3C-BZ

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3C-BZ
3C-BZ-2D-Skeletal.svg
3C-BZ-3d-sticks.png
Names
IUPAC name
1-(4-benzyloxy-3,5-methoxyphenyl)propan-2-amine
Other names
4-Benzyloxy-3,5-methoxyamphetamine
Identifiers
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL127871 YesY
ChemSpider
  • 21106236 YesY
PubChem CID
  • 44350160
Properties
C18H23NO3
Molar mass 301.39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

3C-BZ, or 4-benzyloxy-3,5-dimethoxyamphetamine, is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 25–200 mg, and the duration as 18–24 hours. 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 or TMA.[1] 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-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 aluminum 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 aluminum hydride, Red-Al, or an aluminum-mercury amalgam.

References

  1. ^ Shulgin, Alexander; Ann Shulgin (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 

External links

  • 3C-BZ Entry in PiHKAL
  • 3C-BZ Entry in PiHKAL • info
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