Etymemazine

Etymemazine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	none;
Identifiers
	IUPAC name 3-(2-ethylphenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine;
CAS Number	523-54-6; HCl: 3737-33-5 ;
PubChem CID	71823;
ChemSpider	64847;
UNII	861J4K81C7; HCl: A7002E7T2Z ;
ChEMBL	ChEMBL1967567;
CompTox Dashboard (EPA)	DTXSID0046935 ;
Chemical and physical data
Formula	C20H26N2S
Molar mass	326.50 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C=C3)=CC2=C3SC1=CC=CC=C1N2CC(C)CN(C)C;
	InChI InChI=1S/C20H26N2S/c1-5-16-10-11-20-18(12-16)22(14-15(2)13-21(3)4)17-8-6-7-9-19(17)23-20/h6-12,15H,5,13-14H2,1-4H3; Key:USKHCLAXJXCWMO-UHFFFAOYSA-N;
	(verify)

Etymemazine is an antipsychotic, antihistamine and anticholinergic drug of the phenothiazine chemical class, structurally related to cyamemazine and methotrimeprazine.^[1]

Synthesis

Sodamide Sn2 alkylation between 2-ethylphenothiazine [61852-27-5] (1) and 1-dimethylamino-2-methyl-3-chloropropane [23349-86-2] (2) furnishes the Etymemazine (3).

References

^ Milne GW (2002). "Etymemazine". Drugs: Synonyms and Properties (2nd ed.). Aldershot, Hampshire, England: Ashgate. p. 3945. ISBN 978-0-566-08491-1.
^ Anon., GB 789703 (1958 to Rhone Poulenc Sa).
^ Robert Michel Jacob, et al. U.S. patent 2,837,518 (1956 to Rhone Poulenc Sa).

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[1] Milne GW (2002). "Etymemazine". Drugs: Synonyms and Properties (2nd ed.). Aldershot, Hampshire, England: Ashgate. p. 3945. ISBN 978-0-566-08491-1.

[2] Anon., GB 789703 (1958 to Rhone Poulenc Sa).

[3] Robert Michel Jacob, et al. U.S. patent 2,837,518 (1956 to Rhone Poulenc Sa).

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[2]

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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