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'''PPPA''', or '''3-phenoxy-3-phenylpropan-1-amine''', is a [[drug]] which is described as an [[antidepressant]].<ref name="LemkeWilliams2008">{{cite book|author1=Thomas L. Lemke|author2=David A. Williams|title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA414|year=2008|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-6879-5|pages=414–}}</ref> 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.<ref name="Lopez-MunozAlamo2011">{{cite book|author1=Francisco Lopez-Munoz|author2=Cecilio Alamo|title=Neurobiology of Depression|url=https://books.google.com/books?id=lmXRBQAAQBAJ&pg=PA132|date=9 September 2011|publisher=CRC Press|isbn=978-1-4398-3850-1|pages=132–}}</ref><ref name="FischerGanellin2010">{{cite book|author1=Janos Fischer|author2=C. Robin Ganellin|title=Analogue-based Drug Discovery II|url=https://books.google.com/books?id=h2Kd8ci4Ln8C&pg=PA282|date=24 August 2010|publisher=John Wiley & Sons|isbn=978-3-527-63212-1|pages=35, 282, 284}}</ref><ref name="Sneader2005">{{cite book|author=Walter Sneader|title=Drug Discovery: A History|url=https://books.google.com/books?id=jglFsz5EJR8C&pg=PA416|date=31 October 2005|publisher=John Wiley & Sons|isbn=978-0-470-01552-0|pages=416–417}}</ref>
'''PPPA''', or '''3-phenoxy-3-phenylpropan-1-amine''', is a [[drug]] which is described as an [[antidepressant]].<ref name="LemkeWilliams2008">{{cite book| vauthors = Glennon RA, Dukat-Glennon M | chapter = Serotonin Receptors and Drugs Affecting Serotonergic Neurotransmission | veditors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry| chapter-url= https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA414|year=2008|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-6879-5|pages=414–}}</ref> 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.<ref name="Lopez-MunozAlamo2011">{{cite book | vauthors = López-Muñoz F, Álamo C | chapter = Contribution of Pharmacology to Development of Monoaminergic Hypotheses of Depression | veditors = López-Muñoz F, Álamo C |title=Neurobiology of Depression|chapter-url=https://books.google.com/books?id=lmXRBQAAQBAJ&pg=PA132|date=9 September 2011|publisher=CRC Press|isbn=978-1-4398-3850-1|pages=132–}}</ref><ref name="FischerGanellin2010">{{cite book| vauthors = Childers Jr WE, Rotella DP | chapter = Selective Serotonin Reuptake Inhibitors for the Treatment of Depression| veditors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery II| chapter-url = https://books.google.com/books?id=h2Kd8ci4Ln8C&pg=PA282|date=24 August 2010|publisher=John Wiley & Sons|isbn=978-3-527-63212-1|pages=35, 282, 284}}</ref><ref name="Sneader2005">{{cite book| vauthors = Sneader W | chapter = Drugs Originating from the Screening of Organic Chemicals |title=Drug Discovery: A History| chapter-url = https://books.google.com/books?id=jglFsz5EJR8C&pg=PA416|date=31 October 2005|publisher=John Wiley & Sons|isbn=978-0-470-01552-0|pages=416–417}}</ref>


==List of PPPA derivatives==
==List of PPPA derivatives==
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* [[Nisoxetine]] (''N''-methyl-3-(2-methoxyphenoxy)-3-phenylpropan-1-amine) — NRI<ref name="LemkeWilliams2008" />
* [[Nisoxetine]] (''N''-methyl-3-(2-methoxyphenoxy)-3-phenylpropan-1-amine) — NRI<ref name="LemkeWilliams2008" />
* [[Norfluoxetine]] (3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI<ref name="FischerGanellin2010" />
* [[Norfluoxetine]] (3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI<ref name="FischerGanellin2010" />
* [[Seproxetine]] ((''S'')-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI<ref name="Watson2011">{{cite book|author=David G. Watson|title=Pharmaceutical Chemistry|url=https://books.google.com/books?id=-lQM4xHjWeUC&pg=PT1061|date=9 February 2011|publisher=Elsevier Health Sciences|isbn=978-0-7020-4850-0|pages=1061–}}</ref>
* [[Seproxetine]] ((''S'')-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI<ref name="Watson2011">{{cite book| vauthors = Brandt SD | chapter = CNS stimulants and CNS-active drugs affecting the serotonergic system| veditors = Watson DG |title=Pharmaceutical Chemistry|chapter-url=https://books.google.com/books?id=-lQM4xHjWeUC&pg=PT1061|date=9 February 2011|publisher=Elsevier Health Sciences|isbn=978-0-7020-4850-0|pages=1061–}}</ref>


