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).
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 |
|
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
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 [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Natural occurrence
editStudies 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
editMDP1P 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.
Legal status
editUnited States
editMDP1P is not a scheduled drug at the federal level in the United States nor is it on the DEA list of chemicals.[3]
Florida
edit"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
edit- ^ 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.
- ^ a b 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. S2CID 25177229.
- ^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
- ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL