Biscaline

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]

Other names4-Phenyl-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-phenylphenethylamine

Drug classMonoamine receptor modulator

FormulaC₁₆H₁₉NO₂

Molar mass257.333 g·mol⁻¹

Quick facts Clinical data, Other names ...

Biscaline

Clinical data
Other names	4-Phenyl-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-phenylphenethylamine
Drug class	Monoamine receptor modulator
Identifiers
IUPAC name 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)	Interactive image
SMILES NCCc1cc(OC)c(c(c1)OC)c1ccccc1
InChI 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

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The drug shows affinity for the serotonin 5-HT_1A receptor (K_i = 4,021 nM).^[1] 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 = >13,400 nM, >10,000 nM, and >14,590 nM, respectively).^[1] It is said to have lacked activational effects on the serotonin 5-HT_2A and 5-HT_2B receptors at the assessed concentrations.^[1] Biscaline also bound to the α_2A-adrenergic receptor (K_i = 797 nM), but not to the α_1A-adrenergic receptor, the dopamine D₂ receptor, or the monoamine transporters (SERTTooltip serotonin transporter, NETTooltip norepinephrine transporter, or DATTooltip dopamine transporter) at the assessed concentrations (K_i = >7,510–10,550 nM).^[1] It was a very weak monoamine reuptake inhibitor, with IC₅₀Tooltip 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) (K_i = 586 nM), but not for the mouse TAAR1 (K_i = >4,270 nM) and did not activate the human TAAR1 (EC₅₀Tooltip half-maximal effective concentration = >30,000 nM).^[1] Biscaline's interaction with the α_2A-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-HT_2A 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]