Biscaline

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Biscaline
Biscaline.svg
Clinical data
Other names4-Phenyl-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-phenylphenethylamine
Drug class Monoamine receptor modulator
Identifiers
  • 2-(2,6-dimethoxy[1,1′-biphenyl]-4-yl)ethan-1-amine
Chemical and physical data
Formula C16H19NO2
Molar mass 257.333 g·mol−1
3D model (JSmol)
  • NCCc1cc(OC)c(c(c1)OC)c1ccccc1
  • InChI=1S/C16H19NO2/c1-18-14-10-12(8-9-17)11-15(19-2)16(14)13-6-4-3-5-7-13/h3-7,10-11H,8-9,17H2,1-2H3
  • Key:ZDAUKFAGIRVDHK-UHFFFAOYSA-N

Biscaline, also known as 3,5-dimethoxy-4-phenylphenethylamine, is a monoamine receptor modulator of the phenethylamine family. [1] It is the analogue of mescaline (3,4,5-dimethoxyphenethylamine) in which the methoxy group at the 4 position has been replaced with a phenyl ring. [1]

Contents

The drug shows affinity for the serotonin 5-HT1A receptor (Ki = 4,021 nM). [1] Conversely, it did not bind to the serotonin 5-HT2A, 5-HT2B, or 5-HT2C receptors at the assessed concentrations (Ki = >13,400 nM, >10,000 nM, and >14,590 nM, respectively). [1] It is said to have lacked activational effects on the serotonin 5-HT2A and 5-HT2B receptors at the assessed concentrations. [1] Biscaline also bound to the α2A-adrenergic receptor (Ki = 797 nM), but not to the α1A-adrenergic receptor, the dopamine D2 receptor, or the monoamine transporters (SERT Tooltip serotonin transporter, NET Tooltip norepinephrine transporter, or DAT Tooltip dopamine transporter) at the assessed concentrations (Ki = >7,510–10,550 nM). [1] It was a very weak monoamine reuptake inhibitor, with IC50 Tooltip half-maximal inhibitory concentration values of 457,000 nM for serotonin, 160,000 nM for norepinephrine, and 573,000 nM for dopamine. [1]

Besides the monoamine receptors and transporters, biscaline showed affinity for the rat trace amine-associated receptor 1 (TAAR1) (Ki = 586 nM), but not for the mouse TAAR1 (Ki = >4,270 nM) and did not activate the human TAAR1 (EC50 Tooltip half-maximal effective concentration = >30,000 nM). [1] Biscaline's interaction with the α2A-adrenergic receptor may be the only significant human pharmacological interaction detected with the compound so far. [1] Due to its lack of activation of the serotonin 5-HT2A receptor, biscaline would not be expected to produce psychedelic effects. [1]

A variety of 2C analogues and derivatives of biscaline have been synthesized and studied, such as 2C-Ph (2C-BI-1). [1]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 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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