Homofenazine Explained

Synonyms:HFZ[1]
Tradename:Pasaden,[2] [3] Oldagen (in Argentina)[4] [5]
Atc Prefix:N05A
Legal Br:C1
Legal Br Comment:[6]
Cas Number:3833-99-6
Pubchem:19687
Chemspiderid:18545
Unii:PEL7G6VRZ2
Chebi:59071
Chembl:2105000
C:23
H:28
F:3
N:3
O:1
S:1
Smiles:C1CN(CCN(C1)CCO)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F
Stdinchi: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
Stdinchikey:LOHNHQLZFYCAEQ-UHFFFAOYSA-N
Boiling Point:230-240
Boiling Notes:[7]

Homofenazine is an antipsychotic drug of the phenothiazines class.[1] It was synthesized by Wilhelm Schuler and colleagues at Degussa.[8] [9] In 1966, it was released in Belgium under the brand name Pasaden.[2] At some point, it was quietly discontinued and is no longer marketed.

Synthesis

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).

Notes and References

  1. Book: Martindale: the complete drug reference . 2007 . Pharmaceutical Press . 978-0-85369-687-2 . London; Chicago . 899 . en . 1176310249.
  2. Book: 1991 Drugs available abroad: a guide to therapeutic drugs available and approved outside the U.S. . Schlesser JL . 1990 . Detroit : Gale Research . 978-0-8103-7177-4 . 107 . 1348900780.
  3. News: 1986-11-05 . Substâncias e remédios sob controle . pt-br . Substances and drugs under control . 14 . . live . 2023-08-08 . https://web.archive.org/web/20230808230340/https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf . 2023-08-08.
  4. Book: [{{google books|plainurl=y|id=5GpcTQD_L2oC|page=1501}} Index Nominum 2000: International Drug Directory ]. 2000 . Taylor & Francis . 9783887630751 . 17 . 2000 . 1499.
  5. Book: Sitting, Marshall . Pharmaceutical Manufacturing Encyclopedia (Vols 1&2, 2nd Ed) . 1988 . Noyes Publications . 0-8155-1144-2 . 2 . Westwood, NJ . 769 . en . 87-31547 . 52233518.
  6. Web site: Anvisa . Brazilian Health Regulatory Agency . 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. live . 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 . 2023-08-03 . 2023-08-03 . . pt-BR . 2023-04-04.
  7. Book: [{{google books|plainurl=y|id=0vXTBwAAQBAJ|page=635}} Dictionary of Drugs ]. 1990 . Springer US . 978-1-4757-2087-7 . Elks J, Ganellin CR . Boston, MA . 635 . en . 10.1007/978-1-4757-2085-3 .
  8. Book: The Merck index : an encyclopedia of chemicals, drugs, and biologicals . 1996 . Whitehouse Station, NJ : Merck . 978-0-911910-12-4 . 1285743402 . 810.
  9. US . 3040043 . Schuler et al. . patent . 3-trifluoromethyl-10-[3'-(4"-(2"'-hydroxy ethyl)-homopiperazino)-propyl]-phenothiazine and 3-trifluoromethyl-10-[3'-(4"-(2"'-acetoxyethyl)-homopiperazino)-propyl]-phenothiazine . 1962-06-19 . 1962-06-19 . 1960-03-14 . Degussa. .

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