Butylone
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| Other names | Îē-Keto-N-methylbenzodioxolylbutanamine; Îēk-MBDB; 3,4-Methylenedioxy-N-methyl-Îą-ethyl-Îē-ketophenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonin releasing agent; Norepinephrineâdopamine reuptake inhibitor; Entactogen |
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| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Duration of action | 2â5 hours[1] |
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| Chemical and physical data | |
| Formula | C12H15NO3 |
| Molar mass | 221.256 g·molâ1 |
| 3D model (JSmol) | |
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Butylone, also known as Îē-keto-N-methylbenzodioxolylbutanamine (Îēk-MBDB), is a psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families.[1] It is the Îē-keto (substituted cathinone) analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.
Interactions
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]Butylone acts in a similar way as MDMA and methylone, it causes an increase in extracellular monoamine levels.[2][3][4]
The following tables lists the half maximal inhibitory and half maximal effective concentrations for norepinephrine, dopamine and serotonin receptors, respectively.[5]
| NET | 2.02 (1.5â2.7) |
|---|---|
| DAT | 2.90 (2.5â3.4) |
| SERT | 6.22 (4.3â9.0) |
| DAT | >100 |
|---|---|
| SERT | 5.5 (1.8â17) |
Pharmacokinetics
[edit]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 Îē-ketone reduction into Îē-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.[6]
Chemistry
[edit]Synthesis
[edit]Butylone can be synthesized via the following route: 3,4-methylenedioxybutyrophenone dissolved in dichloromethane to bromine gives 3âē,4âē-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.[4]
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 sold as a designer drug.[7] 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.[8]
Society and culture
[edit]Legal status
[edit]China
[edit]As of October 2015 Butylone is a controlled substance in China.[9]
Finland
[edit]Scheduled in the "government decree on psychoactive substances banned from the consumer market".[10]
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 2022:48 listed as Butylon, 1-(1,3-bensodioxol-5-yl)-2-(metylamino)butan-1-on.[11]
United States
[edit]Butylone is also a Schedule I controlled substance under the Controlled Substances Act in the United States.
See also
[edit]References
[edit]- 1 2 3 Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512â536. doi:10.1177/0269881120920420. PMCÂ 8155739. PMIDÂ 32909493.
- â Eshleman AJ, Wolfrum KM, Hatfield MG, Johnson RA, Murphy KV, Janowsky A (June 2013). "Substituted methcathinones differ in transporter and receptor interactions". Biochemical Pharmacology. 85 (12): 1803â1815. doi:10.1016/j.bcp.2013.04.004. PMCÂ 3692398. PMIDÂ 23583454.
- â Saha K, Li Y, Holy M, Lehner KR, Bukhari MO, Partilla JS, et al. (March 2019). "The synthetic cathinones, butylone and pentylone, are stimulants that act as dopamine transporter blockers but 5-HT transporter substrates". Psychopharmacology. 236 (3): 953â962. doi:10.1007/s00213-018-5075-5. PMC 6476708. PMID 30345459.
- 1 2 LÃģpez-Arnau R, MartÃnez-Clemente J, Pubill D, Escubedo E, Camarasa J (September 2012). "Comparative neuropharmacology of three psychostimulant cathinone derivatives: butylone, mephedrone and methylone". British Journal of Pharmacology. 167 (2): 407â420. doi:10.1111/j.1476-5381.2012.01998.x. PMCÂ 3481047. PMIDÂ 22509960.
- â Simmler LD, Buser TA, Donzelli M, Schramm Y, Dieu LH, Huwyler J, et al. (January 2013). "Pharmacological characterization of designer cathinones in vitro". British Journal of Pharmacology. 168 (2): 458â470. doi:10.1111/j.1476-5381.2012.02145.x. PMC 3572571. PMID 22897747.
- â Prosser JM, Nelson LS (March 2012). "The toxicology of bath salts: a review of synthetic cathinones". Journal of Medical Toxicology. 8 (1): 33â42. doi:10.1007/s13181-011-0193-z. PMCÂ 3550219. PMIDÂ 22108839.
- â Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (October 2008). "åđīåšĶčē·ãäļãéæģããĐãã°čĢ―åããæĪåšãããããķãĪããžããĐãã°æåãŪNMRãäļåŋãĻããåæ" [Analysis of designer drugs detected in the products purchased in fiscal year 2006]. Yakugaku Zasshi (in Japanese). 128 (10): 1499â1505. doi:10.1248/yakushi.128.1499. PMID 18827471.
- â Zaitsu K, Katagi M, Kamata HT, Kamata T, Shima N, Miki A, et al. (July 2009). "Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine". Forensic Science International. 188 (1â3): 131â139. doi:10.1016/j.forsciint.2009.04.001. PMID 19406592.
- â "å ģäšå°åãéčŊįĻįąŧéšŧéčŊååįēūįĨčŊååįŪĄåæģãįéįĨ" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
- â "FINLEX ÂŪ - Ajantasainen lainsÃĪÃĪdÃĪntÃķ: Valtioneuvoston asetus kuluttajamarkkinoiltaâĶ 1130/2014".
- â Christina RÃĨngemark à kerman (29 July 2022). "FÃķreskrifter (HSLF-FS 2022:48) om ÃĪndring i LÃĪkemedelsverkets fÃķreskrifter (LVFS 2011:10) om fÃķrteckningar Ãķver narkotika" (in Swedish). LVFS.
