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2C-Ph

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2C-Ph
Clinical data
Other names2C-Phenyl; 2C-BI-1; 2,5-Dimethoxy-4-phenylphenethylamine; 4-Phenyl-2,5-dimethoxyphenethylamine
Drug classSerotonin receptor modulator
Identifiers
  • 2-(2,5-dimethoxy[1,1′-biphenyl]-4-yl)ethan-1-amine
PubChem CID
Chemical and physical data
FormulaC16H19NO2
Molar mass257.333 g·mol−1
3D model (JSmol)
  • NCCc1cc(OC)c(cc1OC)c1ccccc1
  • InChI=1S/C16H19NO2/c1-18-15-11-14(12-6-4-3-5-7-12)16(19-2)10-13(15)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3
  • Key:RMMCNNHGPNUXOX-UHFFFAOYSA-N

2C-Ph, or 2C-Phenyl, also known as 2C-BI-1 or as 2,5-dimethoxy-4-phenylphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families that was developed by Daniel Trachsel and David E. Nichols and colleagues.[1][2][3][4]

The drug's affinity (Ki) for the rat serotonin 5-HT2A receptor was 778 nM.[1][2] It was said to be an antagonist of this receptor.[1][2][4] In a subsequent study, 2C-Ph was a weak partial agonist of the human serotonin 5-HT2A receptor (Ki = 630 nM, EC50Tooltip half-maximal effective concentration = 1,596 nM, EmaxTooltip maximal efficacy = 23%).[3] The drug also shows affinity for the serotonin 5-HT1A, 5-HT2B, and 5-HT2C receptors, but did not activate the serotonin 5-HT2B receptor.[3] In addition, it interacted with other monoamine receptors, with the monoamine transporters, and was a potent and high-efficacy partial agonist of the human trace amine-associated receptor 1 (TAAR1) (EC50 = 580 nM, Emax = 82%).[3]

Besides 2C-Ph itself, a variety of derivatives of 2C-Ph with substituents on the 4-position phenyl ring have been synthesized and studied by Trachsel and colleagues.[1][2][3] These drugs, inclusive of 2C-Ph, have been denoted 2C-BI-1 to 2C-BI-12.[1][2][3] 2C-BI-4 (the 2′-trifluoromethyl derivative), 2C-BI-8 (the 4′-methoxy derivative), and 2C-BI-12 (the 3′,4′-dimethoxy derivative) are agonists of the human serotonin 5-HT2A receptor with higher efficacy than 2C-Ph (EC50 = 37–2,408 nM, Emax = 38–44%).[3] The effects of 2C-Ph and its derivatives in humans are unknown.[1][3] However, 2C-BI-8 and 2C-BI-12, the most potent agonists, in particular might have the potential for psychedelic effects.[3]

2C-Ph was first described in the scientific literature, by Trachsel and Nichols and colleagues, in 2009.[1][2]

See also

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References

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  1. ^ a b c d e f g Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German). Solothurn: Nachtschatten-Verlag. p. 806. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 29 January 2025.
  2. ^ a b c d e f 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.
  3. ^ a b c d e f g h i Luethi D, Widmer R, Trachsel D, Hoener MC, Liechti ME (July 2019). "Monoamine receptor interaction profiles of 4-aryl-substituted 2,5-dimethoxyphenethylamines (2C-BI derivatives)". European Journal of Pharmacology. 855: 103–111. doi:10.1016/j.ejphar.2019.05.014. PMID 31063768.
  4. ^ a b Yempala T, Brea J, Loza MI, Matthies DJ, Zapata-Torres G, Cassels BK (February 2020). "Dibenzofuranylethylamines as 5-HT2A/2C Receptor Agonists". ACS Omega. 5 (5): 2260–2266. doi:10.1021/acsomega.9b03430. PMC 7016908. PMID 32064387. Regarding the weakly binding compound 3, which is practically devoid of (partial) agonist activity at both receptor subtypes, it may be seen as a cyclized version of the 5-HT2A antagonist 2-(2,5-dimethoxy-4-phenylphenyl)ethanamine (2C-phenyl, compound 7 in Trachsel et al., 2009).23 However, the orientation of the oxygen lone pairs on the dibenzofuran ring is "wrong" for hydrogen bonding,6,7 as corroborated by the higher affinities of 2C-phenyl and the "Fly" and "Dragonfly" compounds with "correct" orientations and pKi values of 6.11 and greater than 8, respectively, at the 5-HT2A receptor (the 5-HT2C affinities of 2C-phenyl and the "Fly/Dragonfly" compounds are not available, nor are their functional activities at this receptor). Nevertheless, it should be noted, however, that while 2C-H-Fly elicited a positive drug discrimination response in LSD-trained rats, suggesting that it is a 5-HT2A agonist, and 3 is a very weak partial agonist, 2C-phenyl is an antagonist at this receptor (Figure 6). [...] Figure 6. Comparison of the structures of compound 3, 2C-phenyl, and "Fly" (with dihydrofuran rings) and "Dragonfly" compounds (with furan rings).
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