Structurally related drugs include [[dapoxetine]], [[duloxetine]], [[edivoxetine]], [[femoxetine]], [[paroxetine]], [[reboxetine]], and [[viloxazine]], all of which act, similarly, as [[monoamine reuptake inhibitor]]s, and most of which are, again similarly, antidepressants.<ref name="LemkeWilliams2008" /><ref name="FischerGanellin2010" />
Structurally related drugs include [[dapoxetine]], [[duloxetine]], [[edivoxetine]], [[femoxetine]], [[paroxetine]], [[reboxetine]], and [[viloxazine]], all of which act, similarly, as [[monoamine reuptake inhibitor]]s, and most of which are, again similarly, antidepressants.<ref name="LemkeWilliams2008" /><ref name="FischerGanellin2010" />


[[Zimelidine]] is an antidepressant and SSRI which was derived from the antihistamine [[pheniramine]], which, similarly to its analogues [[brompheniramine]] and [[chlorpheniramine]], possesses SNRI properties.<ref name="Sneader2005" /> [[Fluvoxamine]], another antidepressant and SSRI, was developed from the antihistamine [[tripelennamine]], which possesses [[Serotonin–norepinephrine–dopamine reuptake inhibitor|SNDRI]] actions.<ref name="Healy2004">{{cite book|author=David Healy|title=Let Them Eat Prozac: The Unhealthy Relationship Between the Pharmaceutical Industry and Depression|url=https://books.google.com/books?id=5w64WC_-jbMC&pg=PA295|date=1 June 2004|publisher=NYU Press|isbn=978-0-8147-7300-0|pages=295–}}</ref>
[[Zimelidine]] is an antidepressant and SSRI which was derived from the antihistamine [[pheniramine]], which, similarly to its analogues [[brompheniramine]] and [[chlorpheniramine]], possesses SNRI properties.<ref name="Sneader2005" /> [[Fluvoxamine]], another antidepressant and SSRI, was developed from the antihistamine [[tripelennamine]], which possesses [[Serotonin–norepinephrine–dopamine reuptake inhibitor|SNDRI]] actions.<ref name="Healy2004">{{cite book| vauthors = Healy D |title=Let Them Eat Prozac: The Unhealthy Relationship Between the Pharmaceutical Industry and Depression |url=https://books.google.com/books?id=5w64WC_-jbMC&pg=PA295|date=1 June 2004|publisher=NYU Press|isbn=978-0-8147-7300-0|pages=295–}}</ref>


==See also==
== See also ==
* [[Development and discovery of SSRI drugs]]
* [[Development and discovery of SSRI drugs]]
* [[Serotonin–norepinephrine_reuptake_inhibitor#Aryloxypropanamine_scaffold|Aryloxypropanamine scaffold]]
* [[Serotonin–norepinephrine_reuptake_inhibitor#Aryloxypropanamine_scaffold|Aryloxypropanamine scaffold]]
* [[Lometraline]]
* [[Lometraline]]


==References==
== References ==
{{Reflist|2}}
{{Reflist|2}}


==Further reading==
== Further reading ==
{{refbegin}}
* {{cite journal | vauthors = Wong DT, Bymaster FP, Engleman EA | title = Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication | journal = Life Sci. | volume = 57 | issue = 5 | pages = 411–41 | year = 1995 | pmid = 7623609 | doi = 10.1016/0024-3205(95)00209-o}}
* {{cite journal | vauthors = Wong DT, Bymaster FP, Engleman EA | title = Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication | journal = Life Sciences | volume = 57 | issue = 5 | pages = 411–441 | year = 1995 | pmid = 7623609 | doi = 10.1016/0024-3205(95)00209-o }}
{{refend}}


{{Antidepressants}}
{{Antidepressants}}

Latest revision as of 09:49, 28 December 2023

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

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]

List of PPPA derivatives

[edit]

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

[edit]

References

[edit]
  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

[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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