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]
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| Clinical data | |
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| Other names | 4-Phenyl-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-phenylphenethylamine |
| Drug class | Monoamine receptor modulator |
| Identifiers | |
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| Chemical and physical data | |
| Formula | C16H19NO2 |
| Molar mass | 257.333 g·mol−1 |
| 3D model (JSmol) | |
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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, NET, or DAT) at the assessed concentrations (Ki = >7,510–10,550 nM).[1] It was a very weak monoamine reuptake inhibitor, with IC50 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 = >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
editReferences
edit- ^ a b c d e f g h i j k 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.
External links
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