ciclindole

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

| image = Ciclindole.png

| width =

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| CAS_number = 32211-97-5

| ATC_prefix = None

| ATC_suffix =

| PubChem = 36082

| ChEMBL = 2104160

| ChemSpiderID = 33189

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

| UNII = CXJ7G6BYD7

| KEGG = D03619

| synonyms = WIN-27,147-2; WIN-27147-2; WIN27147-2

| C=14 | H=18 | N=2

| SMILES = c21c(cccc1)[nH]c3c2CC(N(C)C)CC3

}}

Ciclindole ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code name WIN-27,147-2), also known as cyclindole ({{Abbrlink|USAN|United States Adopted Name}}), is an antipsychotic with a tricyclic and tryptamine-like structure that was never marketed.{{cite book | first = David J. | last = Triggle | name-list-style = vanc | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&q=cyclindole&pg=PA540}}{{cite journal | vauthors = Wood PL, McQuade PS | title = Ciclindole and flucindole: novel tetrahydrocarbazolamine neuroleptics | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 8 | issue = 4–6 | pages = 773–7 | year = 1984 | pmid = 6152347 | doi = 10.1016/0278-5846(84)90057-5 | s2cid = 39252411 }}

It displaces spiperone binding in vitro and elevates dopamine levels in the striatum, indicating that it acts as a dopamine D₂ receptor antagonist. It also shows apparent affinity for the α₁-adrenergic receptor, the serotonin S₁ receptor, and the serotonin S₂ receptor. However, its affinities for all of the preceding targets are weak, in the low micromolar range.

The related drug flucindole is about 5 to 10{{nbsp}}times more potent than ciclindole both in vitro and in vivo.