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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.
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 aluminium 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 aluminium hydride, Red-Al, or an aluminium-mercury amalgam.
this, article, relies, largely, entirely, single, source, relevant, discussion, found, talk, page, please, help, improve, this, article, introducing, citations, additional, sources, find, sources, news, newspapers, books, scholar, jstor, september, 2019, benzy. This article relies largely or entirely on a single source Relevant discussion may be found on the talk page Please help improve this article by introducing citations to additional sources Find sources 3C BZ news newspapers books scholar JSTOR September 2019 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 3C BZ NamesPreferred IUPAC name 1 4 Benzyloxy 3 5 dimethoxyphenyl propan 2 amineOther names 4 Benzyloxy 3 5 methoxyamphetamineIdentifiersCAS Number 147947 26 0 Y3D model JSmol Interactive imageChEMBL ChEMBL127871 YChemSpider 21106236 YPubChem CID 44350160UNII FH79WY8EA2 YCompTox Dashboard EPA DTXSID20658385InChI 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 YKey IQKPLBJGFPDASR UHFFFAOYSA N YInChI 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 3H3Key IQKPLBJGFPDASR UHFFFAOYADSMILES CC N Cc2cc OC c OCc1ccccc1 c c2 OCPropertiesChemical formula C 18H 23N O 3Molar mass 301 386 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSynthesis edit3C 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 aluminium 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 aluminium hydride Red Al or an aluminium mercury amalgam References edit a b 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 Retrieved from https en wikipedia org w index php title 3C BZ amp oldid 1149766400, wikipedia, wiki, book, books, library,
