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Abstract
Piperonyl methyl ketone serves as a foundational component or transitional stage in the creation of methylenedioxy phenethylamines and amphetamines, such as 3,4-MDMA. It may exist as an unintended inclusion within formulations of methylenedioxy phenethylamines. The precise physiological and toxicological characteristics of this compound remain undisclosed.
This piece provides an extensive examination of MDP2P, encompassing its basic details, physico-chemical attributes, Chemical Reactions of MDP2P, legal standing, synthesis of MDP2P, concluding remarks, and bibliography.
General Information About MDP2P [1-4]
Other synonyms names of MDP2P are: Methyl piperonyl ketone; Piperonyl Methyl Ketone; Piperonylmethylketone; 3,4-Methylenedioxyphenyl-2-propanone; 3,4-Methylenedioxyphenyl acetone; 5-Acetonyl-1,3-benzodioxole; 3,4-Methylenedioxybenzyl methyl ketone; 1-(1,3-benzodioxol-5-yl)-2-propanone; PMK Oil; Piperonylactone;
IUPAC Name of MDP2P: 1-(1,3-benzodioxol-5-yl)propan-2-one
CAS number is 4676-39-5
Physico-Chemical Properties of MDP2P [1-4]
- Molecular Formula C10H10O3
- Molar Weight 178.18 g/mol
- Boiling point 270.41°C (rough estimate)
- Melting Point 87-88 °C
- Refractive index 1.547
- Solubility: DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; Methanol: 10 mg/ml; PBS (pH 7.2): 3 mg/ml
- Color/Form: yellow liquid
- Odor: sweet
- The substance is unstable at room temperature and should be stored in a freezer.
Structural formula present on Figure 1.
Liquid possible of the MDP2P can be seen in the picture provided in Figure 2.
Chemical Information of MDP2P [5-7]
MDP2P (3,4-methylenedioxy-phenyl-2-propanone) is a unique chemical compound composed of phenylacetone with a methylenedioxy functional group substitution. It serves as a vital chemical precursor for MDMA (commonly referred to as “Ecstasy”), MDEA, and other related substances. Notably, it is currently listed on the watch list of the DEA.
Transparent liquids or crystalline substances, aromatic aldehydes, and ketones often possess the distinct aroma of bitter almonds and flowers. Their spectral characteristics bear resemblance to unsaturated carbonyl compounds, while chemically they share similarities with saturated aliphatic compounds. Aromatic compounds, influenced by the aromatic ring, exhibit lower reactivity compared to aliphatic compounds. Their reactions primarily occur through the benzene ring.
Aromatic aldehydes and ketones possess toxic properties and demonstrate irritant and localized effects. They can permeate the skin, especially in the case of unsaturated aliphatic compounds. Certain substances within this category have carcinogenic and mutagenic effects. Halogen derivatives of ketones induce severe irritation of mucous membranes and cause burns upon skin contact. Alicyclic ketones display narcotic effects.
Ketones play a crucial role in the metabolic processes of living organisms. For instance, ubiquinone participates in oxidative-reductive reactions within tissue respiration. Compounds containing the ketone functional group include essential monosaccharides (such as fructose), terpenes (menthone, carvone), components of essential oils (such as camphor and jasmine), natural dyes (indigo, alizarin, flavonoids), steroid hormones (cortisone, progesterone), musk (muskone), and the antibiotic tetracycline.
The presence of an excessive amount of ketones in an individual’s urine and blood indicates ketosis or ketoacidosis, which may be associated with abnormalities in carbohydrate metabolism or related pathological processes.
Chemical Reactions of MDP2P
Given that MDP2P falls under the category of aromatic ketones, its potential participation in the subsequent reactions can be explored:
The interaction between MDP2P and halogens, as illustrated in Figure 3.
Interaction with Sodium Hydrosulfite Figure 4.
Upon heating with a solution of sodium carbonate or mineral acid, hydrosulfite derivatives decompose with the release of free ketone, as depicted in Figure 5.
Formation of Schiff Bases, which are impurities in MDMA synthesis, and their interaction with ammonia and its derivatives. The interaction of oxo compounds with ammonia and its derivatives proceeds through a mechanism of addition-elimination, forming a C=N bond. In the initial stage, a nucleophile attaches to the carbon of the carbonyl group C=O. However, compounds containing two electron-accepting groups on a single carbon atom are unstable and tend to stabilize by cleaving a water molecule. The reaction yields a final product called an azomethine (substituted imine) or Schiff base. See Figure 6.
