2-[2-(dimethylamino)ethoxy]-N-tricyclo[3.3.1.13,7]dec-1-ylacetamide monohydrochloride manufacturers
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| | 2-[2-(dimethylamino)ethoxy]-N-tricyclo[3.3.1.13,7]dec-1-ylacetamide monohydrochloride Basic information |
| | 2-[2-(dimethylamino)ethoxy]-N-tricyclo[3.3.1.13,7]dec-1-ylacetamide monohydrochloride Chemical Properties |
| Melting point | 157-158° | | form | Solid | | color | White to off-white |
| Toxicity | LD50 orally in rats: 630 mg/kg; i.v. in mice: 71.0 mg/kg (Peteri, Sterner) |
| | 2-[2-(dimethylamino)ethoxy]-N-tricyclo[3.3.1.13,7]dec-1-ylacetamide monohydrochloride Usage And Synthesis |
| Originator | Viru-Merz,Merz,W. Germany,1973 | | Uses | Tromantadine hydrochloride, an Amantadine derivative with antiherpetic activity, inhibits herpes simplex virus type 1 (HSV-1) and HSV-2 replication[1]. | | Manufacturing Process | Adamantane is first reacted with chloroacetyl chloride to give
chloroacetylaminoadamantane.
2.3 g Na (0.1 g-atom) were dissolved in 75 ml dimethylamino-ethanol. Then
the excess alcohol was distilled off completely and the sodium salt developed
was dried in a vacuum. After drying, the salt was dissolved in about 200 ml
xylene. To thissolution.22.8 g (0.1 mol) chloroacetylaminoadamantane were added, heated for 10 hours under reflux in a 250-ml round-bottomed flask
with a reflux cooler, and the sodium chloride developed subsequently filtered
off.
Next the xylene was distilled away, the liquid residue dissolved in about 80 ml
carbon tetrachloride and the hydrochloride precipitated through introduction of
hydrochloric acid gas. The hydrochloride was dissolved in about 100 ml
acetone and the solvent subsequently distilled away, whereby excess
hydrochloric acid passed over with it. This operation was repeated until no
excess acid was present.
A large excess of petroleum ether was added in a 500 ml three-necked flask
provided with a stirrer and reflux cooler, to a concentrated acetonic solution of
the hydrochloride and stirred for at least 1 hour, whereby the desired
substance was deposited in a crystalline form. Finally, the substance was
filtered away and dried in a desiccator. 14 g of the substance (15% of theory)
were obtained. | | Therapeutic Function | Antiviral | | IC 50 | HSV-1; HSV-2 | | References | [1] Rosenthal KS, et al. Tromantadine: inhibitor of early and late events in herpes simplex virus replication. Antimicrob Agents Chemother. 1982 Dec;22(6):1031-6. DOI:10.1128/AAC.22.6.1031 |
| | 2-[2-(dimethylamino)ethoxy]-N-tricyclo[3.3.1.13,7]dec-1-ylacetamide monohydrochloride Preparation Products And Raw materials |
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