Homofenazine

For the current use of the Pasaden brand, see Etizolam.

Homofenazine is an antipsychotic drug of the phenothiazines class.^[5] It was synthesized by Wilhelm Schuler and colleagues at Degussa.^[8][9] In 1966, it was released in Belgium under the brand name Pasaden.^[1] At some point, it was quietly discontinued and is no longer marketed.^{[citation needed]}

Homofenazine

Clinical data
Trade names	Pasaden,[1][2] Oldagen (in Argentina)[3][4]
Other names	HFZ[5]
ATC code	N05A
Legal status
Legal status	BR: Class C1 (Other controlled substances)[6]
Identifiers
CAS Number	3833-99-6 Y
PubChem CID	19687
ChemSpider	18545 Y
UNII	PEL7G6VRZ2
ChEBI	CHEBI:59071 Y
ChEMBL	ChEMBL2105000 Y
CompTox Dashboard (EPA)	DTXSID30191697
Chemical and physical data
Formula	C23H28F3N3OS
Molar mass	451.55 g·mol−1
3D model (JSmol)	Interactive image
Boiling point	230–240 °C (446–464 °F) [7]
SMILES C1CN(CCN(C1)CCO)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F
InChI InChI=1S/C23H28F3N3OS/c24-23(25,26)18-7-8-22-20(17-18)29(19-5-1-2-6-21(19)31-22)12-4-11-27-9-3-10-28(14-13-27)15-16-30/h1-2,5-8,17,30H,3-4,9-16H2 Y Key:LOHNHQLZFYCAEQ-UHFFFAOYSA-N Y

Synthesis

Thieme Patents (Ex 5&6):^[10][11]

The alkylation between 2-(Trifluoromethyl)Phenothiazine [92-30-8] (1) and 1-(3-bromopropyl)-1,4-diazepane (2) led to 10-[3-(1,4-diazepan-1-yl)propyl]-2-(trifluoromethyl)phenothiazine, CID:110174391 (3). Further alkylation with 2-Chloroethanol [107-07-3] (4) completed the synthesis of homofenazine (5).