Is fluoxetine hydrochloride an ionic or covalent bond?

Question

I tried to figure it out myself but it wasn't adding up, need it for tomorrow in class.

Answer 1

Fluoxetine (Prozac) is a molecular (covalent) compound. Fluoxetine hydrochloride is the salt of that molecular compound, making it an ionic bond. As pointed out by Stanton D., the hydrochloride salt results from the addition of HCl to the free base (fluoxetine). The H⁺ is donated to the amine resulting in a quarternary amine (NH₄⁺) with the associated Cl^- ion forming the ionic bond and resulting in an ionic bond.

Answer 2

Hi Emily C.,

To what part of the fluoxetine hydrochloride salt structure are you referring? Generally, you'd think of the H+ as H-bonded (actually donated) to the amine nitrogen, and the Cl- ion as along for the ride as an ionic bond. Between molecules, the solid is no doubt packed in with mostly aromatic ring stacking, that's hydrophobic attraction. The chlorides and the amine chains also no doubt form alternating stacks, also (long-range ionic order).

By the way, it's an antidepressant and a serotonin-uptake inhibitor, just saying!

-- Cheers, -- Mr. d.