PPPA (drug)

PPPA (drug)

Systematic (IUPAC) name
3-Phenoxy-3-phenyl-1-propanamine
Identifiers
ATC code	None
ChemSpider	14379241
Chemical data
Formula	C15H17NO
Molecular mass	227.302 g/mol
SMILES c1ccc(cc1)C(CCN)Oc2ccccc2
InChI InChI=1S/C15H17NO/c16-12-11-15(13-7-3-1-4-8-13)17-14-9-5-2-6-10-14/h1-10,15H,11-12,16H2 Key:XYWLZHPZECQHMB-UHFFFAOYSA-N

PPPA, or 3-phenoxy-3-phenylpropan-1-amine, is a drug which is described as an antidepressant. It was derived by Eli Lilly from the antihistamine diphenhydramine, a 2-diphenylmethoxyethanamine derivative with additional properties as a selective serotonin reuptake inhibitor (SSRI), and has been the basis for the subsequent discovery of a number of other antidepressant drugs.

List of PPPA derivatives

• Atomoxetine ((3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine) - NRI
• Fluoxetine (N-methyl-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) - SSRI
• N-Methyl-PPPA (N-methyl-3-phenoxy-3-phenylpropan-1-amine) - SNRI
• Nisoxetine (N-methyl-3-(2-methoxyphenoxy)-3-phenylpropan-1-amine) - NRI
• Norfluoxetine (3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) - SSRI
• Seproxetine ((S)-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) - SSRI

Structurally related drugs include dapoxetine, duloxetine, edivoxetine, femoxetine, paroxetine, reboxetine, and viloxazine, all of which act, similarly, as monoamine reuptake inhibitors, and most of which are, again similarly, antidepressants.

Zimelidine is an antidepressant and SSRI which was derived from the antihistamine pheniramine, which, similarly to its analogues brompheniramine and chlorpheniramine, possesses SNRI properties. Fluvoxamine, another antidepressant and SSRI, was developed from the antihistamine tripelennamine, which possesses SNDRI actions.

See also

• Development and discovery of SSRI drugs
• Lometraline