4-PhPr-PEA

Last updated

4-PhPr-PEA
4-Phenylpropylphenethylamine.svg
Clinical data
Other names4-(3-Phenylpropyl)phenethylamine; 4-PhPr-PEA; 4-PPPEA
Drug class Serotonin receptor modulator; Serotonin 5-HT2A and 5-HT2C receptor modulator
ATC code
  • None
Identifiers
  • 2-[4-(3-phenylpropyl)phenyl]ethanamine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C17H21N
Molar mass 239.362 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)CCCC2=CC=C(C=C2)CCN
  • InChI=1S/C17H21N/c18-14-13-17-11-9-16(10-12-17)8-4-7-15-5-2-1-3-6-15/h1-3,5-6,9-12H,4,7-8,13-14,18H2
  • Key:YMVIIWYVJUTVGJ-UHFFFAOYSA-N

4-Phenylpropylphenethylamine (4-PhPr-PEA or 4-PPPEA), is a serotonin receptor modulator of the phenethylamine family related to phenethylamine (PEA). [1] [2] [3] [4] It is the 4-(3-phenylpropyl) derivative of phenethylamine. [1] [2] The drug shows relatively high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 60 nM and 525 nM, respectively). [1] [2] [4] Its affinity for the serotonin 5-HT2A receptor was 280-fold higher than that of phenethylamine (which was Ki = 16,800 nM). [1] 4-PhPr-PEA was not specifically assessed itself, but analogues were tested, and based on the results with them, the drug is assumed to act as an antagonist or low-efficacy partial agonist of the serotonin 5-HT2A receptor. [1] [2] [3] [4] 4-PhPr-PEA is notable as it indicates that methoxy groups on the phenyl ring are not required for high affinity binding to serotonin receptors, though they do appear to be required for efficacious agonism. [1] [3] [4] The drug was first described in the scientific literature by Richard Glennon and colleagues in 2000. [1] [2]

Contents

See also

References

  1. 1 2 3 4 5 6 7 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 283–284, 415–416, 480–481. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  2. 1 2 3 4 5 Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, et al. (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". Journal of Medicinal Chemistry. 43 (16): 3074–3084. doi:10.1021/jm9906062. PMID   10956215.
  3. 1 2 3 Trachsel D, Nichols DE, Kidd S, Hadorn M, Baumberger F (May 2009). "4-aryl-substituted 2,5-dimethoxyphenethylamines: synthesis and serotonin 5-HT(2A) receptor affinities". Chemistry & Biodiversity. 6 (5): 692–704. doi:10.1002/cbdv.200800235. PMID   19479848. Until recently, it was thought that the 2',5'-(MeO)2 pattern was required for high affinity of phenethylamines at the serotonin 5-HT2A receptor (reviewed in [11]). Although this pharmacophore may be necessary for agonist action, assumed to be the primary pharmacology of hallucinogenic phenethylamines [36] [37], Glennon and coworkers [11] [32] have shown that this substitution pattern is not required for high-affinity antagonists such as 13–15.
  4. 1 2 3 4 Runyon SP, Mosier PD, Roth BL, Glennon RA, Westkaemper RB (November 2008). "Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation". Journal of Medicinal Chemistry. 51 (21): 6808–6828. doi:10.1021/jm800771x. PMC   3088499 . PMID   18847250. In the DOX series, compounds with small substituents at the 4-position are agonists and those with bulky substituents such as phenylpropyl are antagonists.13,15 In the latter case, the 2,5-dimethoxy groups of 1-(2,5-dimethoxy-4- (3-phenylpropyl)phenyl)-2-aminopropane (2c), functional groups characteristically required for agonist activity, are no longer required for binding and, in fact, the desmethoxy parent 3c has comparable affinity to the 2,5-dimethoxy-substituted derivative.13,15
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.