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4-PhPr-PEA

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Pharmaceutical compound
4-PhPr-PEA
Clinical data
Other names4-(3-Phenylpropyl)phenethylamine; 4-PhPr-PEA; 4-PPPEA
Drug classSerotonin receptor modulator;Serotonin5-HT2A and5-HT2C receptormodulator
ATC code
  • None
Identifiers
  • 2-[4-(3-phenylpropyl)phenyl]ethanamine
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC17H21N
Molar mass239.362 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 or4-PPPEA), is aserotonin receptor modulator of thephenethylamine family related tophenethylamine (PEA).[1][2][3][4] It is the 4-(3-phenylpropyl)derivative of phenethylamine.[1][2] The drug shows relatively highaffinity for theserotonin5-HT2A and5-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, butanalogues were tested, and based on the results with them, the drug is assumed to act as anantagonist or low-efficacypartial agonist of the serotonin 5-HT2A receptor.[1][2][3][4] 4-PhPr-PEA is notable as it indicates thatmethoxy groups on thephenyl ring are not required for high affinity binding toserotonin receptors, though they do appear to be required for efficaciousagonism.[1][3][4] The drug was first described in thescientific literature byRichard Glennon and colleagues in 2000.[1][2]

See also

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References

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  1. ^abcdefgTrachsel 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 fromthe original on 21 August 2025.
  2. ^abcdeDowd 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. ^abcTrachsel 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. ^abcdRunyon 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

External links

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