2C-Ph

2C-Ph
Clinical data
Other names	2C-BI-1; 2,5-Dimethoxy-4-phenylphenethylamine; 4-Phenyl-2,5-dimethoxyphenethylamine
Drug class	Serotonin receptor modulator
Identifiers
	IUPAC name 2-(2,5-dimethoxy[1,1′-biphenyl]-4-yl)ethan-1-amine;
PubChem CID	57474287;
Chemical and physical data
Formula	C16H19NO2
Molar mass	257.333 g·mol?1
3D model (JSmol)	Interactive image;
	SMILES NCCc1cc(OC)c(cc1OC)c1ccccc1;
	InChI 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;

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2C-Ph, 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]

The drug's affinity (K_i) for the rat serotonin 5-HT_2A receptor was 778 nM.^[1]^[2] It was said to be an antagonist of this receptor.^[1]^[2] In a subsequent study, 2C-Ph was a weak partial agonist of the human serotonin 5-HT_2A receptor (K_i = 630 nM, EC₅₀Tooltip half-maximal effective concentration = 1,596 nM, E_maxTooltip maximal efficacy = 23%).^[3] The drug also shows affinity for the serotonin 5-HT_1A, 5-HT_2B, and 5-HT_2C receptors, but did not activate the serotonin 5-HT_2B 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, E_max = 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-HT_2A receptor with higher efficacy than 2C-Ph (EC₅₀ = 37–2,408 nM, E_max = 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]

References

^ ^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.
^ ^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.
^ ^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.

External links

2C-Ph (2C-BI-1) - Isomer Design

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[TrachselLehmanEnzensperger2013-1] ^ ^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.

[TrachselNicholsKidd2009-2] ^ ^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.

[LuethiWidmerTrachsel2019-3] ^ ^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.

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See also

References

External links