3C-BZ
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Names | |
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Preferred IUPAC name
1-[4-(Benzyloxy)-3,5-dimethoxyphenyl]propan-2-amine | |
Other names
4-Benzyloxy-3,5-methoxyamphetamine
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
PubChemCID
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UNII | |
CompTox Dashboard(EPA)
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Properties | |
C18H23NO3 | |
Molar mass | 301.386g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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3C-BZ(4-benzyloxy-3,5-dimethoxyamphetamine) is a lesser-knownpsychedelic drugand asubstituted amphetamine.3C-BZ was first synthesized byAlexander Shulgin.In his bookPiHKAL,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 ofLSDorTMA.[1]Very little data exists about the pharmacological properties, metabolism, and toxicity of 3C-BZ.
Synthesis[edit]
3C-BZ was originally synthesized by Alexander Shulgin starting from 5-methoxyeugenol(4-allyl-2,6-dimethoxyphenol) through a reaction withbenzyl chlorideto form the benzyloxy derivative of 5-methoxyeugenol.[1]The obtained benzyl derivative was reacted withtetranitromethaneto form 1-[4-(benzyloxy)-3,5-dimethoxyphenyl]-2-nitro-1-propene, from which 3C-BZ is obtained by reduction of the nitropropene withlithium aluminium hydride.
Another possible synthetic route would be the reaction of benzyl chloride withsyringaldehydeto form 3,5-dimethoxy-4-benzyloxybenzaldehyde followed by condensation withnitroethaneto 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.
References[edit]
- ^abcShulgin, Alexander;Shulgin, Ann(September 1991).PiHKAL: A Chemical Love Story.Berkeley, California:Transform Press.ISBN0-9630096-0-5.OCLC25627628.3C-BZ Entry inPiHKAL
Phenethylamines |
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Amphetamines |
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Phentermines |
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Catecholamines (and close relatives) |
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Psychedelics (5-HT2A agonists) |
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