2C-Ph, also known as 2C-BI-1 or as 2,5-dimethoxy-4-phenylphenethylamine, is a serotonin receptor modulator of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace am ...

and 2C families that was developed by

Daniel Trachsel Daniel Trachsel is a Swiss chemist who studies psychedelics and entactogens. He has developed and published on a large number of novel psychedelic and entactogen compounds, including their psychoactive effects. This has been in a manner similar ...

and

David E. Nichols David Earl Nichols (born December 23, 1944, Covington, Kentucky) is an American pharmacologist and medicinal chemist. Previously the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has w ...

and colleagues. The drug's

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Part ...

(K_i) for the rat serotonin 5-HT_2A receptor was 778nM. It was said to be an antagonist of this receptor. In a subsequent study, 2C-Ph was a weak

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonist ...

of the human serotonin 5-HT_2A receptor (K_i = 630nM, = 1,596nM, = 23%). 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. In addition, it interacted with other

monoamine receptor A monoamine receptor is a receptor for the monoamine neurotransmitters and/or trace amines, endogenous small-molecule signaling molecules with a monoamine structure. The monoamine receptors are almost all G protein-coupled receptors, with the ...

s, with the

monoamine transporter Monoamine transporters (MATs) are protein structures that function as integral plasma-membrane transporters to regulate concentrations of extracellular monoamine neurotransmitters. Three major classes of MATs (SERT, DAT, NET) are responsible for ...

s, and was a

potent Potent may refer to: * for the heraldic fur *Warren Potent for the Australian Olympic medalist in shooting See also: *Potency (disambiguation) Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biologica ...

and high-efficacy partial agonist of the human

trace amine-associated receptor 1 Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene. TAAR1 is an intracellular amine-activated and G protein-coupled receptor (GPCR) that is primarily ex ...

(TAAR1) ( = 580nM, = 82%). Besides 2C-Ph itself, a variety of

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

s of 2C-Ph with

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and '' functional group'', as well as '' ...

s on the 4-position phenyl ring have been synthesized and studied by Trachsel and colleagues. These drugs, inclusive of 2C-Ph, have been denoted 2C-BI-1 to 2C-BI-12. 2C-BI-4 (the 2′-trifluoromethyl derivative),

2C-BI-8 2C-BI-8, also known as 2,5-dimethoxy-4-(4-methoxyphenyl)phenethylamine or as 4′-methoxy-2C-Ph, is a serotonin receptor agonist of the substituted phenethylamine, phenethylamine and 2C (psychedelics), 2C families. It is the chemical derivative, ...

(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 ( = 37–2,408nM, = 38–44%). The effects of 2C-Ph and its derivatives in humans are unknown. However, 2C-BI-8 and 2C-BI-12, the most potent agonists, in particular might have the potential for

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science ...

effects. 2C-Ph was first described in the

scientific literature : ''For a broader class of literature, see Academic publishing.'' Scientific literature comprises scholarly publications that report original empirical and theoretical work in the natural and social sciences. Within an academic field, sci ...

, by Trachsel and Nichols and colleagues, in 2009.

References

External links

2C-Ph (2C-BI-1) - Isomer Design
2,5-Dimethoxyphenethylamines 2C (psychedelics) 5-HT2A agonists Biphenyls Serotonin receptor modulators TAAR1 agonists {{Psychoactive-stub