PPPA (drug)

PPPA, or 3-phenoxy-3-phenylpropan-1-amine, is a drug which is described as an antidepressant.[1] 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.[2][3][4]

PPPA
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 3-Phenoxy-3-phenyl-1-propanamine
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC15H17NO
Molar mass227.307 g·mol−1
3D model (JSmol)
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

List of PPPA derivatives

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.[1][3]

Zimelidine is an antidepressant and SSRI which was derived from the antihistamine pheniramine, which, similarly to its analogues brompheniramine and chlorpheniramine, possesses SNRI properties.[4] Fluvoxamine, another antidepressant and SSRI, was developed from the antihistamine tripelennamine, which possesses SNDRI actions.[6]

See also

References
  1. Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 414–. ISBN 978-0-7817-6879-5.
  2. Francisco Lopez-Munoz; Cecilio Alamo (9 September 2011). Neurobiology of Depression. CRC Press. pp. 132–. ISBN 978-1-4398-3850-1.
  3. Janos Fischer; C. Robin Ganellin (24 August 2010). Analogue-based Drug Discovery II. John Wiley & Sons. pp. 35, 282, 284. ISBN 978-3-527-63212-1.
  4. Walter Sneader (31 October 2005). Drug Discovery: A History. John Wiley & Sons. pp. 416–417. ISBN 978-0-470-01552-0.
  5. David G. Watson (9 February 2011). Pharmaceutical Chemistry. Elsevier Health Sciences. pp. 1061–. ISBN 978-0-7020-4850-0.
  6. David Healy (1 June 2004). Let Them Eat Prozac: The Unhealthy Relationship Between the Pharmaceutical Industry and Depression. NYU Press. pp. 295–. ISBN 978-0-8147-7300-0.

Further reading
  • Wong DT, Bymaster FP, Engleman EA (1995). "Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication". Life Sci. 57 (5): 411–41. doi:10.1016/0024-3205(95)00209-o. PMID 7623609.
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