:Dacemazine
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 460112476
| IUPAC_name = 2-dimethylamino-1-phenothiazin-10-ylethanone
| image = Dacemazine.svg
| width =
| tradename =
| routes_of_administration =
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 518-61-6
| ATC_prefix = none
| PubChem = 68846
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2107547
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62079
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 88D34UY0QI
| C=16 | H=16 | N=2 | O=1 | S=1
| smiles = O=C(N1c3c(Sc2c1cccc2)cccc3)CN(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HKUCYAHWPVLPFN-UHFFFAOYSA-N
}}
Dacemazine (INN, also known as Ahistan and Histantine){{cite book | vauthors = Triggle DJ, Ganellin CR, MacDonald F |title=Dictionary of Pharmacological Agents |publisher=Chapman & Hall/CRC |location=Boca Raton |year=1996 |volume=1 |pages=711 |isbn=0-412-46630-9 |url=https://books.google.com/books?id=DeX7jgInYFMC}} Retrieved on August 2, 2008 through Google Book Search. 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. It was also assessed as a possible anticancer drug.{{cite journal | vauthors = Karolyhazy G, Havas I, Jansco G, Kapas L, Sellei C | title = [The anticarcinogenic effect of dimethylaminoacetyl-phentiazide (ahistan)] | language = ro | journal = Kiserletes Orvostudomany | volume = 4 | issue = 4 | pages = 260–2 | date = August 1952 | pmid = 13023855 }}
Synthesis
Amide formation between phenothiazine (1) and chloroacetyl chloride (2) gives 10-(Chloroacetyl)-phenothiazine [786-50-5] (3). The subsequent displacement of the remaining halogen with dimethylamine (4) completes the synthesis of dacemazine (5).
References
{{Reflist|2}}
{{Cholinergics}}
{{Histaminergics}}
{{Tricyclics}}
Category:H1 receptor antagonists
{{respiratory-system-drug-stub}}