Butylone

Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is a psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families. It is the β-keto (substituted cathinone) analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.

Butylone

Clinical data
Routes of administration	oral, intravenous, insufflation
ATC code	none
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I Illegal in Poland, Norway, Japan, Israel, Finland
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butan-1-one
CAS Number	802575-11-7
PubChem CID	56843046
ChemSpider	21073070
UNII	X72T4EQ4FQ
CompTox Dashboard (EPA)	DTXSID001024651
Chemical and physical data
Formula	C12H15NO3
Molar mass	221.256 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(C(=O)C1=CC2=C(C=C1)OCO2)NC
InChI InChI=1S/C12H15NO3/c1-3-9(13-2)12(14)8-4-5-10-11(6-8)16-7-15-10/h4-6,9,13H,3,7H2,1-2H3 Key:CGKQZIULZRXRRJ-UHFFFAOYSA-N

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.^[1] Butylone shares the same relationship to methylone as MBDB does to MDMA ("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 methylone.^[2]

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.^[3]

A brief reaction mechanism for pentylone, a homologue of butylone.

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.^[4]

The three metabolic pathways of butylone.

Mechanism of action

Butylone acts in a similar way as MDMA and Methylone, it causes an increase in extracellular monoamine levels.^[5][6][3]

The following tables lists the half maximal inhibitory and half maximal effective concentrations for norepinephrine, dopamine and serotonin receptors, respectively.^[7]

Monoamine transport inhibition, IC₅₀ (μM)

NET	2.02 (1.5–2.7)
DAT	2.90 (2.5–3.4)
SERT	6.22 (4.3–9.0)

Monoamine release, EC₅₀ (μM)

DAT	>100
SERT	5.5 (1.8–17)

Drug prohibition laws

China

As of October 2015 Butylone is a controlled substance in China.^[8]

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".^[9]

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 Butylon, 1-(1,3-bensodioxol-5-yl)-2-(metylamino)butan-1-on.^[10]

United States

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

See also

• MDPBP
• Pentylone
• Ephylone