3C-BZ (4-benzyloxy-3,5-dimethoxyamphetamine) is a lesser-known

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

and a

substituted amphetamine Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with sub ...

. 3C-BZ was first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...

. In his book '' PiHKAL'', 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 (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, vi ...

or TMA. Very little data exists about the pharmacological properties, metabolism, and toxicity of 3C-BZ.

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, basil ...

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

benzyl chloride Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block. Preparation Benzyl chloride is prepared indust ...

to form the benzyloxy derivative of 5-methoxyeugenol. The obtained benzyl derivative was reacted with

tetranitromethane Tetranitromethane or TNM is an organic oxidizer with chemical formula . Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric acid. ...

to form 1- -(Benzyloxy)-3,5-dimethoxyphenyl2-nitro-1-propene, from which 3C-BZ is obtained by reduction of the nitropropene with

lithium aluminum hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li Al H4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic sy ...

. 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 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

Red-Al Sodium bis(2-methoxyethoxy)aluminium hydride (SMEAH; trade names Red-Al, Synhydrid, Vitride) is a complex hydride reductant with the chemical formula, formula NaAlH2(OCH2CH2OCH3)2. The trade name Red-Al refers to its being a ''red''ucing ''al''um ...

, or an aluminum-mercury amalgam.

References

{{Hallucinogenic phenethylamines O-methylated phenols Psychedelic phenethylamines Substituted amphetamines