Desoxybromoscaline (DBR), also known as 4-bromo-3,5-dimethoxyphenethylamine (4-Br-3,5-DMPEA) or as 4-bromomescaline, is a serotonin receptor modulator of the phenethylamine and desoxyscaline families related to the psychedelic drug mescaline. "A mescaline analogue with a bromo atom in place of the 4-methoxyl group is an analogue of mescaline in exactly the same way that DOB (a very potent amphetamine) is an analog of TMA-2 (the original trisubstituted amphetamine). This analogue, 3,5-dimethoxy-4-bromoamphetamine 4-bromo-3,5-dimethoxyphenethylamine, has been found to be a most effective serotonin agonist, and it is a possibility that it could be a most potent phenethylamine. But, as of the present time, it has never been assayed in man." Data table It is the analogue of mescaline in which the methoxy group at the 4 position has been replaced with a bromine atom. The drug is also the phenethylamine (α-desmethyl) analogue of 4-Br-3,5-DMA and a positional isomer of 2C-B (4-Br-2,5-DMPEA).
Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin briefly mentions desoxybromoscaline and states that it has never been tested in humans. As such, its properties and effects in humans are unknown.
Pharmacology Pharmacodynamics Desoxybromoscaline has been found to be a potent serotonin receptor agonist in the sheep umbilical artery ( = 185nM). It was 7.6-fold more potent than mescaline in this assay. In a subsequent study, the drug showed high affinity for the serotonin 5-HT2A receptor (K0.5 = 45nM). Its affinity for this receptor was approximately 18-fold higher than that of mescaline. Later on, the activities of desoxybromoscaline have been further described, with it showing affinity for all three serotonin 5-HT2 receptors and acting as a full agonist of the serotonin 5-HT2A receptor and as a partial agonist of the serotonin 5-HT2B receptor.
Chemistry Synthesis The chemical synthesis of desoxybromoscaline has been described.
Analogues Analogues of desoxybromoscaline include mescaline, desoxy (desoxymescaline; 4-desoxymescaline; 4-methylmescaline; 4-Me-3,5-DMPEA), 4-O-desmethylmescaline (desmethyl; 4-hydroxymescaline; 4-OH-3,5-DMPEA), 2C-B (4-Br-2,5-DMPEA), and 4-Br-3,5-DMA, among others. 4-Br-3,5-DMA has been found to be a potent psychoactive drug in humans, though it did not produce clear hallucinogenic effects at tested doses of 3 to 10mg orally and instead produced pronounced analgesic and tactile anesthetic effects among others. On the other hand, desoxy (4-methylmescaline), a positional isomer of 2C-D, is a psychedelic drug similarly to mescaline at doses of 40 to 120mg orally, albeit with distinct effects. Daniel Trachsel has expressed great interest in desoxyscalines like desoxymescaline and desoxybromoscaline and has named and studied many of these compounds.
History Desoxybromoscaline was first described in the scientific literature by David E. Nichols and Alexander Shulgin and colleagues in 1977. Subsequently, it was described by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.
See also Desoxyscaline 3C-DBR (4-Br-3,5-DMA)
References
External links 4-Br-3,5-DMPEA - Isomer Design