3,4-Methylenedioxypropiophenone

3,4-Methylenedioxypropiophenone, also known as 3,4-(Methylenedioxy)phenyl-1-propanone (MDP1P), is a phenylpropanoid found in some plants of the genus Piper and is an isomer of 3,4-methylenedioxyphenyl-2-propanone (MDP2P).

3,4-Methylenedioxypropiophenone
Chemical structure of 3,4-methylenedioxypropiophenone
Names
Preferred IUPAC name
1-(2H-1,3-Benzodioxol-5-yl)propan-1-one
Other names
1-(Benzo[d][1,3]dioxol-5-yl)propan-1-one
1-(1,3-Benzodioxol-5-yl)-1-propanone
5-Propionyl-1,3-benzodioxole
MDP1P
Identifiers
3D model (JSmol)
165729
ChemSpider
ECHA InfoCard 100.044.473
EC Number
  • 248-937-6
UNII
  • InChI=1S/C10H10O3/c1-2-8(11)7-3-4-9-10(5-7)13-6-12-9/h3-5H,2,6H2,1H3 checkY
    Key: RVBJGSPBFIUTTR-UHFFFAOYSA-N checkY
  • CCC(=O)C1=CC2=C(C=C1)OCO2
Properties
C10H10O3
Molar mass 178.187 g·mol−1
Density 1.21 g/mL
Melting point 37 °C (99 °F; 310 K)
Boiling point 291 °C
Hazards
Safety data sheet (SDS) MSDS at Sigma Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Natural occurrence

Studies of various chemotypes of Piper marginatum have either detected this compound to be the dominant constituent of the plant's essential oil or absent from it altogether.[1][2] Of 22 samples collected from South America, specimens from the following regions had the greatest amount of the chemical by dry leaf mass: Manaus (0.35%), Melgaço (0.348%), Belterra (0.33%), Monte Alegre (0.241 to 0.266%), and Alta Floresta (0.123%).[2]

Uses

MDP1P is a can be used as a precursor in the synthesis of methylone and various other substituted methylenedioxy- phenethylamine derivatives. It can be prepared via a Grignard reaction between ethylmagnesium bromide and piperonylonitrile.

United States

MDP1P is not a scheduled drug at the federal level in the United States nor is it on the DEA list of chemicals.[3]

Florida

"3,4-methylenedioxy-propiophenone" along with "2-Bromo-3,4-Methylenedioxypropiophenone" and "3,4-methylenedioxy-propiophenone-2-oxime" are Schedule I controlled substances in the state of Florida making them illegal to buy, sell, or possess in Florida.[4]

References
  1. Ramos, L.S.; Silva, M.L.; Luz, A.I.R.; Zoghbi, M.G.B.; Maia, J. G. S. (1986). "Essential Oil of Piper marginatum". Journal of Natural Products. 49 (4): 712–713. doi:10.1021/np50046a033.
  2. Andrade, Eloisa Helena; Carreirab, Lea Maria; Silva, Milton Helio; Silva, Joao Domingos; Bastos, Cleber N.; Sousae, Pergentino Jose; Guimaraes, Elsie F.; Maia, Jose Guilherme (2008). "Variability in Essential-Oil Composition of Piper marginatum sensu lato". Chemistry & Biodiversity. 5 (1): 197–208. doi:10.1002/cbdv.200890011. PMID 18205123.
  3. "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  4. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.