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| Other names | Lu 19-005 |
| Routes of administration | By mouth |
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| Formula | C16H15Cl2N |
| Molar mass | 292.20 g·mol−1 |
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Indatraline hydrochloride (Lu 19-005) is anantidepressive agent andnon-selectivemonoamine transporter inhibitor that blocks thereuptake ofdopamine,norepinephrine, andserotonin with similar efficacy tococaine.[1] This compound may be used to treatcocaine addictions as its effects have a slower onset and a longer duration than those of cocaine.[2] Indatraline has been shown to block the action ofmethamphetamine andMDMA in laboratory experiments.[3]
Indatraline isN-alkylated at the amino group, making it possible to slow the onset of action, so that it is not untilN-demethylation occurs that the molecules become active.N-methylindatraline has a longer duration than indatraline because norindatraline is inactive, whereas demethylatingN-methylindatraline does not terminate the actions of the parent compound.[citation needed]
Effects ofN-dimethylindatraline start about 20–30 minutes after administration; it takes a longer time for this chemical to absorb into the body than cocaine.[4]
Two main routes have been reported. The first route was reported by Bøgesø and co-workers.[5]
The other has been adapted to scale-up:[6]
Another method involves the contraction of a dihydronaphthalene (6–6 fused system) to form the 6–5 indane skeleton.[7]
Routes based on1-indanone-type intermediates are not as simple as a direct reduction of animine oroxime. The undesirable cis diastereomers are formed instead of the desirable trans isomers. This adds an extra step to the synthetic route. First, the ketones are reduced to mostly cis alcohols. Second, the cis alcohols are converted to the corresponding mesylates, conserving stereochemistry. Third, the mesylates can then be reacted, e.g. with,N-methylbenzylamine, causing aWalden inversion (SN2). Finally, the removal of the benzyl affords the product as a racemic mixture.[citation needed]
