3C-BZ
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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).[1][2][3] It is the amphetamine (3C) analogue of benzscaline.[1][2][3] The drug was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1][2][3]
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| Other names | 4-Benzyloxy-3,5-methoxyamphetamine; 3,5-Methoxy-4-benzyloxyamphetamine; α-Methylbenzscaline; 3C-Benzscaline |
| Routes of administration | Oral[1][2][3] |
| Drug class | Serotonergic psychedelic; Hallucinogen |
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| Duration of action | 18–24 hours[1][2][3] |
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| Formula | C18H23NO3 |
| Molar mass | 301.386 g·mol−1 |
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Use and effects
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.[1][2][3] 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.[1]
Interactions
Chemistry
Synthesis
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.[1] 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.[1]
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]
History
3C-BZ was first described in the scientific literature by Alexander Shulgin and colleagues by 1978.[4][5] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1]
Society and culture
Legal status
Canada
3C-BZ is a controlled substance in Canada under phenethylamine blanket-ban language.[6]
United States
3C-BZ is not an explicitly controlled substance in the United States.[7] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.