Croweacin

Croweacin
Names
IUPAC name
4-methoxy-5-prop-2-enyl-1,3-benzodioxole
Other names
2-Methoxy-3,4-methylenedioxyphenylprop-2-ene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C11H12O3/c1-3-4-8-5-6-9-11(10(8)12-2)14-7-13-9/h3,5-6H,1,4,7H2,2H3
    Key: VGXJTTXSNPYTSK-UHFFFAOYSA-N
  • COC1=C(C=CC2=C1OCO2)CC=C
Properties
C11H12O3
Molar mass 192.214 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Croweacin is a naturally occurring allylbenzene and benzodioxole alkaloid found in Eriostemon crowei. Alexander Shulgin noted in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) that it can serve as a precursor in the chemical synthesis of the psychedelic amphetamine MMDA-3a, though Shulgin expressed that it is not a practical precursor. The synthesis of croweacin itself and its aldehyde have also been described. The compound was first described in the scientific literature by 1938.

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. "(5) The 2-methoxy-3,4-methylenedioxy pattern. This is the second of the three natural methoxy methylenedioxy orientations. Croweacin is 2-methoxy-3,4-methylenedioxyallylbenzene, and it takes its name from the binomial for the plant Eriostemon crowei from the worlds of rue and the citrus plants. It corresponds to the essential amphetamine MMDA-3a. This oil is found in plants of the Family Rutaceae." [...] "So, with two possible MMDA-3's it becomes reasonable, in fact essential, to name one of them "a" and the other "b". The "a" orientation occurs in nature as the essential oil croweacin, or 1-allyl-2-methoxy-3,4-methylenedioxybenzene. It thus can allow MMDA-3a to be classified as an Essential Amphetamine, since it can arise, in principle, by amination in the liver in vivo. But in the laboratory, croweacin is certainly not a practical starting material in this synthesis."
  2. 1 2 Baker, W.; Penfold, A. R.; Simonsen, J. L. (1939). "The structure and synthesis of croweacin". Journal of the Chemical Society: 439–443. doi:10.1039/JR9390000439.
  3. ↑ Shirasaka, Tadashi; Takuma, Yuki; Imaki, Naoshi (1990). "Preparation of 2-Methoxy-3,4-methylenedioxybenzaldehyde (Croweacin Aldehyde) from Pyrogallol". Synthetic Communications. 20 (8): 1213–1221. doi:10.1080/00397919008052830. ISSN 0039-7911. Retrieved 12 November 2026.
  4. ↑ Brownell, Wm. B.; Weston, Arthur W. (1951). "A New Synthesis of Croweacin Aldehyde". Journal of the American Chemical Society. 73 (10): 4971–4972. doi:10.1021/ja01154a507. ISSN 0002-7863. Retrieved 12 November 2026.
  5. ↑ Penfold, A. R.; Ramage, G. R.; Simonsen, J. L. (1938). "The constitution of croweacin". Journal of the Chemical Society: 756–758. doi:10.1039/JR9380000756.