Dixyrazine
Dixyrazine.svg
Names
IUPAC name
(RS)-2-[2-[4-(2-methyl-3-phenothiazin-10-ylpropyl)piperazin-1-yl]ethoxy]ethanol
Other names
UCB-3412
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.811 Edit this at Wikidata
EC Number
  • 219-591-3
KEGG
UNII
  • InChI=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 ☒N
    Key: MSYUMPGNGDNTIQ-UHFFFAOYSA-N ☒N
  • 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
    Key: MSYUMPGNGDNTIQ-UHFFFAOYAI
  • CC(CN1CCN(CC1)CCOCCO)CN2C3=CC=CC=C3SC4=CC=CC=C42
Properties
C24H33N3O2S
Molar mass 427.60272 g/mol
Pharmacology
N05AB01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1] 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

Thieme Patent:[2]
Thieme Patent:[2]

Sodamide alkylation of phenothiazine (1) with 1-bromo-3-chloro-2-methylpropane [6974-77-2] (2) gives 10-(3-Chloro-2-methylpropyl)phenothiazine, CID:12299119 (3). Completion of the sidechain by alkylation with 1-[2-(2-Hydroxyethoxy) Ethyl]Piperazine [13349-82-1] (4) and displacement of the halogen completes the synthesis of Dixyrazine (5).

References

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 462–. ISBN 978-1-4757-2085-3.
  2. ^ Henri Morren, GB861420  (1961).