Dixyrazine
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 449870181
| ImageFile=Dixyrazine.svg
| ImageClass = skin-invert-image
| ImageSize = 280
| IUPACName=(RS)-2-[2-[4-(2-methyl-3-phenothiazin-10-ylpropyl)piperazin-1-yl]ethoxy]ethanol
| OtherNames= UCB-3412
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=2470-73-7
| PubChem=17182
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7H368W3AYC
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 16265
| EINECS = 219-591-3
| SMILES=CC(CN1CCN(CC1)CCOCCO)CN2C3=CC=CC=C3SC4=CC=CC=C42
| InChI = 1/C24H33N3O2S/c1-20(18-26-12-10-25(11-13-26)14-16-29-17-15-28)19-27-21-6-2-4-8-23(21)30-24-9-5-3-7-22(24)27/h2-9,20,28H,10-19H2,1H3
| InChIKey = MSYUMPGNGDNTIQ-UHFFFAOYAI
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C24H33N3O2S/c1-20(18-26-12-10-25(11-13-26)14-16-29-17-15-28)19-27-21-6-2-4-8-23(21)30-24-9-5-3-7-22(24)27/h2-9,20,28H,10-19H2,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MSYUMPGNGDNTIQ-UHFFFAOYSA-N
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D07865
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|Section2={{Chembox Properties
| Formula=C24H33N3O2S
| MolarMass=427.60272 g/mol
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|Section6={{Chembox Pharmacology
| ATCCode_prefix = N05
| ATCCode_suffix = AB01
}}
|Section7={{Chembox Legal status
| legal_AU =
| legal_BR = C1
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}
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|Section8={{Chembox Hazards
| MainHazards=
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Dixyrazine, also known as dixypazin (oxalate), sold under the brand names Ansiolene, Esocalm, Esucos, Metronal, and Roscal, is a typical antipsychotic of the phenothiazine group described as a neuroleptic and antihistamine.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA462|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=462–}} It was first introduced in Germany in 1969. It is used as a neuroleptic, anxiolytic, and antihistamine in doses between 12.5 and 75 mg a day.
Synthesis
Sodamide alkylation of phenothiazine (1) with 1-bromo-3-chloro-2-methylpropane (2) gives 10-(3-Chloro-2-methylpropyl)phenothiazine (3).[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0132 Thieme]Henri Morren, {{Cite patent|GB861420}} (1961). Completion of the sidechain by alkylation with 1-[2-(2-hydroxyethoxy)ethyl]piperazine (4) and displacement of the halogen completes the synthesis of dixyrazine (5).
References
{{Reflist}}
{{Antipsychotics}}
{{Dopamine receptor modulators}}
{{Histamine receptor modulators}}
Category:Hydroxyethyl compounds
Category:H1 receptor antagonists