Gastrophenzine
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| Synonyms | gastrofenzin, AN5, DZO-200. |
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| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}} |
| Chemical and physical data | |
| Formula | C19H21ClN2O2 |
| Molar mass | 344.84 g·mol−1 |
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Gastrophenzine (AN5, DZO-200) is a Bulgarian antiulcerogenic drug. It is related to Nomifensine. AN5 possesses an antiulcer activity many times higher than that of ranitidine and cimetidine.[1]
A study found that gastrophenzine lacked genotoxicity and was non-mutagenic.[2]
By virtue of its dopaminergic properties, AN5 might also be indicated off-label for use in the treatment of either depression or Parkinson's disease.
Compare also to other aniline-containing urethane drugs: Bonnecor, Ethacizine and Moricizine.
Synthesis
The alkylation of N-Methyl-2-nitrobenzylamine [56222-08-3] (1) with 4-chlorostyrene oxide [2788-86-5] (2) affords N-(2-nitrobenzyl)-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol (3). The reduction of the nitro group with NaBH4/NiCl2 in boiling methanol gave N-(2-aminobenzyl)-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol [102436-79-3] (4). Urethane formation with ethyl chloroformate results in N-[2-(ethoxycarbonyl)amino]-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol (5). The latter is cyclodehydrated by means of conc. H2SO4 in dichloroethane to Gastrophenzine (6).
According to method B, the amino alcohol (4) is cyclodehydrated by conc. H2SO4 to 8-amino-4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline, PC14493695 (7). Urethane formation with ethyl chloroformate also gives Gastrophenzine.
References
- ↑ Ivanova N, Mondeshka D, Ivanov C, Angelova I, Terziyska S, Paskov V (1990). "A new class of antiulcer drugs. I. Antiulcer effect of AN5, a 4-phenyl-tetrahydroisoquinoline derivative, on different experimental models of ulcer in rats". Methods and Findings in Experimental and Clinical Pharmacology. 12 (6): 401–10. PMID 2087139.
- ↑ Mirkova E (1994). "[The genotoxicity and carcinogenic potential of gastrofenzin]". Eksperimentalna Meditsina I Morfologiia (in Bulgarian). 32 (3–4): 57–68. PMID 8857033.CS1 maint: Unrecognized language (link)
- ↑ Ivanova N, Angelova J, Mondeshka D, Ivanov C (1992). "Gastrophenzine: Antiulcer". Drugs of the Future. 17 (2): 104. doi:10.1358/dof.1992.017.02.164146.
- ↑ Ivanova N, Ivanov T, Mondeshka D, Berova N, Angelova I, Rakovska R, Bojadjiev S, Tancheva C, Tascheva D (January 1990). "[Synthesis, stereochemistry and anticonvulsant action of 4-phenyltetrahydroisoquinolines]". Archiv der Pharmazie (in German). 323 (1): 3–7. doi:10.1002/ardp.19903230103. PMID 2334267.CS1 maint: Unrecognized language (link)
- ↑ US 4537895, Deak G, Zara E, Gyorgy L, Fekete M, Doda M, Seregi A, Kanyicska B, Toth E, Horvath M, Manyai S, Gorgenyi F, Vaszovics G, "Isoquinoline derivatives", issued 27 August 1985, assigned to Egyt Gyogyszervegyeszeti Gyar
- ↑ Zára-Kaczián E, György L, Deák G, Seregi A, Dóda M (July 1986). "Synthesis and pharmacological evaluation of some new tetrahydroisoquinoline derivatives inhibiting dopamine uptake and/or possessing a dopaminomimetic property". Journal of Medicinal Chemistry. 29 (7): 1189–95. doi:10.1021/jm00157a012. PMID 3806569.
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