Flucindole

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Flucindole

Systematic (IUPAC) name
6,8-difluoro-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine
Clinical data
Legal status	Uncontrolled
Routes	Oral
Identifiers
CAS number	40594-09-0
ATC code	None
PubChem	CID 38531
UNII	5CYU0D0S8M^Y
KEGG	D02658^Y
Chemical data
Formula	C₁₄H₁₈N₂
Mol. mass	250.287 g/mol
SMILES CN(C)C1CCC2=C(C1)C3=CC(=CC(=C3N2)F)F
Y (what is this?) (verify)

Flucindole is an antipsychotic with a tricyclic structure, that was never marketed.^[1] It is the 6,8-difluoro derivative of cyclindole.^[2]

References

↑ Wood PL, McQuade PS (1984). "Ciclindole and flucindole: novel tetrahydrocarbazolamine neuroleptics". Progress in Neuro-psychopharmacology & Biological Psychiatry 8 (4-6): 773–7. PMID 6152347.
↑ Edelson J, Benziger DP (1980). "Disposition of a series of tetrahydrocarbazoles". Drug Metabolism Reviews 11 (2): 263–89. doi:10.3109/03602538008994027. PMID 7011760.

Antipsychotics (neuroleptics) (N05A)

Typical

Benzamides: Levosulpiride; Nemonapride; Sulpiride; Sultopride; Tiapride; Veralipride

Butyrophenones: Azaperone; Benperidol; Bromperidol; Droperidol; Fluanisone; Haloperidol #; Lenperone; Moperone; Pipamperone; Spiperone; Timiperone; Trifluperidol

Diphenylbutylpiperidines: Clopimozide; Fluspirilene; Penfluridol; Pimozide

Phenothiazines: Acepromazine; Acetophenazine; Butaperazine; Carphenazine; Chloracizine; Chlorproethazine; Chlorpromazine; Cyamemazine; Dixyrazine; Fluacizine; Fluphenazine; Levomepromazine/Methotrimeprazine; Mesoridazine; Perazine; Pericyazine; Perphenazine; Piperacetazine; Pipotiazine; Prochlorperazine; Promazine; Promethazine; Propiomazine; Sulforidazine; Thiethylperazine; Thiopropazate; Thioproperazine; Thioridazine; Trifluoperazine; Triflupromazine

Thioxanthenes: Chlorprothixene; Clopenthixol; Flupentixol; Thiothixene; Zuclopenthixol

Tricyclics: Butaclamol; Fluotracen; Loxapine; Trimipramine

Others: Prothipendyl

Atypical

Benzamides: Amisulpride; Remoxipride‡

Butyrophenones: Cinuperone; Melperone; Setoperone

Benzo(iso)oxazole piperidines: Iloperidone; Ocaperidone; Paliperidone; Risperidone #

Benzo(iso)thiazole piperazines: Lurasidone; Perospirone; Revospirone; Tiospirone; Ziprasidone

Diphenylbutylpiperazines: Amperozide

Phenylpiperazines: Aripiprazole; Bifeprunox; Brexpiprazole^†; Elopiprazole; Umespirone

Tricyclics: Amoxapine; Asenapine; Carpipramine; Clocapramine; Clorotepine; Clotiapine; Clozapine #; Fluperlapine; Gevotroline; Metitepine; Mosapramine; NDMC; Olanzapine; Piquindone; Quetiapine; Tenilapine; Zotepine

Others: Blonanserin; Cariprazine; Molindone; Pimavanserin; Roxindole; Sarizotan; Sertindole; Spiramide; Zicronapine^†

Others

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

M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc (eval/thrp), drug (N5A/5B/5C/6A/6B/6D)

Dopaminergics

Receptor ligands

Agonists	Adamantanes: Amantadine Memantine Rimantadine; Aminotetralins: 7-OH-DPAT 8-OH-PBZI Rotigotine UH-232; Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959; Ergolines: Bromocriptine Cabergoline Dihydroergocryptine Epicriptine Lisuride LSD Pergolide; Dihydrexidine derivatives: 2-OH-NPA A-86,929 Ciladopa Dihydrexidine Dinapsoline Dinoxyline Doxanthrine; Others: A-68,930 A-77636 A-412,997 ABT-670 ABT-724 Aplindore Apomorphine Aripiprazole Bifeprunox BP-897 CY-208,243 Dizocilpine Etilevodopa Flibanserin Ketamine Melevodopa Modafinil Pardoprunox Phencyclidine PD-128,907 PD-168,077 PF-219,061 Piribedil Pramipexole Propylnorapomorphine Pukateine Quinagolide Quinelorane Quinpirole RDS-127 Ro10-5824 Ropinirole Rotigotine Roxindole Salvinorin A SKF-89,145 Sumanirole Terguride Umespirone WAY-100,635

Antagonists	Typical antipsychotics: Acepromazine Azaperone Benperidol Bromperidol Clopenthixol Chlorpromazine Chlorprothixene Droperidol Flupentixol Fluphenazine Fluspirilene Haloperidol Levosulpiride Loxapine Mesoridazine Methotrimeprazine Nemonapride Penfluridol Perazine Periciazine Perphenazine Pimozide Prochlorperazine Promazine Sulforidazine Sulpiride Sultopride Thioridazine Thiothixene Trifluoperazine Triflupromazine Trifluperidol Zuclopenthixol; Atypical antipsychotics: Amisulpride Asenapine Blonanserin Cariprazine Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Lurasidone Melperone Molindone Mosapramine Olanzapine Paliperidone Perospirone Piquindone Quetiapine Remoxipride Risperidone Sertindole Tiospirone Zicronapine Ziprasidone Zotepine; Antiemetics: AS-8112 Alizapride Bromopride Clebopride Domperidone Metoclopramide Thiethylperazine; Others: Amoxapine Buspirone Butaclamol Ecopipam EEDQ Eticlopride Fananserin Hydroxyzine L-745,870 Nafadotride Nuciferine PNU-99,194 Raclopride Sarizotan SB-277,011-A SCH-23,390 SKF-83,959 Sonepiprazole Spiperone Spiroxatrine Stepholidine Tetrahydropalmatine Tiapride UH-232 Yohimbine

