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3-PPP

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3-PPP
Identifiers
  • (±)-3-(1-propylpiperidin-3-yl)phenol
CAS Number
PubChem CID
ChemSpider
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21NO
Molar mass219.328 g/mol g·mol−1
3D model (JSmol)
  • CCCN1CCCC(C1)C2=CC(=CC=C2)O
  • 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

3-(1-Propyl-3-piperidinyl)phenol (3-PPP) is a mixed sigma σ1 and σ2 receptor agonist (with similar affinity for both subtypes) and D2 receptor partial agonist which is used in scientific research.[1][2] It shows stereoselectivity in its pharmacodynamics.[1] (+)-3-PPP is the enantiomer that acts as an agonist of the sigma receptors;[2] it is also an agonist of both D2 presynaptic and postsynaptic receptors.[1] Conversely, (–)-3-PPP, also known as preclamol (INNTooltip International Nonproprietary Name), acts as an agonist of presynaptic D2 receptors but as an antagonist of postsynaptic D2 receptors, and has antipsychotic effects.[1][3]

See also

References

  1. ^ 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 (Berl.). 81 (2): 89–99. PMID 6415751.
  2. ^ 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.
  3. ^ Jeffrey S. Albert (6 June 2012). Targets and Emerging Therapies for Schizophrenia. John Wiley & Sons. pp. 64–. ISBN 978-1-118-30940-7.