3C-BZ

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]

3C-BZ

Clinical data
Other names	4-Benzyloxy-3,5-methoxyamphetamine; 3,5-Methoxy-4-benzyloxyamphetamine; α-Methylbenzscaline; 3C-Benzscaline
Routes of administration	Oral[1][2][3]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	18–24 hours[1][2][3]
Identifiers
IUPAC name 1-[4-(benzyloxy)-3,5-dimethoxyphenyl]propan-2-amine
CAS Number	147947-26-0 Y
PubChem CID	44350160
ChemSpider	21106236 Y
UNII	FH79WY8EA2
ChEMBL	ChEMBL127871 Y
CompTox Dashboard (EPA)	DTXSID20658385
Chemical and physical data
Formula	C18H23NO3
Molar mass	301.386 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(N)Cc2cc(OC)c(OCc1ccccc1)c(c2)OC
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 Y Key:IQKPLBJGFPDASR-UHFFFAOYSA-N Y
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Use and effects

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

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

Chemistry

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.^[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

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

See also

• 3C (psychedelics)
• Benzscaline (BZ)
• Biscaline
• 4-PhPr-3,5-DMA
• 2C-T-33