Clemmensen Reduction. Clemmensen reduction is a reaction that involves the reduction of a ketone using zinc amalgam in concentrated hydrochloric acid under heating. The actual reagent in this process is the nascent hydrogen generated during the reaction. As a result, the carbonyl group is reduced to a methylene group. See Figure 7.
Grignard Reaction. The Grignard reaction is a fundamental reaction that involves the reaction of ketones with organomagnesium compounds, serving as the basis for the synthesis of tertiary alcohols. See Figure 8.
Mannich Aminomethylation. Mannich aminomethylation is a three-component condensation reaction involving a ketone, formaldehyde, and a secondary amine. See Figure 9.
Reductive Amination. Figure 10
Legal Status
MDP2P in the United States is classified as List I, a precursor substance. List I designates substances that have a high potential for being used in the illegal production of drugs. MDP2P, also known as 3,4-methylenedioxyphenyl-2-propanone, is closely regulated and monitored due to its significant role in the synthesis of illicit drugs such as MDMA (ecstasy) and methamphetamine. Its inclusion in List I signifies the recognition of its potential for misuse and the need to control its availability to prevent illicit drug manufacturing.
At the international level, the United Nations categorizes MDP2P under Precursors Table I. This classification system is used to identify substances that can be employed in the illicit production of drugs. By categorizing MDP2P in Precursors Table I, the UN acknowledges its significance as a precursor in the global context and emphasizes the importance of international cooperation in monitoring and controlling its distribution.
In the European Union, MDP2P falls under Category 1 Precursor. This designation highlights the EU’s commitment to regulating substances with a high potential for misuse in drug manufacturing. By classifying MDP2P as a Category 1 Precursor, the EU aims to prevent the diversion of this substance towards illicit drug production within its member states and ensure the safety and well-being of its citizens.
Synthesis of 1-(1,3-benzodioxol-5-yl)propan-2-one [8, 9]
It is synthesized from safrole or its isomer isosafrole by oxidation using the Wacker process or by oxidation with peroxycarboxylic acids. 3,4-MDP-2-P can also be synthesized from heliotropin (also known as piperonal or 3,4-methylenedioxybenzaldehyde) – initially, condensation is carried out with nitroethane, followed by the reduction of the resulting nitropropene to the ketone. Reaction schemes are shown in Figure 11 and Figure 12.
Conclusion
MDP2P (3,4-methylenedioxyphenyl-2-propanone) is a precursor substance that plays a significant role in the illicit production of drugs such as MDMA (ecstasy) and methamphetamine. It is synthesized from safrole or its isomer isosafrole through processes like the Wacker oxidation or oxidation with peroxycarboxylic acids. MDP2P can also be synthesized from piperonal (3,4-methylenedioxybenzaldehyde) through condensation with nitroethane followed by reduction. The regulation and control of MDP2P, categorized as List I in the United States, Precursors Table I by the United Nations, and Category 1 Precursor in the European Union, are crucial for preventing its diversion into the illegal drug trade and ensuring public safety.
Bibliography
- https://en.wikipedia.org/wiki/3,4-Methylenedioxyphenylpropan-2-one
- https://pubchem.ncbi.nlm.nih.gov/compound/78407
- https://www.chemspider.com/Chemical-Structure.70776.html
- https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5471135.htm
- https://bbgate.com/threads/mdma-synthesis-via-nabh4-from-mdp2p.5188/
- Justin Cormick, James F. Carter Stable isotope characterisation of 3,4-methylenedioxyphenyl-2-propanone and 3,4-methylenedioxyamphetamine prepared from piperonal. Rapid Communications in Mass Spectrometry, 2022, Volume 37, Issue 4. https://doi.org/10.1002/rcm.9446 https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/abs/10.1002/rcm.9446
- Ryan Gallagher, Ronald Shimmon Synthesis and impurity profiling of MDMA prepared from commonly available starting materials. Forensic Science International, 2012, Volume 223, Issues 1–3, pp. 306-313. https://doi.org/10.1016/j.forsciint.2012.10.006 https://www.sciencedirect.com/science/article/abs/pii/S0379073812004604
- https://bbgate.com/threads/mdp2p-pmk-total-synthesis-via-safrole.884/
- https://en.wikipedia.org/wiki/Wacker_process