homofenazine
{{Short description|Antipsychotic medication}}
{{For|the current use of the Pasaden brand|Etizolam}}
{{Infobox drug
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| image = Homofenazine.svg
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| tradename = Pasaden,{{Cite book |url=https://archive.org/details/1991drugsavailab0000unse/page/106/mode/2up?q=Homofenazine |title=1991 Drugs available abroad: a guide to therapeutic drugs available and approved outside the U.S. |vauthors=Schlesser JL |date=1990 |publisher=Detroit : Gale Research |isbn=978-0-8103-7177-4 |pages=107 |oclc=1348900780}}{{Cite news |date=1986-11-05 |title=Substâncias e remédios sob controle |language=pt-br |trans-title=Substances and drugs under control |pages=14 |work=Jornal do Brasil |url=https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |url-status=live |access-date=2023-08-08 |archive-url=https://web.archive.org/web/20230808230340/https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |archive-date=2023-08-08}} Oldagen (in Argentina){{Cite book |url={{google books|plainurl=y|id=5GpcTQD_L2oC|page=1501}} |title=Index Nominum 2000: International Drug Directory |date=2000 |publisher=Taylor & Francis |isbn=9783887630751 |edition=17 |publication-date=2000 |pages=1499}}{{Cite book |last=Sitting |first=Marshall |url=https://archive.org/details/Pharmaceutical_Manufacturing_Encyclopedia_Vols_12_2nd_Ed/page/769 |title=Pharmaceutical Manufacturing Encyclopedia (Vols 1&2, 2nd Ed) |date=1988 |publisher=Noyes Publications |isbn=0-8155-1144-2 |edition=2 |location=Westwood, NJ |pages=769 |language=en |lccn=87-31547 |oclc=52233518}}
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| ATC_prefix = N05A
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| 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=2023-08-03 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3833-99-6
| PubChem = 19687
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18545
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| UNII = PEL7G6VRZ2
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| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 59071
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| 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_Ref = {{stdinchicite|correct|chemspider}}
| 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LOHNHQLZFYCAEQ-UHFFFAOYSA-N
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| boiling_point = 230-240
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Homofenazine is an antipsychotic drug of the phenothiazines class. It was synthesized by Wilhelm Schuler and colleagues at Degussa.{{Cite book |url=https://archive.org/details/merckindexencycl0000unse/page/810/mode/2up |title=The Merck index : an encyclopedia of chemicals, drugs, and biologicals |date=1996 |publisher=Whitehouse Station, NJ : Merck |isbn=978-0-911910-12-4 |oclc=1285743402 |pages=810}}{{cite patent |country= US |number= 3040043 |inventor= Schuler et al. |status= patent |title= 3-trifluoromethyl-10-[3'-(4"-(2"'-hydroxy ethyl)-homopiperazino)-propyl]-phenothiazine and 3-trifluoromethyl-10-[3'-(4"-(2"'-acetoxyethyl)-homopiperazino)-propyl]-phenothiazine |pubdate=1962-06-19 |gdate=1962-06-19 |fdate=1960-03-14 |assign1= Degussa}}. In 1966, it was released in Belgium under the brand name Pasaden. At some point, it was quietly discontinued and is no longer marketed.{{citation needed|date=August 2023}}
Synthesis
File:Homofenazine synthesis.svg
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, [https://pubchem.ncbi.nlm.nih.gov/compound/110174391 CID:110174391] (3). Further alkylation with 2-Chloroethanol [107-07-3] (4) completed the synthesis of homofenazine (5).