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

Biscaline, also known as3,5-dimethoxy-4-phenylphenethylamine, is amonoamine receptormodulator of thephenethylamine family.^[1] It is theanalogue ofmescaline (3,4,5-dimethoxyphenethylamine) in which themethoxygroup at the 4 position has been replaced with aphenyl ring.^[1]

The drug showsaffinity for theserotonin5-HT_1A receptor (K_i = 4,021 nM).^[1] Conversely, it did not bind to the serotonin5-HT_2A,5-HT_2B, or5-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 theα_2A-adrenergic receptor (K_i = 797 nM), but not to theα_1A-adrenergic receptor, thedopamineD₂ receptor, or themonoamine transporters (SERTTooltip serotonin transporter,NETTooltip norepinephrine transporter, orDATTooltip dopamine transporter) at the assessed concentrations (K_i = >7,510–10,550 nM).^[1] It was a very weakmonoamine reuptake inhibitor, withIC₅₀Tooltip half-maximal inhibitory concentration values of 457,000 nM forserotonin, 160,000 nM fornorepinephrine, and 573,000 nM fordopamine.^[1]

Besides themonoamine receptors and transporters, biscaline showed affinity for the rattrace 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 producepsychedelic effects.^[1]

A variety of2C analogues and derivatives of biscaline have beensynthesized and studied, such as2C-Ph (2C-BI-1).^[1]

• Substituted mescaline analogue
• 4-PhPr-3,5-DMA
• 3C-BZ
• 4-Desoxymescaline

• Biscaline - Isomer Design

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