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Dixyrazine

From Wikipedia, the free encyclopedia
Dixyrazine
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 InfoCard100.017.811Edit 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 mass427.60272 g/mol
Pharmacology
N05AB01 (WHO)
Legal status
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Dixyrazine, also known asdixypazin (oxalate), sold under the brand namesAnsiolene,Esocalm,Esucos,Metronal, andRoscal, is atypical antipsychotic of thephenothiazine group described as aneuroleptic andantihistamine.[2] 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

[edit]
Synthesis of dixyrazine

Sodamide alkylation ofphenothiazine (1) with 1-bromo-3-chloro-2-methylpropane (2) gives 10-(3-Chloro-2-methylpropyl)phenothiazine (3).[3][4] 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

[edit]
  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
  2. ^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.
  3. ^Thieme
  4. ^Henri Morren,GB861420  (1961).
Typical
Disputed
Atypical
Others
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
Retrieved from "https://en.wikipedia.org/w/index.php?title=Dixyrazine&oldid=1285392189"
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