Phenylacetone is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbol ...

C₆H₅CH₂COCH₃. It is a colorless oil that is soluble in

organic solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

s. This substance is used in the manufacture of methamphetamine and amphetamine, where it is commonly known as P2P. Due to the illicit uses in

clandestine chemistry Clandestine chemistry is chemistry carried out in secret, and particularly in illegal drug laboratories. Larger labs are usually run by gangs or organized crime intending to produce for distribution on the black market. Smaller labs can be run b ...

, it was declared a

schedule II controlled substance The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States ...

in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

in 1980. In humans, phenylacetone occurs as a metabolite of amphetamine and methamphetamine via

FMO3 Flavin-containing monooxygenase 3 (FMO3), also known as dimethylaniline monooxygenase -oxide-forming3 and trimethylamine monooxygenase, is a flavoprotein enzyme () that in humans is encoded by the ''FMO3'' gene. This enzyme catalyzes the follow ...

-mediated oxidative deamination.

Synthesis

One method of creating phenylacetone is via: : phenylacetic acid (C₈H₈O₂) + acetic anhydride (C₄H₆O₃) +

pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a ...

catalyst → phenylacetone (C₉H₁₀O) +

carbon dioxide Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is trans ...

(CO₂) +

water Water (chemical formula ) is an Inorganic compound, inorganic, transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living ...

(H₂O)

Sodium acetate Sodium acetate, CH3COONa, also abbreviated Na O Ac, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses. Applications Biotechnological Sodium acetate is used as the carbon source for culturing bacteria ...

has been used instead of pyridine. In the 20th century

chloroacetone Chloroacetone is a chemical compound with the chemical formula, formula . At Standard conditions for temperature and pressure, STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour. It wa ...

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

, and anhydrous

aluminum chloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contam ...

were used to synthesize phenylacetone.https://pubs.acs.org/doi/10.1021/ja01863a506 62, 6, 1622. https://doi.org/10.1021/ja01863a506 The reaction included Friedel–Crafts alkylation.

Amphetamine metabolism

In popular culture

In the TV series '' Breaking Bad'', Walter White manufactures methamphetamine through an enantioselective variation of the P2P method, starting from phenylacetone.

Notes

Reference notes

References