Tropatepine

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;
PubChem CID	198068;
ChemSpider	171431 ;
UNII	C27HY5RFU5;
KEGG	D07303 ;
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 ; Key:JOQKFRLFXDPXHX-UHFFFAOYSA-N ;
	(verify)

Tropatepine (brand name Lepticur) is an anticholinergic used as an antiparkinsonian agent.^[1]

Synthesis

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 by dehydration to the olefin produces tropatepine (3).

References

^ 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).

[1] 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.

[2] DE1952206 idem J Boissier, R Ratouis, U.S. patent 3,725,415 (1973 to Ind Pour La Fab Antibiotiques).

[1]

[2]

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 Butriptyline Cianopramine Ciclazindol Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) (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 Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene 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 Lurasidone 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 Rispenzepine
Anticholinergics	Profenamine Tropatepine
Others	Adosopine Aminopromazine Atiprosin Beloxepin Benzoctamine Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Fluradoline Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine Pipazethate P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Serazapine Siltenzepine Telenzepine Tipindole Zolenzepine

Tropatepine

Synthesis

See also

References

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