Butaperazine
{{short description|Typical antipsychotic}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 444527276
| IUPAC_name = 1-[10-[3-(4-Methylpiperazin-1-yl)propyl]phenothiazin-2-yl]butan-1-one
| image = Butaperazine.svg
| image_class = skin-invert-image
| width = 250
| tradename =
| legal_AU =
| legal_BR = C1
| legal_BR_comment = {{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}}
| legal_CA =
| legal_DE =
| legal_NZ =
| legal_UK =
| legal_US =
| legal_EU =
| legal_UN =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 653-03-2
| PubChem = 12598
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12078
| KEGG = D02642
| ChEBI = 135663
| ChEMBL = 1697826
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TXP4T9106S
| ATC_prefix = N05
| ATC_suffix = AB09
| DrugBank = DB13213
| C=24 | H=31 | N=3 | O=1 | S=1
| smiles = O=C(c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(C)CC4)CCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H31N3OS/c1-3-7-22(28)19-10-11-24-21(18-19)27(20-8-4-5-9-23(20)29-24)13-6-12-26-16-14-25(2)15-17-26/h4-5,8-11,18H,3,6-7,12-17H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DVLBYTMYSMAKHP-UHFFFAOYSA-N
}}
Butaperazine (Repoise, Tyrylen) is a typical antipsychotic of the phenothiazine class.{{cite journal | vauthors = | title = Evaluation of a new antipsychotic agent. Butaperazine maleate (repoise maleate) | journal = JAMA | volume = 206 | issue = 10 | pages = 2307–8 | date = December 1968 | pmid = 4386884 | doi = 10.1001/jama.206.10.2307 }} It was approved in 1967, and possibly discontinued in the 1980s.
Synthesis
File:Butaperazine synthesis.svg
Butaperazine can be synthesized starting from 2-butyrylphenothiazine (1).Dr Ulrich Hoerlein, Dr Klaus-Heinz Risse, Dr Wolfgang Wirth, {{Cite patent|DE|1120451}} (1961 to Bayer Ag). It is prepared in a manner that is comparable to the method used in the synthesis of propiomazine and propiopromazine.{{clarify|date=March 2025}} The phenothiazine is alkylated with 1-(γ-chloropropyl)-4-methylpiperazine (2), which is prepared in the conventional way by alkylating 1-methylpiperazine with 1-bromo-3-chloropropane.
See also
References
{{Reflist}}
{{Antipsychotics}}
{{Adrenergics}}
{{Cholinergics}}
{{Dopaminergics}}
{{Histaminergics}}
{{Tricyclics}}
Category:4-Methylpiperazin-1-yl compounds