspective on Basic Research and Clinical Practice. Tokyo: Seiwa Shoten. ISBN 978-0-87630-674-1.
^ Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. ISBN 978-3-527-31058-6.
^ Taen S, Pöldinger W (December 1966). "[Dimethacrine (istonil), an acridane derivative with the antidepressive action]". Schweizerische Medizinische Wochenschrift (in German). 96 (48): 1616–1620. PMID 6008540.
^ Meyer R (May 1968). "[Contribution to the clinical evaluation of the antidepressive effect of dimethacrine (Istonil)]". Praxis (in German). 57 (20): 721–723. PMID 5756370.
^ Abuzzahab FS (November 1973). "A double-blind investigation of dimethacrine versus imipramine in hospitalized depressive states". International Journal of Clinical Pharmacology, Therapy and Toxicology. 8 (3): 244–253. PMID 4149236.
^ Mutschler E, Derendorf H (1995). "Psychoactive Drugs: Antidepresants". Drug actions: basic principles and therapeutic aspects. Stuttgart, Germany: Medpharm Scientific Pub. ISBN 0-8493-7774-9. Retrieved January 30, 2013.
^ "Dimetacrine". PubChem. U.S. National Library of Medicine. Retrieved 2023-11-03.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[isbn0-412-54090-8-2] Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.

[3] Kato S (1993). "A Review of the Pharmacotherapy of Depression in Japan". In Kariya T, Nakagawara M (eds.). Affective Disorders: Perspective on Basic Research and Clinical Practice. Tokyo: Seiwa Shoten. ISBN 978-0-87630-674-1.

[Vela_2007-4] Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. ISBN 978-3-527-31058-6.

[pmid6008540-5] Taen S, Pöldinger W (December 1966). "[Dimethacrine (istonil), an acridane derivative with the antidepressive action]". Schweizerische Medizinische Wochenschrift (in German). 96 (48): 1616–1620. PMID 6008540.

[pmid5756370-6] Meyer R (May 1968). "[Contribution to the clinical evaluation of the antidepressive effect of dimethacrine (Istonil)]". Praxis (in German). 57 (20): 721–723. PMID 5756370.

[pmid4149236-7] Abuzzahab FS (November 1973). "A double-blind investigation of dimethacrine versus imipramine in hospitalized depressive states". International Journal of Clinical Pharmacology, Therapy and Toxicology. 8 (3): 244–253. PMID 4149236.

[isbn0-8493-7774-9-8] Mutschler E, Derendorf H (1995). "Psychoactive Drugs: Antidepresants". Drug actions: basic principles and therapeutic aspects. Stuttgart, Germany: Medpharm Scientific Pub. ISBN 0-8493-7774-9. Retrieved January 30, 2013.

[9] "Dimetacrine". PubChem. U.S. National Library of Medicine. Retrieved 2023-11-03.

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v t e Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (Tricyclic antidepressants (TCAs))	Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Batelapine Beloxepin Butriptyline Cianopramine Ciclazindol Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mirtazapine Monometacrine Nitroxazepine Norbutriptyline Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Cidoxepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Dioxopromethazine Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Perlapine Phenindamine Pimethixene Pirolate Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline
Anticholinergics	Darenzepine Dipitramine Nuvenzepine Pirenzepine Profenamine Rispenzepine Siltenzepine Telenzepine Tripitramine Tropatepine Zolenzepine
Others	Adosopine Aminopromazine Atiprosin Benzoctamine Botiacrine Carvedilol Cyclobenzaprine Damotepine Elanzepine Fluradoline Methylene blue Monatepil Oxetorone Pipazethate P7C3 P7C3-A20 Pinadoline Pitrazepin Pizotifen Serazapine Tipindole

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See also

References