Hydroxy-5-methoxytryptamine

Hydroxy"5-methoxytryptamine produces an increase in exploratory behavior in animals, but not significant from controls. No effect on serotonin norepinephrine brief decrease in 5-hydroxyindole acetic acid (5-HIAA). (Maickei 1978)... 

Hydroxy-7-methoxytryptamine produced erratic running, vocalization with increased alertness in lab animals. There was no effect on serotonin except for Increase in 5-HIAA. 

Scheme 19 Nucleophilic substitution reaction of 1-hydroxy- and 1-methoxytryptamines having a substituent on the indole nucleus...

The projected free radical cyclization proceeded as planned to give 172. Ozonolysis of the vinyl group, oxidation of the resulting aldehyde to an acid, and alkylation with diazomethane provided projected intermediate 162. Reduction of the lactone provided 173. Treatment of 173 with 6-methoxytryptamine and pivalic acid then provided a nearly equal mixture of lactams 174 (isoreserpine stereochemistry at Cg) and 175 (reserpine stereochemistry at C3). The correct C3 stereoisomer was moved forward to 176 (protection of the tertiary alcohol followed by reduction of the lactam). The silyl ethers were removed, the secondary ether was re-protected, and reaction with samarium iodide accomplished reduction of the a-hydroxy ester to provide 177. Removal of the TBS group and esterification of the alcohol completed the synthesis of reserpine. 

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