Butylone, also known as β-keto-''N''-methylbenzodioxolylbutanamine (βk-MBDB), is a

psychoactive drug A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

, phenylisobutylamine, and

cathinone Cathinone (; also known as β-ketoamphetamine) is a monoamine alkaloid found in the shrub ''Catha edulis'' (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to t ...

families. It is the β-keto (

substituted cathinone Substituted cathinones, or simply cathinones, which include some stimulants and Empathogen-entactogen, entactogens, are chemical derivative, derivatives of cathinone. They feature a substituted phenethylamine, phenethylamine core with an alkyl ...

) analogue of MBDB and the

substituted methylenedioxyphenethylamine The substituted methylenedioxyphenethylamines (abbreviated as MDxx) represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous Psychoactive drug, psychoactive substances with Empathogen, entac ...

analogue of buphedrone.

History

Butylone was first synthesized by Koeppe, Ludwig and Zeile which is mentioned in their 1967 paper. It remained an obscure product of academia until 2005 when it was sold as a

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...

. Butylone shares the same relationship to

methylone Methylone, also known as 3,4-methylenedioxy-''N''-methylcathinone (MDMC), is an entactogen and stimulant drug of the amphetamine, cathinone, and benzodioxole families related to 3,4-methylenedioxymethamphetamine (MDMA; "ecstasy"). It is th ...

as MBDB does to

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...

("Ecstasy"). Formal research on this chemical was first conducted in 2009, when it was shown to be metabolised in a similar manner to related drugs like

Synthesis

Butylone can be synthesized in a laboratory via the following route: 3,4-methylenedioxybutyrophenone dissolved in dichloromethane to bromine gives 3′,4′-methylenedioxy-2-bromobutyrophenone. This product was then dissolved in dichloromethane and added to an aqueous solution of methylamine (40%). HCl was then added. The aqueous layer was removed and made alkaline by using sodium bicarbonate. For the extraction of the amine ether was used. To get butylone a drop of ether and HCl solution was added. ButyloneSyn

Metabolism

There are three major metabolic pathways of bk-MBDB as shown in the figure. As result of demethylenation followed by O-methylation bk-MBDB metabolises into 4-OH-3-MeO and 3-OH-4-MeO metabolites in human urine. The second pathway is a β-ketone reduction into β-ketone reduced metabolites. The third pathway is a N-dealkylation into N-dealkyl metabolites. The first two pathways occur more than pathway three. The most common metabolite is the 4-OH-3-MeO metabolite. The metabolites containing a hydroxyl-group would be excreted as their conjugates in urine. ButyloneMetabolism

Mechanism of action

Butylone acts in a similar way as MDMA and Methylone, it causes an increase in extracellular monoamine levels. The following tables lists the half maximal inhibitory and half maximal effective concentrations for norepinephrine, dopamine and serotonin receptors, respectively.

Drug prohibition laws

China

As of October 2015 Butylone is a controlled substance in China.

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".

Sweden

''Sveriges riksdag'' added butylone to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as narcotics in Sweden as of Feb 1, 2010, published by ''Medical Products Agency'' in their regulation LVFS 2022:48 listed as .

United States

Butylone is also a Schedule I controlled substance under the Controlled Substances Act in the United States.

References

External links

Erowid βk-MBDB Vault

Erowid βk-MBDB Experience Vault
{{Phenethylamines Cathinones Designer drugs Entactogens Methylenedioxyphenethylamines Norepinephrine-dopamine releasing agents Phenylisobutylamines Serotonin-norepinephrine-dopamine releasing agents