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3C-BZ

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3C-BZ
Clinical data
Other names4-Benzyloxy-3,5-methoxyamphetamine; 3,5-Methoxy-4-benzyloxyamphetamine; α-Methylbenzscaline; 3C-Benzscaline
Routes of
administration		Oral[1][2][3]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action18–24 hours[1][2][3]
Identifiers
  • 1-[4-(benzyloxy)-3,5-dimethoxyphenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H23NO3
Molar mass301.386 g·mol−1
3D model (JSmol)
  • CC(N)Cc2cc(OC)c(OCc1ccccc1)c(c2)OC
  • 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
  (verify)

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]

Use and effects

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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

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Chemistry

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Synthesis

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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

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3C-BZ was first described in the scientific literature by Alexander Shulgin and colleagues by 1978.[4][5]

See also

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References

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  1. ^ a b c d e f g h i Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 3C-BZ Entry in PiHKAL
  2. ^ a b c d e f Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 705, 717, 736. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 31 January 2025. Die Substanz Benzscalin (BZ; 61) [69, 82] wurde bis anhin im Menschen offiziell nicht evaluiert. Jedoch wuide diese Substanz von der Gesellschaft für chemische Industrie in Basel im Jahre 1931 patentiert und sollte zu therapeutischen Zwecken Verwendung finden [82]. Der Fakt, dass sein Amphetamin- oder 3C-Gegenstück 3C-BZ (100) seine Aktivität im Menschen mit einer großen Unsicherheit bezüglich der Dosis zeigte (25-200mg; n=10) [19] veranlasste bis anhin nicht dazu, weitere Untersuchungen am BZ (61) zu tätigen. Vielleicht trägt hier der genetische Polymorphismus zu einem stark unterschiedlich ausgeprägten Metabolismus der Benzylgruppe bei. Wäre die Substanz 3C-BZ (100) eine potente, klar definierte Substanz gewesen, so ließen sich dutzende neue aktive Verbindungen herstellen [19] und man könnte mit großen und kleinen sowie elektronenziehenden und -stoßenden Gruppen am Aromaten die Wirkung modulieren. Die Substanz Phescalin (PH; 60) wurde bis anhin nicht beschrieben; im Falle interessanter pharmakologischen Eigenschaften ließe sich auch hier der Einfluss diverser Substituenten am Phenoxyring prüfen. Große, Iipophile Substituenten in der 4-Position haben bei den 2,4,5-trisubstituierten Phenylalkylaminen zu 5-HT2A-Rezcptorantagonisten geführt. Dies könnte auch hier der Fall sein, das wurde jedoch bis anhin nicht abgeklärt.
  3. ^ a b c d e f Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol. 12 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010. Since the amphetamine homolog 3C-BZ induces psychedelic effects similar to LSD (3) or TMA (6) (Shulgin and Shulgin 1991), [benzscaline (BZ)] (33) may induce psychedelic effects as well, based on its similar structure and high binding affinity at the 5-HT2A receptor.
  4. ^ Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.
  5. ^ Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline Analogs: Substitutions at the 4-Position" (PDF). In Barnett G, Trsic M, Willette RE (eds.). QuaSAR: Quantitative Structure Activity Relationships Of Analgesics, Narcotic Antagonists, And Hallucinogens (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 22. National Institute on Drug Abuse. pp. 27–37. PMID 101882.
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