Dacemazine

Dacemazine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-dimethylamino-1-phenothiazin-10-ylethanone;
CAS Number	518-61-6 ;
PubChem CID	68846;
ChemSpider	62079 ;
UNII	88D34UY0QI;
ChEMBL	ChEMBL2107547 ;
CompTox Dashboard (EPA)	DTXSID70199733 ;
Chemical and physical data
Formula	C16H16N2OS
Molar mass	284.38 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N1c3c(Sc2c1cccc2)cccc3)CN(C)C;
	InChI InChI=1S/C16H16N2OS/c1-17(2)11-16(19)18-12-7-3-5-9-14(12)20-15-10-6-4-8-13(15)18/h3-10H,11H2,1-2H3 ; Key:HKUCYAHWPVLPFN-UHFFFAOYSA-N ;
	(what is this?) (verify)

Dacemazine (INN, also known as Ahistan and Histantine)^[1] is a phenothiazine derivative which acts as a histamine antagonist at the H₁ subtype. First described in 1951, it was never marketed as a drug on its own, although a combination of dacemazine and di-tert-butylnaphthalenesulfonate was sold as an antispasmodic and antitussive under the trade name Codopectyl.^[1] It was also assessed as a possible anticancer drug.^[2]

Synthesis

Amide formation between phenothiazine (1) and chloroacetyl chloride (2) gives 10-(chloroacetyl)-phenothiazine (3). The subsequent displacement of the remaining halogen with dimethylamine (4) completes the synthesis of dacemazine (5).

References

1 2 Triggle DJ, Ganellin CR, MacDonald F (1996). Dictionary of Pharmacological Agents. Vol. 1. Boca Raton: Chapman & Hall/CRC. p. 711. ISBN 978-0-412-46630-4.
↑ Karolyhazy G, Havas I, Jancso G, Kapas L, Sellei C (August 1952). "[The anticarcinogenic effect of dimethylaminoacetyl-phentiazide (ahistan)]". Kiserletes Orvostudomany (in Romanian). 4 (4): 260–262. PMID 13023855.
↑ Dahlbom R, Ekstrand T, Rubin I, Saluste E, Stjernholm R, Ehrensvärd G (1951). "10-Aminoacylphenothiazines. I. Aminoacetyl and Aminopropionyl Derivatives". Acta Chemica Scandinavica. 5: 102–114. doi:10.3891/acta.chem.scand.05-0102.
↑ Wassermann N, Ionescu M, Cuiban L, Panaiteslu T, Gheorghiu M, Arhip C (1959). "Syntheses of phenothiazine drugs". Revistade Chimie. 10. Bucharest, Romania: 81–85.
↑ Kano H, Makisumi Y (1957). "Phenothiazine derivatives. II. Synthesis of 10-(alkylaminoacetyl)phenothiazines". Shionogi Kenkyusho Nempo [Annual Report of Shionogi Research Laboratory] (in Japanese). 7: 511–516. Abstract in: Chem Abstr. 1958;52:10094.
↑ US 2694705, Cusic JW, "N-(Hydroxyalkylaminoalkanoyl)phenothiazines", issued 16 November 1954, assigned to G.D. Searle & Co.

[Triggle_1996-1] 1 2 Triggle DJ, Ganellin CR, MacDonald F (1996). Dictionary of Pharmacological Agents. Vol. 1. Boca Raton: Chapman & Hall/CRC. p. 711. ISBN 978-0-412-46630-4.

[pmid13023855-2] Karolyhazy G, Havas I, Jancso G, Kapas L, Sellei C (August 1952). "[The anticarcinogenic effect of dimethylaminoacetyl-phentiazide (ahistan)]". Kiserletes Orvostudomany (in Romanian). 4 (4): 260–262. PMID 13023855.

[3] Dahlbom R, Ekstrand T, Rubin I, Saluste E, Stjernholm R, Ehrensvärd G (1951). "10-Aminoacylphenothiazines. I. Aminoacetyl and Aminopropionyl Derivatives". Acta Chemica Scandinavica. 5: 102–114. doi:10.3891/acta.chem.scand.05-0102.

[4] Wassermann N, Ionescu M, Cuiban L, Panaiteslu T, Gheorghiu M, Arhip C (1959). "Syntheses of phenothiazine drugs". Revistade Chimie. 10. Bucharest, Romania: 81–85.

[5] Kano H, Makisumi Y (1957). "Phenothiazine derivatives. II. Synthesis of 10-(alkylaminoacetyl)phenothiazines". Shionogi Kenkyusho Nempo [Annual Report of Shionogi Research Laboratory] (in Japanese). 7: 511–516. Abstract in: Chem Abstr. 1958;52:10094.

[6] US 2694705, Cusic JW, "N-(Hydroxyalkylaminoalkanoyl)phenothiazines", issued 16 November 1954, assigned to G.D. Searle & Co.

[1]

[2]

[3]

[4]

[5]

[6]

v t e Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (a.k.a. TCAsTooltip tricyclic antidepressant)	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 Estianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Cidoxepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Dioxopromethazine 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 Carvotroline 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 Apadoline Atiprosin Benzoctamine Botiacrine Carvedilol Cyclobenzaprine Damotepine Elanzepine Fluradoline Methylene blue Monatepil Oxetorone Pipazethate P7C3 P7C3-A20 Pinadoline Pitrazepin Pizotifen Serazapine Tipindole