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 diphenylmethane 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
  • 3-Phenoxy-3-phenyl-1-propanamine
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC15H17NO
Molar mass227.307 g·mol−1
3D model (JSmol)
  • c1ccc(cc1)C(CCN)Oc2ccccc2
  • 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

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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

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References

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  1. ^ a b c d Glennon RA, Dukat-Glennon M (2008). "Serotonin Receptors and Drugs Affecting Serotonergic Neurotransmission". In Lemke TL, Williams DA (eds.). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 414–. ISBN 978-0-7817-6879-5.
  2. ^ a b c López-Muñoz F, Álamo C (9 September 2011). "Contribution of Pharmacology to Development of Monoaminergic Hypotheses of Depression". In López-Muñoz F, Álamo C (eds.). Neurobiology of Depression. CRC Press. pp. 132–. ISBN 978-1-4398-3850-1.
  3. ^ a b c Childers Jr WE, Rotella DP (24 August 2010). "Selective Serotonin Reuptake Inhibitors for the Treatment of Depression". In Fischer J, Ganellin CR (eds.). Analogue-based Drug Discovery II. John Wiley & Sons. pp. 35, 282, 284. ISBN 978-3-527-63212-1.
  4. ^ a b c Sneader W (31 October 2005). "Drugs Originating from the Screening of Organic Chemicals". Drug Discovery: A History. John Wiley & Sons. pp. 416–417. ISBN 978-0-470-01552-0.
  5. ^ Brandt SD (9 February 2011). "CNS stimulants and CNS-active drugs affecting the serotonergic system". In Watson DG (ed.). Pharmaceutical Chemistry. Elsevier Health Sciences. pp. 1061–. ISBN 978-0-7020-4850-0.
  6. ^ Healy D (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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  • 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 Sciences. 57 (5): 411–441. doi:10.1016/0024-3205(95)00209-o. PMID 7623609.