Dixyrazine

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title: "Dixyrazine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hydroxyethyl-compounds", "dopamine-antagonists", "ethers", "h1-receptor-antagonists", "phenothiazines", "piperazines", "typical-antipsychotics", "ethanolamines"] topic_path: "general/hydroxyethyl-compounds" source: "https://en.wikipedia.org/wiki/Dixyrazine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | CASNo=2470-73-7 | PubChem=17182 | UNII_Ref = | UNII = 7H368W3AYC | ChemSpiderID_Ref = | 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 = | 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 = | StdInChIKey = MSYUMPGNGDNTIQ-UHFFFAOYSA-N | KEGG_Ref = | KEGG = D07865 |Section2={{Chembox Properties | Formula=C24H33N3O2S | MolarMass=427.60272 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section6={{Chembox Pharmacology | ATCCode_prefix = N05 | ATCCode_suffix = AB01 |Section7={{Chembox Legal status | legal_AU = | legal_BR = C1 | legal_BR_comment = | legal_US = | legal_UK = | legal_UN = |Section8={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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. 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

::figure[src="https://upload.wikimedia.org/wikipedia/commons/c/c6/Dixyrazine_synthesis.svg" caption="Synthesis of dixyrazine"] ::

Sodamide alkylation of phenothiazine (1) with 1-bromo-3-chloro-2-methylpropane (2) gives 10-(3-Chloro-2-methylpropyl)phenothiazine (3). 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

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. J. Elks. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  3. [https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0132 Thieme]
  4. Henri Morren, {{Cite patent. GB861420 (1961).

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hydroxyethyl-compoundsdopamine-antagonistsethersh1-receptor-antagonistsphenothiazinespiperazinestypical-antipsychoticsethanolamines