Reuptake inhibitors

Plasmalemmal

DAT inhibitors

Piperazines: DBL-583
GBR-12,935
Nefazodone
Vanoxerine; Piperidines: BTCP
Desoxypipradrol
Dextromethylphenidate
Difemetorex
Ethylphenidate
Methylnaphthidate
Methylphenidate
Phencyclidine
Pipradrol; Pyrrolidines: Diphenylprolinol
MDPV
Naphyrone
Prolintane
Pyrovalerone; Tropanes: Altropane
Brasofensine
CFT
Cocaine
Dichloropane
Difluoropine
FE-β-CPPIT
FP-β-CPPIT
Ioflupane (¹²³I)
Iometopane
RTI-112
RTI-113
RTI-121
RTI-126
RTI-150
RTI-177
RTI-229
RTI-336
Tenocyclidine
Tesofensine
Troparil
Tropoxane
WF-11
WF-23
WF-31
WF-33; Others: Adrafinil
Armodafinil
Amfonelic acid
Amphetamine
Amineptine
Benzatropine
Bromantane
BTQ
BTS-74,398
Bupropion
Ciclazindol
Diclofensine
Dimethocaine
Diphenylpyraline
Dizocilpine
DOV-102,677
DOV-21,947
DOV-216,303
Etybenzatropine
EXP-561
Fencamine
Fencamfamine
Fezolamine
Fluorenol
GYKI-52,895
Indatraline
Ketamine
Lefetamine
Levophacetoperane
LR-5182
Manifaxine
Mazindol
Medifoxamine
Mesocarb
Modafinil
Nefopam
Nomifensine
NS-2359
O-2172
Pridefrine
Propylamphetamine
Radafaxine
SEP-225,289
SEP-227,162
Sertraline
Sibutramine
Tametraline
Tedatioxetine
Tripelennamine

Vesicular

VMAT inhibitors	Deserpidine Ibogaine Reserpine Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate
Fenmetramide
Morazone
Phendimetrazine
Phenmetrazine
Pseudophenmetrazine; Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, etc): 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
BOH
Benzphetamine
Buphedrone
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
D-Deprenyl
DMA
DMMA
Dimethylamphetamine
Dimethylcathinone
Ephedrine
Ethcathinone
EBDB
Ethylone
Etilamfetamine
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
Hydroxyamphetamine
Iofetamine
Lophophine
Mefenorex
Mephedrone
Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
Methcathinone
Methedrone
MMDA
MMDMA
MBDB
MDA
MDEA
MDMA
MDMPEA
MDOH
MDPEA
Methylone
Ortetamine
pBA
pCA
pIA
Pholedrine
Phenethylamine
Pholedrine
Phenpromethamine
Prenylamine
Propylamphetamine
Pseudoephedrine
Tiflorex
Tyramine
Xylopropamine
Zylofuramine; Piperazines: 2C-B-BZP
BZP
MBZP
MDBZP
MeOPP; Others: 2-ADN
2-AI
2-AT
4-BP
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
IAP
Indanorex
Isometheptene
Methylhexanamine
Naphthylisopropylamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane

Allosteric modulators

Quinazolinamines: SoRI-9804 SoRI-20040 SoRI-20041

Enzyme inhibitors

Anabolism

PAH inhibitors	3,4-Dihydroxystyrene

TH inhibitors	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD/DDC inhibitors	Benserazide Carbidopa DFMD Genistein Methyldopa

Catabolism

MAO inhibitors	Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine; MAO-A selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline Eprobemide Esuprone Harmala alkaloids Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B selective: D-Deprenyl Ethanol L-Deprenyl (Selegiline) Ladostigil Lazabemide Milacemide Nicotine Pargyline Rasagiline Safinamide

COMT inhibitors	Entacapone Nitecapone Tolcapone

DBH inhibitors	Disulfiram Dopastin Fusaric acid Nepicastat Tropolone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa)

Cofactors	Ferrous iron (Fe²⁺) Tetrahydrobiopterin Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal phosphate) Vitamin B₉ (Folic acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Others	Activity enhancers: BPAP * PPAP; Toxins: 6-OHDA; Steroids: Anabolic-androgenic steroids

List of dopaminergic drugs

v t e Tricyclics

Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene

Antidepressants	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine/Balipramine Desipramine 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 Nortriptyline Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline/Teciptiline Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine

Antihistamines	Alimemazine Azatadine Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium

Antipsychotics	Acetophenazine Amoxapine Asenapine Butaclamol Butaperazine Carphenazine Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepin 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

Others	Adosopine Aminopromazine Atiprosin Beloxepin Carbamazepine Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Eslicarbazepine acetate Etazepine Licarbazepine Methylene Blue Monatepil Nuvenzepine Oxcarbazepine Oxitriptyline Perlapine Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Rispenzepine Serazapine Siltenzepine Telenzepine Tipindole Tropatepine Zolenzepine

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Flucindole

See also

References