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| Formula | C17H17Cl2NO |
| Molar mass | 322.23 g·mol−1 |
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Diclofensine (Ro 8-4650) was developed byHoffmann-La Roche in the 1970s[1] in the search for a new antidepressant. It was found that the (S)-isomer was responsible for activity.[2] Diclofensine is astimulant drug which acts as atriple monoamine reuptake inhibitor,[3][4] primarily inhibiting the reuptake of dopamine[5] and norepinephrine,[6] with affinities (Ki) of 16.8 nM, 15.7 nM, and 51 nM forDAT,NET, andSERT (dopamine, norepinephrine and serotonin transporters), respectively.[7] It was found to be an effectiveantidepressant in human trials,[8][9][10] with relatively few side effects,[11] but was ultimately dropped from clinical development, possibly due to concerns about itsabuse potential.[12][13]
Diclofensine is chemically atetrahydroisoquinoline (THIQ) derivative, as isnomifensine.
The condensation of m-anisaldehyde [591-31-1] (1) with methylamine gives N-methyl-3-methoxybenzenemethanimine [16928-30-6]. Reduction of this Schiff-base intermediate with sodium borohydride gives (3-methoxybenzyl)methylamine [41789-95-1] (2). Alkylation of this with 3,4-dichlorophenacylbromide [2632-10-2] (3) would giveCID:59580342 (4). Reduction of the benzoyl ketone withsodium borohydride gives the alcohol [802051-24-7] (5). Acid catalyzed intramolecular cyclization then completes the synthesis of the 4-aryl-THIQ derivative, diclofensine (6).
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