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PPPA (drug)

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PPPA (drug)
File:3-phenoxy-3-phenylpropan-1-amine.svg
Systematic (IUPAC) name
3-Phenoxy-3-phenyl-1-propanamine
Clinical data
Identifiers
None
ChemSpider 14379241
Chemical data
Formula C15H17NO
227.302 g/mol

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]

List of PPPA derivatives

  • Atomoxetine ((3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine) - NRI[1]
  • Fluoxetine (N-methyl-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) - SSRI[2]
  • N-Methyl-PPPA (N-methyl-3-phenoxy-3-phenylpropan-1-amine) - SNRI[2][4]
  • Nisoxetine (N-methyl-3-(2-methoxyphenoxy)-3-phenylpropan-1-amine) - NRI[1]
  • Norfluoxetine (3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) - SSRI[3]
  • Seproxetine ((S)-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) - SSRI[5]

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. ^ a b c d 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. ^ a b c Francisco Lopez-Munoz; Cecilio Alamo (9 September 2011). Neurobiology of Depression. CRC Press. pp. 132–. ISBN 978-1-4398-3850-1. 
  3. ^ a b c 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. ^ a b c 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 0-7020-4850-X. 
  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



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