3-PPP

{{Short description|Chemical compound}}

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| IUPAC_name = (±)-3-(1-Propylpiperidin-3-yl)phenol

| image = 3-PPP.svg

| width = 200px

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 75240-91-4

| CAS_supplemental =
85966-89-8 ((+)-isomer)

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| PubChem = 55445

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| ChemSpiderID_Ref =

| ChemSpiderID = 50067

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ND3NDM2EHM

| KEGG =

| ChEBI = 125440

| ChEMBL = 276500

| synonyms = Preclamol

| C=14 | H=21 | N=1 | O=1

| SMILES = CCCN1CCCC(C1)C2=CC(=CC=C2)O

| StdInChI_Ref =

| StdInChI = 1S/C14H21NO/c1-2-8-15-9-4-6-13(11-15)12-5-3-7-14(16)10-12/h3,5,7,10,13,16H,2,4,6,8-9,11H2,1H3

| StdInChIKey_Ref =

| StdInChIKey = HTSNFXAICLXZMA-UHFFFAOYSA-N

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3-PPP (N-n-propyl-3-(3-hydroxyphenyl)piperidine) is a mixed sigma σ₁ and σ₂ receptor agonist (with similar affinity for both subtypes, though slightly higher affinity for the latter){{cite journal | vauthors = Hellewell SB, Bowen WD | title = A sigma-like binding site in rat pheochromocytoma (PC12) cells: decreased affinity for (+)-benzomorphans and lower molecular weight suggest a different sigma receptor form from that of guinea pig brain | journal = Brain Res. | volume = 527 | issue = 2 | pages = 244–253 | year = 1990 | pmid = 2174717 | doi = 10.1016/0006-8993(90)91143-5| s2cid = 24546226 }} and D₂ receptor partial agonist which is used in scientific research.{{cite journal | vauthors = Hjorth S, Carlsson A, Clark D, Svensson K, Wikström H, Sanchez D, Lindberg P, Hacksell U, Arvidsson LE, Johansson A | title = Central dopamine receptor agonist and antagonist actions of the enantiomers of 3-PPP | journal = Psychopharmacology | volume = 81 | issue = 2 | pages = 89–99 | year = 1983 | pmid = 6415751 | doi = 10.1007/bf00428999| s2cid = 1168359 }}{{cite journal | vauthors = Hellewell SB, Bruce A, Feinstein G, Orringer J, Williams W, Bowen WD | title = Rat liver and kidney contain high densities of sigma 1 and sigma 2 receptors: characterization by ligand binding and photoaffinity labeling | journal = Eur. J. Pharmacol. | volume = 268 | issue = 1 | pages = 9–18 | year = 1994 | pmid = 7925616 | doi = 10.1016/0922-4106(94)90115-5}} It shows stereoselectivity in its pharmacodynamics. (+)-3-PPP is the enantiomer that acts as an agonist of the sigma receptors; it is also an agonist of both D₂ presynaptic and postsynaptic receptors. Conversely, (−)-3-PPP, also known as preclamol ({{abbrlink|INN|International Nonproprietary Name}}), acts as an agonist of presynaptic D₂ receptors but as an antagonist of postsynaptic D₂ receptors, and has antipsychotic effects.{{cite book|author=Jeffrey S. Albert|title=Targets and Emerging Therapies for Schizophrenia|url=https://books.google.com/books?id=L1Xnqh2GOdAC&pg=PT64|date=6 June 2012|publisher=John Wiley & Sons|isbn=978-1-118-30940-7|pages=64–}} 3-PPP has also been reported to be a monoamine reuptake inhibitor and possibly to act at adrenergic receptors or some other non-sigma receptor.{{cite book|title=Annual Reports in Medicinal Chemistry|url=https://books.google.com/books?id=648kNU6aMMYC&pg=PR14|date=5 October 1993|publisher=Academic Press|isbn=978-0-08-058372-3|pages=14–}}