Osmorhizole

Osmorhizole
Names
IUPAC name
2,4-dimethoxy-1-prop-2-enylbenzene
Other names
2,4-Dimethoxyphenylprop-2-ene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)8-11(9)13-3/h4,6-8H,1,5H2,2-3H3
    Key: HZLYHZSHPUFYAR-UHFFFAOYSA-N
  • COC1=CC(=C(C=C1)CC=C)OC
Properties
C11H14O2
Molar mass 178.231 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Osmorhizole is a naturally occurring allylbenzene alkaloid found in carrot-like vegetables. In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin noted that it can serve as a precursor in the chemical synthesis of the stimulant and possible psychedelic amphetamine 2,4-dimethoxyamphetamine (2,4-DMA).

See also

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. "The 2,4-dimethoxy pattern. The 2,4-isomer is called osmorhizole, and the conjugated form is isoosmorhizole or nothosmyrnol; both are found in carrot-like vegetables. They, with ammonia, would give 2,4-DMA."
  2. ↑ Götz ME, Eisenreich A, Frenzel J, Sachse B, Schäfer B (May 2023). "Occurrence of Alkenylbenzenes in Plants: Flavours and Possibly Toxic Plant Metabolites". Plants (Basel). 12 (11). doi:10.3390/plants12112075. PMC 10255789. PMID 37299054.{{cite journal}}: CS1 maint: unflagged free DOI (link)