Chemistry:Butaperazine

Short description: Typical antipsychotic

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 Y
PubChem CID	12598
DrugBank	DB13213
ChemSpider	12078 Y
UNII	TXP4T9106S
KEGG	D02642
ChEBI	CHEBI:135663
ChEMBL	ChEMBL1697826
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 Y Key:DVLBYTMYSMAKHP-UHFFFAOYSA-N Y
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Butaperazine (Repoise, Tyrylen) is a typical antipsychotic of the phenothiazine class. It was approved in 1967, and possibly discontinued in the 1980s.

Synthesis

Patent:

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.

See also

• Typical antipsychotic
• Phenothiazine