en Butaperazine

Butaperazine
Clinical data
ATC code	N05AB09 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances);
Identifiers
	IUPAC name 1-[10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazin-2-yl]butan-1-one;
CAS Number	653-03-2 ;
PubChem CID	12598;
DrugBank	DB13213;
ChemSpider	12078 ;
UNII	TXP4T9106S;
KEGG	D02642;
ChEBI	CHEBI:135663;
ChEMBL	ChEMBL1697826;
CompTox Dashboard (EPA)	DTXSID1022712 ;
ECHA InfoCard	100.010.450
Chemical and physical data
Formula	C24H31N3OS
Molar mass	409.59 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(C)CC4)CCC;
	InChI InChI=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 ; Key:DVLBYTMYSMAKHP-UHFFFAOYSA-N ;
	(verify)

Butaperazine (Repoise, Tyrylen) is a typical antipsychotic of the phenothiazine class.^[2] It was approved in 1967, and possibly discontinued in the 1980s.

Synthesis

2-Butyrylphenothiazine [25244-91-1] (1) is the requisite starting material for carrying out the procedure. It is prepared in a manner that is synonymous with the method used in the propiomazine and propiopromazine already discussed. The 1-(γ-chloropropyl)-4-methylpiperazine [104-16-5] (2) is prepared in the conventional way from alkylating 1-methylpiperazine and 1-Bromo-3-chloropropane. Sodamide is used to extract the 10-H thereby facilitating the nucleophilic substitution reaction. And completing the instalment of the sidechain.

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.
^ "Evaluation of a new antipsychotic agent. Butaperazine maleate (repoise maleate)". JAMA. 206 (10): 2307–8. December 1968. doi:10.1001/jama.206.10.2307. PMID 4386884.
^ Dr Ulrich Hoerlein, Dr Klaus-Heinz Risse, Dr Wolfgang Wirth, DE 1120451 (1961 to Bayer Ag).

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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.

[pmid4386884-2] "Evaluation of a new antipsychotic agent. Butaperazine maleate (repoise maleate)". JAMA. 206 (10): 2307–8. December 1968. doi:10.1001/jama.206.10.2307. PMID 4386884.

[3] Dr Ulrich Hoerlein, Dr Klaus-Heinz Risse, Dr Wolfgang Wirth, DE 1120451 (1961 to Bayer Ag).

[1]

[2]

[3]

Butaperazine

Synthesis

See also

References