3C-BZ, also known as 4-benzyloxy-3,5-dimethoxyamphetamine or as 3C-benzscaline, is a lesser-known

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...

and a

substituted amphetamine Substituted amphetamines, or simply amphetamines, are a chemical class, class of compounds based upon the amphetamine structure; it includes all derivative (chemistry), derivative compounds which are formed by replacing, or substitution reacti ...

. 3C-BZ was first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

Use and effects

In Shulgin's book ''

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

'', the dosage range is listed as 25–200 mg and the duration as 18–24 hours.3C-BZ Entry in ''PiHKAL''
/ref> According to anecdotal reports from the substance's entry in PiHKAL, 3C-BZ's effects can vary significantly, ranging from intensified emotions and strange dreams, to effects similar to those of

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

or TMA.

Chemistry

Synthesis

3C-BZ was originally synthesized by Alexander Shulgin starting from 5-methoxy

eugenol Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, ...

(4-allyl-2,6-dimethoxyphenol) through a reaction with

benzyl chloride Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula . This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block. Preparation Benzyl chloride is prepared industrially ...

to form the benzyloxy derivative of 5-methoxyeugenol. The obtained benzyl derivative was reacted with tetranitromethane to form 1- -(benzyloxy)-3,5-dimethoxyphenyl2-nitro-1-propene, from which 3C-BZ is obtained by reduction of the nitropropene with

lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...

. Another possible synthetic route would be the reaction of benzyl chloride with

syringaldehyde Syringaldehyde is an organic compound that occurs in trace amounts widely in nature. Some species of insects use syringaldehyde in their chemical communication systems. ''Scolytus multistriatus'' uses it as a signal to find a host tree during ovip ...

to form 3,5-dimethoxy-4-benzyloxybenzaldehyde followed by condensation with

nitroethane Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor. Preparati ...

to form 1- -(benzyloxy)-3,5-dimethoxyphenyl2-nitro-1-propene. The obtained nitropropene can be reduced using lithium aluminium hydride, Red-Al, or an aluminium-mercury amalgam.

References

External links

3C-BZ - Isomer Design
{{Phenethylamines 3C (psychedelics) Benzyl compounds O-methylated phenols Psychedelic phenethylamines Substituted amphetamines

Use and effects

Chemistry

Synthesis

See also

References

External links