3,4-Methylenedioxyphenylpropan-2-one

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3,4-Methylenedioxyphenylpropan-2-one
MDP2P.svg
Names
Preferred IUPAC name
1-(2H-1,3-Benzodioxol-5-yl)propan-2-one
Other names
3,4-methylenedioxyphenyl-2-propanone
1-(1,3-benzodioxol-5-yl)propan-2-one
piperonyl methyl ketone
3,4-methylenedioxyphenylacetone
Identifiers
3D model (JSmol)
AbbreviationsMDP2P, PMK
ChemSpider
ECHA InfoCard 100.022.843 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H10O3/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5H,4,6H2,1H3 Yes check.svgY
    Key: XIYKRJLTYKUWAM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H10O3/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5H,4,6H2,1H3
    Key: XIYKRJLTYKUWAM-UHFFFAOYAA
  • O=C(C)Cc1ccc2OCOc2c1
Properties
C10H10O3
Molar mass 178.185 g/mol
AppearanceYellowish green liquid (when impure)
Density 1.211 g/cm3
Boiling point 290 °C (554 °F; 563 K)
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3,4-Methylenedioxyphenylpropan-2-one [1] or piperonyl methyl ketone (MDP2P or PMK) is a chemical compound consisting of a phenylacetone moiety substituted with a methylenedioxy functional group. It is commonly synthesized from either safrole (which, for comparison, is 3-[3,4-(methylenedioxy)phenyl]-2-propene) or its isomer isosafrole via oxidation using the Wacker oxidation or peroxyacid oxidation methods. MDP2P is unstable at room temperature and must be kept in the freezer in order to be preserved properly.

MDP2P is a precursor in the chemical synthesis of the methylenedioxyphenethylamine (MDxx) class of compounds, the classic example of which is 3,4-methylenedioxy-N-methylamphetamine (MDMA), and is also an intermediate between the MDxx family and their slightly more distant precursor safrole or isosafrole. On account of its relation to the MDxx chemical class, MDP2P, as well as safrole and isosafrole, are in the United States (U.S.) Drug Enforcement Administration (DEA) List I of Chemicals of the Controlled Substances Act (CSA) via the Chemical Diversion and Trafficking Act (CDTA). It is also considered a category 1 precursor in the European Union.

See also

Related Research Articles

<span class="mw-page-title-main">MDMA</span> Psychoactive drug, often called ecstasy

3,4-Methyl​enedioxy​methamphetamine (MDMA), commonly known as ecstasy, and molly or mandy, is a potent empathogen–entactogen with stimulant and minor psychedelic properties. Investigational indications include as an adjunct to psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."

<span class="mw-page-title-main">Safrole</span> Chemical compound

Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">Misuse of Drugs Act (Singapore)</span> Law of Singapore

The Misuse of Drugs Act 1973 is a statute of the Parliament of Singapore that enables authorities to prosecute offenders for crimes involving illegal drugs. The law is designed specifically to grant the Government of Singapore, through its agencies such as the Central Narcotics Bureau, enforcement powers to combat offences such as the trafficking, importation or exportation, possession, and consumption of controlled drugs.

<span class="mw-page-title-main">Piperonal</span> Chemical compound

Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.

<span class="mw-page-title-main">Phenylacetone</span> Chemical compound

Phenylacetone, also known as phenyl-2-propanone, is an organic compound with the chemical formula C6H5CH2COCH3. It is a colorless oil that is soluble in organic solvents. It is a mono-substituted benzene derivative, consisting of an acetone attached to a phenyl group. As such, its systematic IUPAC name is 1-phenyl-2-propanone.

Phenylacetones are a group of organic compounds containing a phenyl moiety and an acetone moiety bonded together, the archetypal example being phenylacetone.

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

<span class="mw-page-title-main">Isosafrole</span> Chemical compound

Isosafrole is an organic compound that is used in the fragrance industry. Structurally, the molecule is related to allylbenzene, a type of aromatic organic chemical. Its fragrance is reminiscent of anise or licorice. It is found in small amounts in various essential oils, but is most commonly obtained by isomerizing the plant oil safrole. It exists as two geometric isomers, cis-isosafrole and trans-isosafrole.

<span class="mw-page-title-main">Phenyl-2-nitropropene</span> Chemical compound

1-Phenyl-2-nitropropene, or simply phenyl-2-nitropropene, or P2NP, as it is commonly referred to, is a chemical compound from the aromatic group of compounds, with the formula C9H9NO2. It is a light-yellow crystalline solid with a distinct smell. Phenyl-2-nitropropene is used in the pharmaceutical industry to manufacture the drug Adderall, an amphetamine mixture used to treat ADHD and narcolepsy. P2NP and other similar nitrostyrenes are also employed in the clandestine manufacture of drugs of the amphetamine class, and are listed as drug precursors in many countries.

<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.

<span class="mw-page-title-main">DMMDA</span> Psychedelic drug

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book PiHKAL. Shulgin listed the dosage as 30–75 mg and the duration as 6–8 hours. He reported DMMDA as producing LSD-like images, mydriasis, ataxia, and time dilation.

3,4-Methylenedioxy-<i>N</i>-ethylamphetamine Chemical compound

3,4-Methylenedioxy-N-ethylamphetamine is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.

<span class="mw-page-title-main">Piperic acid</span> Chemical compound

Piperic acid is a chemical often obtained by the base-hydrolysis of the alkaloid piperine from black pepper, followed by acidification of the corresponding salt. Piperic acid is an intermediate in the synthesis of other compounds such as piperonal, and as-such may be used to produce fragrances, perfumes flavorants and drugs as well as other useful compounds.

1,3-Benzodioxole (1,2-methylenedioxybenzene) is an organic compound with the formula C6H4O2CH2. The compound is classified as benzene derivative and a heterocyclic compound containing the methylenedioxy functional group. It is a colorless liquid.

European law on illicit drug precursors:

Drug precursors, also referred to as precursor chemicals or simply precursors, are substances used to manufacture illicit drugs. Most precursors also have legitimate commercial uses and are legally used in a wide variety of industrial processes and consumer products, such as medicines, flavourings, and fragrances.

<span class="mw-page-title-main">5-MAPDB</span> Chemical compound

5-MAPDB (1-(2,3-dihydrobenzofuran-5-yl)-N-methylpropan-2-amine) is a chemical compound which acts as an entactogenic drug. It is structurally related to drugs like 5-APDB and 5-MAPB, which have similar effects to MDMA and have been used as recreational drugs. 5-MAPDB has been studied to determine its pharmacological activity, and was found to be a relatively selective serotonin releaser, though with weaker actions as a releaser of other monoamines and 5-HT2 receptor family agonist, similar to older compounds such as 5-APDB.

<span class="mw-page-title-main">3,4-Methylenedioxypropiophenone</span> Chemical compound

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).

References