Biscaline, also known as 3,5-dimethoxy-4-phenylphenethylamine, is a

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 se ...

modulator Signal modulation is the process of varying one or more properties of a periodic waveform in electronics and telecommunication for the purpose of transmitting information. The process encodes information in form of the modulation or message ...

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 ami ...

family. It is the analogue of

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

(3,4,5-dimethoxyphenethylamine) in which the

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

group A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic iden ...

at the 4 position has been replaced with a phenyl ring. The drug shows

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 Pa ...

for the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_1A receptor (K_i = 4,021nM). Conversely, it did not bind to the serotonin 5-HT_2A, 5-HT_2B, or 5-HT_2C receptors at the assessed concentrations (K_i = >13,400nM, >10,000nM, and >14,590nM, respectively). It is said to have lacked activational effects on the serotonin 5-HT_2A and 5-HT_2B receptors at the assessed concentrations. Biscaline also bound to the α_2A-adrenergic receptor (K_i = 797nM), but not to the α_1A-adrenergic receptor, the

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

D₂ receptor, or the

monoamine transporter Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...

s (, , or ) at the assessed concentrations (K_i = >7,510–10,550nM). It was a very weak monoamine reuptake inhibitor, with values of 457,000nM for

, 160,000nM for

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

, and 573,000nM for

. Besides the

s and transporters, biscaline showed affinity for the rat

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 a primarily intracellular amine-activated and G protein-coupled receptor (GPCR) that is p ...

(TAAR1) (K_i = 586nM), but not for the mouse TAAR1 (K_i = >4,270nM) and did not activate the human TAAR1 ( = >30,000nM). Biscaline's interaction with the α_2A-adrenergic receptor may be the only significant human pharmacological interaction detected with the compound so far. Due to its lack of activation of the serotonin 5-HT_2A receptor, biscaline would not be expected to produce psychedelic effects. A variety of 2C analogues and derivatives of biscaline have been synthesized and studied, such as 2C-Ph (2C-BI-1).

References

External links

Biscaline - Isomer Design
Adrenergic receptor modulators Biphenyls Methoxy compounds Scalines Serotonin receptor modulators TAAR1 modulators {{Psychoactive-stub

See also

References

External links