Dixyrazine

Dixyrazine
Names
	IUPAC name (RS)-2-[2-[4-(2-methyl-3-phenothiazin-10-ylpropyl)piperazin-1-yl]ethoxy]ethanol
	Other names UCB-3412
Identifiers
CAS Number	2470-73-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	16265 ;
ECHA InfoCard	100.017.811
EC Number	219-591-3;
KEGG	D07865 ;
PubChem CID	17182;
UNII	7H368W3AYC ;
CompTox Dashboard (EPA)	DTXSID10947639 ;
	InChI 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 Key: MSYUMPGNGDNTIQ-UHFFFAOYSA-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;
	SMILES CC(CN1CCN(CC1)CCOCCO)CN2C3=CC=CC=C3SC4=CC=CC=C42;
Properties
Chemical formula	C24H33N3O2S
Molar mass	427.60272 g/mol
Pharmacology
ATC code	N05AB01 (WHO)
Legal status	BR: Class C1 (Other controlled substances);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[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

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

^ 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. Retrieved 2023-08-16.
^ 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.
^ Henri Morren, GB861420 (1961).

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[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. Retrieved 2023-08-16.

[Elks2014-2] 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] Henri Morren, GB861420 (1961).

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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Muscarinic agonists: Xanomeline/trospium chloride Others/unknown: Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III