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Tropatepine

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Chemical compound

Pharmaceutical compound

Tropatepine
Clinical data

Trade names	Lepticur
AHFS/Drugs.com	International Drug Names
ATC code	N04AA12 (WHO)
Identifiers
IUPAC name (1S,5S)-3-dibenzo[b,e]thiepin-11(6H)-ylidene-8-methyl-8-azabicyclo[3.2.1]octane
CAS Number	27574-24-9
PubChemCID	198068
ChemSpider	171431^Y
UNII	C27HY5RFU5
KEGG	D07303^Y
CompTox Dashboard(EPA)	DTXSID70865380
Chemical and physical data
Formula	C₂₂H₂₃NS
Molar mass	333.49 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES S3c1ccccc1/C(c2c(cccc2)C3)=C5/CC4N(C)C(CC4)C5
InChI InChI=1S/C22H23NS/c1-23-17-10-11-18(23)13-16(12-17)22-19-7-3-2-6-15(19)14-24-21-9-5-4-8-20(21)22/h2-9,17-18H,10-14H2,1H3^Y Key:JOQKFRLFXDPXHX-UHFFFAOYSA-N^Y
(verify)

Tropatepine (brand nameLepticur) is ananticholinergic used as anantiparkinsonian agent.^[1]

Synthesis

[edit]

Tropatepine can be synthesized from 3-chlorotropane (1).^[2] A Grignard reaction between 3-chlorotropane and dibenzo[b,e]thiepin-11(6H)-one (2) followed bydehydration to the olefin produces tropatepine (3).

References

[edit]

^Celsis P, Montastruc JL, Rascol O, Senard JM, Marc-Vergnes JP, Rascol A (July 1989)."Effect of tropatepine, an anticholinergic drug, on regional cerebral blood flow in patients with Parkinson's disease".Journal of Neurology, Neurosurgery, and Psychiatry.52 (7):917–8.doi:10.1136/jnnp.52.7.917.PMC 1031949.PMID 2769291.
^DE1952206 idem J Boissier, R Ratouis,U.S. patent 3,725,415 (1973 to Ind Pour La Fab Antibiotiques).

Antiparkinson agents (N04)

Dopaminergics

DA precursors	Levodopa^# (+benserazide,+carbidopa,+carbidopa/entacapone) Foslevodopa (+foscarbodipa) Melevodopa (+carbidopa)
DA receptor agonists	Ergoline:Bromocriptine Cabergoline Dihydroergocryptine Lisuride Pergolide Non-ergoline:Apomorphine Piribedil Pramipexole Ropinirole Rotigotine Talipexole
MAO-B inhibitors	Rasagiline Safinamide Selegiline
COMT inhibitors	Entacapone Opicapone Tolcapone
AAAD inhibitors	Benserazide (+levodopa) Carbidopa^# (+carbidopa,+melevodopa,+carbidopa/entacapone) Foscarbidopa (+foslevodopa)

Anticholinergics

Others

Adamantanes (e.g.,amantadine,memantine,rimantadine)
Adenosine receptor antagonists (e.g.,caffeine,istradefylline)
Budipine

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^‡Withdrawn from market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

Muscarinic acetylcholine receptor modulators

mAChRsTooltip Muscarinic acetylcholine receptors

Agonists

Antagonists

Precursors
(andprodrugs)

See also: Receptor/signaling modulators; Nicotinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

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 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 Pinadoline Pitrazepin Pizotifen Serazapine Tipindole

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