Chemistry:4-PhPr-PEA

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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]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 283–284, 415–416, 480–481. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". Journal of Medicinal Chemistry 43 (16): 3074–3084. August 2000. doi:10.1021/jm9906062. PMID 10956215. 
  3. ↑ 3.0 3.1 3.2 "4-aryl-substituted 2,5-dimethoxyphenethylamines: synthesis and serotonin 5-HT(2A) receptor affinities". Chemistry & Biodiversity 6 (5): 692–704. May 2009. 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. ↑ 4.0 4.1 4.2 4.3 "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. November 2008. doi:10.1021/jm800771x. 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". 



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