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Exploring Dillapiole. To explore a different substance…

Names

Dillapiole
2,3-Dimethoxy-4,5-methylenedioxyphenylprop-2-ene

IUPAC names

4,5-Dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
4,5-Dimethoxy-6-(prop-2-en-1-yl)-1,3-benzodioxole

ID 1101 · Formula C₁₂H₁₄O₄ · Molecular weight 222.237

Tags Essential oil

InChI InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3

InChI Key LIKYNOPXHGPMIH-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES C=CCc1cc2OCOc2c(c1OC)OC

ChemSpider 9814
PubChem 10231
Wikidata Q419537
Wikipedia Dillapiole
Rhodium The complete book of ecstacy
Rhodium Manufacture of MDA analogs by Dal Cason (really comprehensive)
Rhodium Synthesis of dillapiole and 1,2,3,4-tetramethoxyallylbenzene (III)
Rhodium Syntheses of dillapiole and its 4-methylthio analog (1)

PiHKAL #59 DMMDA-2 · #157 TMA

Shulgin, AT. Possible implication of myristicin as a psychotropic substance. Nature, 1 Jan 1966, 210, 380–384. 707 kB. https://doi.org/10.1038/210380a0

Shulgin, AT; Sargent, T. Psychotropic phenylisopropylamines derived from apiole and dillapiole. Nature, 1 Jan 1967, 215, 1494–1495. 262 kB. https://doi.org/10.1038/2151494b0 #Dillapiole Rhodium.

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr. A, 1 Jan 1967, 30, 54–61. 769 kB. https://doi.org/10.1016/S0021-9673(00)84112-6 #XIa GC

Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB. #Dillapiole

Apiole

4,7-Dimethoxy-5-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole

Isoapiole

1102

Isodillapiole

1852

4-AlO-3,5-DMBAL · 4-Allyloxy-3,5-dimethoxybenzaldehyde

3,4-MeO-CPCA

6775

11026

pseudo-Dillapiole

7 Dec 2019 · · Isomer Design