Selective serotonin reuptake inhibitors, 128 sumatriptan

Serotonin syndrome (sibutramine) The rare, but serious, constellation of symptoms also has been reported with the concomitant use of selective serotonin reuptake inhibitors and agents for migraine therapy (eg, sumatriptan, dihydroergotamine), certain opioids (eg, dextromethorphan, meperidine, pentazocine, fentanyl), lithium, or tryptophan. Because sibutramine inhibits serotonin reuptake, it should not be administered with other serotonergic agents. 

Sumatriptan should be avoided by patients taking selective serotonin reuptake inhibitors, monoamine oxidase inhibitors, moclobemide, St John s wort... 

Macor exploited this methodology to synthesize several antimigraine analogs of Sumatriptan, e.g. 307 [304], and homotryptamines as potent and selective serotonin reuptake inhibitors [305]. 

Macor also exploited the Mori-Ban indole synthesis to synthesize several anti-migraine analogues of sumatriptan and homo-tiyptamines as potent and selective serotonin reuptake inhibitors (SSRIs). Noticeably, the presence of the second bromine (the bromine passenger ) on the substrate was not significantly deleterious to the reaction although a small amount of the 7-bromoindole might be sacrificed at the end of the reaction to consume the active palladium catalyst. The approach to 7-bromoindole could provide a general method to access 7-bromoindoles (a rare class of indole derivatives), which then could be further manipulated for the synthesis of more complex 7-substituted indoles. 

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