3-PPP

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3-PPP
3-PPP.svg
Clinical data
Synonyms Preclamol
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEBI
ChEMBL
Chemical and physical data
Formula C14H21NO
Molar mass 219.328 g/mol
3D model (JSmol)

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)[1] and D2 receptor partial agonist which is used in scientific research.[2][3] It shows stereoselectivity in its pharmacodynamics.[2] (+)-3-PPP is the enantiomer that acts as an agonist of the sigma receptors;[3] it is also an agonist of both D2 presynaptic and postsynaptic receptors.[2] Conversely, (–)-3-PPP, also known as preclamol (INN), acts as an agonist of presynaptic D2 receptors but as an antagonist of postsynaptic D2 receptors, and has antipsychotic effects.[2][4] 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.[5]

See also[edit]

References[edit]

  1. ^ Hellewell SB, Bowen WD (1990). "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". Brain Res. 527 (2): 244–53. PMID 2174717. 
  2. ^ a b c d Hjorth S, Carlsson A, Clark D, Svensson K, Wikström H, Sanchez D, Lindberg P, Hacksell U, Arvidsson LE, Johansson A (1983). "Central dopamine receptor agonist and antagonist actions of the enantiomers of 3-PPP". Psychopharmacology. 81 (2): 89–99. PMID 6415751. 
  3. ^ a b Hellewell SB, Bruce A, Feinstein G, Orringer J, Williams W, Bowen WD (1994). "Rat liver and kidney contain high densities of sigma 1 and sigma 2 receptors: characterization by ligand binding and photoaffinity labeling". Eur. J. Pharmacol. 268 (1): 9–18. PMID 7925616. 
  4. ^ Jeffrey S. Albert (6 June 2012). Targets and Emerging Therapies for Schizophrenia. John Wiley & Sons. pp. 64–. ISBN 978-1-118-30940-7. 
  5. ^ Annual Reports in Medicinal Chemistry. Academic Press. 5 October 1993. pp. 14–. ISBN 978-0-08-058372-3.