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]
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| Formula | C15H17NO |
| Molar mass | 227.307 g·mol−1 |
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List of PPPA derivatives
edit- 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
editReferences
edit- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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
edit- 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.
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