Biscaline
Biscaline, also known as 3,5-dimethoxy-4-phenylphenethylamine, is a monoamine receptor modulator of the phenethylamine family. It is the analogue of mescaline in which the methoxy group at the 4 position has been replaced with a phenyl ring.
The drug shows affinity for the serotonin 5-HT1A receptor. Conversely, it did not bind to the serotonin 5-HT2A, 5-HT2B, or 5-HT2C receptors at the assessed concentrations. It is said to have lacked activational effects on the serotonin 5-HT2A and 5-HT2B receptors at the assessed concentrations. Biscaline also bound to the α2A-adrenergic receptor, but not to the α1A-adrenergic receptor, the dopamine D2 receptor, or the monoamine transporters at the assessed concentrations. It was a very weak monoamine reuptake inhibitor, with values of 457,000nM for serotonin, 160,000nM for norepinephrine, and 573,000nM for dopamine.
Besides the monoamine receptors and transporters, biscaline showed affinity for the rat trace amine-associated receptor 1 , but not for the mouse TAAR1 and did not activate the human TAAR1. Biscaline's interaction with the α2A-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-HT2A 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.