Butylone

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Butylone
Bk-MBDB.svg
Butylone molecule ball.png
Systematic (IUPAC) name
1-(1,3-benzodioxol-5-yl)-2-(methylamino)butan-1-one
Clinical data
Legal status
  • Illegal in The United Kingdom, I-P(Poland), Norway, Japan, Israel, Finland[1]
Routes oral, intravenous, insufflation
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
CAS number 17762-90-2
ATC code None
ChemSpider 21073070
Chemical data
Formula C12H15NO3 
Molecular mass 221.2524 g/mol
Physical data
Density 1.2 [2] g/cm3
Boiling point 362.2[3] °C (684.0 °F)

Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (bk-MBDB), is an entactogen, psychedelic, and stimulant of the phenethylamine chemical class. It is the β-keto analogue of MBDB.

History[edit]

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 synthesized by a chemical supply company, and has since continued to be sold as a research chemical.[4] It has since been explored as a possible entheogen. Butylone shares the same relationship to MBDB as methylone does to MDMA ("Ecstasy"). The dosage range is not fully understood but seems to be lower than for MBDB. 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.[5]

Synthesis[edit]

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. [6]


Metabolism[edit]

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. [7] [8]


Uses[edit]

The compound butylone is significantly used as a recreational drug. Reports exist for a different number of methods to consume it. [9]

Orally[edit]

Oral use of butylone is the least damaging and intrusive method. Oral doses last long but also take longer to get started.

Insufflation[edit]

Snorting seems to be worse when compared to taking the same dose orally.

Intravenous[edit]

Injection in the blood stream is known. But just like intravenous use of other drugs it increases the risks.

Effects[edit]

The effects of butylone have not been described in any scientific literature. Some drug forums report personal experiences with butylone. The experiences are similar to methylone and ethylone: euphoria, stimulation, mental sharpness and a warm safe feeling. However the doses planned to be used is exceeded most of the time. The effects last for 10-12 hours with headaches , loss of sleep and appetite afterwards. [10]

Drug prohibition laws[edit]

Sweden[edit]

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 2010:1 listed as Butylon, 1-(1,3-bensodioxol-5-yl)-2-(metylamino)butan-1-on.[11]

United States[edit]

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

See also[edit]

References[edit]

  1. ^ = WDU20111050614 "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011. 
  2. ^ |https://crystalrows.com/pc/butylone
  3. ^ |https://crystalrows.com/pc/butylone
  4. ^ Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y. Analysis of designer drugs detected in the products purchased in fiscal year 2006. (Japanese). Yakugaku Zasshi. 2008 Oct;128(10):1499-505. PMID 18827471
  5. ^ Zaitsu K, Katagi M, Kamata HT, Kamata T, Shima N, Miki A, Tsuchihashi H, Mori Y (July 2009). "Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine". Forensic Science International 188 (1–3): 131–9. doi:10.1016/j.forsciint.2009.04.001. PMID 19406592. 
  6. ^ López‐Arnau, R., Martínez‐Clemente, J., Pubill, D., Escubedo, E. and Camarasa, J. (2012), Comparative neuropharmacology of three psychostimulant cathinone derivatives: butylone, mephedrone and methylone. British Journal of Pharmacology, 167: 407–420. doi:10.1111/j.1476-5381.2012.01998.x
  7. ^ http://ac.els-cdn.com/S0379073809001558/1-s2.0-S0379073809001558-main.pdf?_tid=edcf700c-c317-11e4-948b-00000aacb35f&acdnat=1425547007_5f64d00dfe02a6528abac4461bf954a2
  8. ^ http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3550219/
  9. ^ https://drugs-forum.com/forum/showwiki.php?title=Butylone
  10. ^ http://www.soft-tox.org/files/Designer_Drugs/Butylone.pdf
  11. ^ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010-1.pdf

External links[edit]