Dimetacrine

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 3-(9,9-Dimethylacridin-10-yl)-N,N-dimethyl-propan-1-amine

| image = Dimetacrine v2.svg

| width = 150

| image_class = skin-invert-image

| alt = Skeletal formula of dimetacrine

| image2 = Dimetacrine-3D-balls.png

| alt2 = Ball-and-stick model of the dimetacrine molecule

| width2 = 175

| tradename = Istonil, Istonyl, Linostil, Miroistonil

| pregnancy_category =

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA =

| legal_DE =

| legal_NZ =

| legal_UK =

| legal_US =

| legal_EU =

| legal_UN =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

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| synonyms = Dimethacrine, acripramine

| CAS_number = 4757-55-5

| ATC_prefix = N06

| ATC_suffix = AA18

| PubChem = 94280

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB08996

| ChemSpiderID = 85085

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = O341NY501N

| KEGG = D02565

| C=20 | H=26 | N=2

| 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.{{cite book | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | isbn = 0-412-54090-8 | url = https://books.google.com/books?id=_8TyJT0RfN0C&pg=PA2519}}{{cite book | vauthors = Kato S | chapter = A Review of the Pharmacotherapy of Depression in Japan | veditors = Kariya T, Nakagawara M |title=Affective Disorders: Perspective on Basic Research and Clinical Practice |date=1993 |publisher=Seiwa Shoten |location=Tokyo |isbn=978-0-87630-674-1 | chapter-url = https://books.google.com/books?id=XLItppcgYugC&pg=PA117 }}{{cite book | vauthors = Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A | title = Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application | publisher = Wiley-VCH | location = Weinheim | year = 2007 | isbn = 978-3-527-31058-6 }}{{cite journal | vauthors = Taen S, Pöldinger W | title = [Dimethacrine (istonil), an acridane derivative with the antidepressive action] | language = de | journal = Schweizerische Medizinische Wochenschrift | volume = 96 | issue = 48 | pages = 1616–1620 | date = December 1966 | pmid = 6008540 }}{{cite journal | vauthors = Meyer R | title = [Contribution to the clinical evaluation of the antidepressive effect of dimethacrine (Istonil)] | language = de | journal = Praxis | volume = 57 | issue = 20 | pages = 721–723 | date = May 1968 | pmid = 5756370 }} 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.{{cite journal | vauthors = Abuzzahab FS | title = A double-blind investigation of dimethacrine versus imipramine in hospitalized depressive states | journal = International Journal of Clinical Pharmacology, Therapy and Toxicology | volume = 8 | issue = 3 | pages = 244–253 | date = November 1973 | pmid = 4149236 }}{{cite book | vauthors = Mutschler E, Derendorf H | chapter = Psychoactive Drugs: Antidepresants | title = Drug actions: basic principles and therapeutic aspects | publisher = Medpharm Scientific Pub | location = Stuttgart, Germany | year = 1995 | isbn = 0-8493-7774-9 | chapter-url = https://books.google.com/books?id=IvN4mZxraMkC&q=dimetacrine&pg=PA127 | access-date = January 30, 2013}}

Little is known about the pharmacology of dimetacrine,{{Cite web | work = PubChem | publisher = U.S. National Library of Medicine |title=Dimetacrine |url=https://pubchem.ncbi.nlm.nih.gov/compound/94280 |access-date=2023-11-03 |language=en}} 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).