making yohimbine more water soluble?

[Sigmund Roid]

A question for the chemists

Yohimbine contains an =NH group and an -OH group. Thus, can I increase the water solubility from 1% to a higher percentage by adding a little NaOH to the solution?

 

[gainerxxl]

Isn´t yohimbine HCL water soluble? Most HCL´s are.
If I´m wrong, Yohimbine will be soluble in a non (or less) polar solvent, such as acetone, some Alcohols, and alkanes, so raising the ph won´t do much regarding solubility.

 

[Sigmund Roid]

Yohimbine HCl is only soluble in a concentration of 10 mg / ml (1%). I would like to increase the solubility to say 20%.

As an example, glipizide, a compound with an NH group, is insoluble in water, but very soluble in 0.1 N NaOH. I wonder if the same thing applies to yoh.

I have tried solving yohimbine in acetone, but the result is very poor also.