3C-BZ

3C-BZ
Names
Preferred IUPAC name
1-[4-(Benzyloxy)-3,5-dimethoxyphenyl]propan-2-amine
Other names
4-Benzyloxy-3,5-methoxyamphetamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C18H23NO3/c1-13(19)9-15-10-16(20-2)18(17(11-15)21-3)22-12-14-7-5-4-6-8-14/h4-8,10-11,13H,9,12,19H2,1-3H3 checkY
    Key: IQKPLBJGFPDASR-UHFFFAOYSA-N checkY
  • InChI=1/C18H23NO3/c1-13(19)9-15-10-16(20-2)18(17(11-15)21-3)22-12-14-7-5-4-6-8-14/h4-8,10-11,13H,9,12,19H2,1-3H3
    Key: IQKPLBJGFPDASR-UHFFFAOYAD
SMILES
  • CC(N)Cc2cc(OC)c(OCc1ccccc1)c(c2)OC
Properties
Chemical formula
 C18H23NO3
Molar mass 301.386 g·mol−1
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 (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.[1] 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. 1 2 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 3C-BZ Entry in PiHKAL
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