3C-BZ

3C-BZ, also known as 4-benzyloxy-3,5-dimethoxyamphetamine or as α-methylbenzscaline (3C-benzscaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA). It is the amphetamine (3C) analogue of benzscaline. The drug was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose range is listed as 25 to 200 mg and the duration as 18 to 24 hours. The effects of 3C-BZ have been reported to vary significantly, ranging from intensified emotions and strange dreams, to effects similar to those of other psychedelics like LSD or TMA.

3C-BZ was originally synthesized by Alexander Shulgin starting from 5-methoxyeugenol (4-allyl-2,6-dimethoxyphenol) through a reaction with benzyl chloride to form the benzyloxy derivative of 5-methoxyeugenol. The obtained benzyl derivative was reacted with tetranitromethane to form 1-[4-(benzyloxy)-3,5-dimethoxyphenyl]-2-nitro-1-propene, from which 3C-BZ is obtained by reduction of the nitropropene with lithium aluminium hydride.

Another possible synthetic route would be the reaction of benzyl chloride with syringaldehyde to form 3,5-dimethoxy-4-benzyloxybenzaldehyde followed by condensation with nitroethane to form 1-[4-(benzyloxy)-3,5-dimethoxyphenyl]-2-nitro-1-propene. The obtained nitropropene can be reduced using lithium aluminium hydride, Red-Al, or an aluminium-mercury amalgam.^{[citation needed]}

3C-BZ was first described in the scientific literature by Alexander Shulgin and colleagues by 1978.