Dixyrazine: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 449870181

| ImageFile=Dixyrazine.svg

| ImageSize = 280

| IUPACName=(''RS'')-2-[2-[4-(2-methyl-3-phenothiazin-10-ylpropyl)piperazin-1-yl]ethoxy]ethanol

| OtherNames= UCB-3412

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=2470-73-7

| PubChem=17182

| UNII_Ref = {{fdacite|correct|FDA}}

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 16265

| EINECS = 219-591-3

| 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

| Formula=C₂₄H₃₃N₃O₂S

| MolarMass=427.60272 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

|Section6={{Chembox Pharmacology

| ATCCode_prefix = N05

| ATCCode_suffix = AB01

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|Section7={{Chembox Legal status

| legal_AU =

| legal_BR = C1

| legal_BR_comment = <ref>{{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}}</ref>

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|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]].<ref name="Elks2014">{{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–}}</ref> It was first introduced in Germany in 1969. It is used as a neuroleptic, [[anxiolytic]], and antihistamine in doses between 12.5 and 75&nbsp;mg a day.

==Synthesis==

[[File:Dixyrazine synthesis.svg|thumb|center|500px|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0132 Thieme] Patent:<ref>Henri Morren, {{Cite patent|GB861420}} (1961).</ref>]]

Sodamide alkylation of [[phenothiazine]] ('''1''') with 1-bromo-3-chloro-2-methylpropane [6974-77-2] ('''2''') gives 10-(3-Chloro-2-methylpropyl)phenothiazine, [https://pubchem.ncbi.nlm.nih.gov/compound/12299119 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==

{{Reflist|2}}

{{Antipsychotics}}

{{Dopamine receptor modulators}}

{{Histamine receptor modulators}}

[[Category:Primary alcohols]]

[[Category:Dopamine antagonists]]

[[Category:Ethers]]

[[Category:H1 receptor antagonists]]

[[Category:Typical antipsychotics]]

[[Category:Ethanolamines]]

{{Nervous-system-drug-stub}}