3-PPP

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]

3-PPP
Clinical data
Other namesPreclamol
Identifiers
IUPAC name
  • (±)-3-(1-Propylpiperidin-3-yl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21NO
Molar mass219.328 g·mol−1
3D model (JSmol)
SMILES
  • CCCN1CCCC(C1)C2=CC(=CC=C2)O
InChI
  • InChI=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
  • Key:HTSNFXAICLXZMA-UHFFFAOYSA-N

See also

References
  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): 244–253. doi:10.1016/0006-8993(90)91143-5. PMID 2174717.
  2. 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. doi:10.1007/bf00428999. PMID 6415751.
  3. 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. doi:10.1016/0922-4106(94)90115-5. 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.
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