{{Short description|Psychoactive drug}} {{Drugbox | image = Butylone.svg | image_class = skin-invert-image | width = 225px | image2 = Butylone molecule ball.png | image_class2 = bg-transparent | width2 = 250px
<!-- Clinical data --> | tradename = | routes_of_administration = Oral<ref name="Oeri2021" /> | class = Serotonin releasing agent; Norepinephrine–dopamine reuptake inhibitor; Entactogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_DE = Anlage II | legal_US = Schedule I | legal_UK = Class B | legal_status = Illegal in Poland, Norway, Japan, Israel, Finland
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = 2–5 hours<ref name="Oeri2021" /> | excretion =
<!-- Identifiers --> | CAS_number = 802575-11-7 | PubChem = 56843046 | ChemSpiderID = 21073070 | UNII = X72T4EQ4FQ | synonyms = β-Keto-''N''-methylbenzodioxolylbutanamine; βk-MBDB; 3,4-Methylenedioxy-''N''-methyl-α-ethyl-β-ketophenethylamine
<!-- Chemical data --> | IUPAC_name = 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butan-1-one | C=12 | H=15 | N=1 | O=3 | SMILES = CCC(C(=O)C1=CC2=C(C=C1)OCO2)NC | StdInChI = 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 | StdInChIKey = CGKQZIULZRXRRJ-UHFFFAOYSA-N
<!-- Physical data --> | boiling_point = | density = }}
'''Butylone''', also known as '''β-keto-''N''-methylbenzodioxolylbutanamine''' ('''βk-MBDB'''), is a psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families.<ref name="Oeri2021">{{cite journal | vauthors = Oeri HE | title = Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy | journal = J Psychopharmacol | volume = 35 | issue = 5 | pages = 512–536 | date = May 2021 | pmid = 32909493 | pmc = 8155739 | doi = 10.1177/0269881120920420 | url = }}</ref> It is the β-keto (substituted cathinone) analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.
==Interactions== {{See also|MDMA#Interactions|Trip killer#Antidotes of other hallucinogens|MDMA/citalopram}}
==Pharmacology== ===Pharmacodynamics=== Butylone acts in a similar way as MDMA and methylone, it causes an increase in extracellular monoamine levels.<ref>{{cite journal | vauthors = Eshleman AJ, Wolfrum KM, Hatfield MG, Johnson RA, Murphy KV, Janowsky A | title = Substituted methcathinones differ in transporter and receptor interactions | journal = Biochemical Pharmacology | volume = 85 | issue = 12 | pages = 1803–1815 | date = June 2013 | pmid = 23583454 | pmc = 3692398 | doi = 10.1016/j.bcp.2013.04.004 }}</ref><ref name="pmid30345459">{{cite journal | vauthors = Saha K, Li Y, Holy M, Lehner KR, Bukhari MO, Partilla JS, Sandtner W, Sitte HH, Baumann MH | display-authors = 6 | title = The synthetic cathinones, butylone and pentylone, are stimulants that act as dopamine transporter blockers but 5-HT transporter substrates | journal = Psychopharmacology | volume = 236 | issue = 3 | pages = 953–962 | date = March 2019 | pmid = 30345459 | pmc = 6476708 | doi = 10.1007/s00213-018-5075-5 }}</ref><ref name="López"/>
The following tables lists the half maximal inhibitory and half maximal effective concentrations for norepinephrine, dopamine and serotonin receptors, respectively.<ref>{{cite journal | vauthors = Simmler LD, Buser TA, Donzelli M, Schramm Y, Dieu LH, Huwyler J, Chaboz S, Hoener MC, Liechti ME | display-authors = 6 | title = Pharmacological characterization of designer cathinones in vitro | journal = British Journal of Pharmacology | volume = 168 | issue = 2 | pages = 458–470 | date = January 2013 | pmid = 22897747 | pmc = 3572571 | doi = 10.1111/j.1476-5381.2012.02145.x }}</ref>
{| border="1" class="wikitable" |+ Monoamine transport inhibition, IC<sub>50</sub> (μM) ! NET | 2.02 (1.5–2.7) |- ! DAT | 2.90 (2.5–3.4) |- ! SERT | 6.22 (4.3–9.0) |}
{| border="1" class="wikitable" |+ Monoamine release, EC<sub>50</sub> (μM) ! DAT | >100 |- ! SERT | 5.5 (1.8–17) |- |}
===Pharmacokinetics=== ====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.<ref>{{cite journal | vauthors = Prosser JM, Nelson LS | title = The toxicology of bath salts: a review of synthetic cathinones | journal = Journal of Medical Toxicology | volume = 8 | issue = 1 | pages = 33–42 | date = March 2012 | pmid = 22108839 | pmc = 3550219 | doi = 10.1007/s13181-011-0193-z }}</ref>
class=skin-invert-image|600px|thumb|none|The three metabolic pathways of butylone.
==Chemistry== ===Synthesis=== Butylone can be synthesized 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.<ref name="López">{{cite journal | vauthors = López-Arnau R, Martínez-Clemente J, Pubill D, Escubedo E, Camarasa J | title = Comparative neuropharmacology of three psychostimulant cathinone derivatives: butylone, mephedrone and methylone | journal = British Journal of Pharmacology | volume = 167 | issue = 2 | pages = 407–420 | date = September 2012 | pmid = 22509960 | pmc = 3481047 | doi = 10.1111/j.1476-5381.2012.01998.x }}</ref>
[[File:ButyloneSyn.png|class=skin-invert-image|399x399px|thumb|none|A brief reaction mechanism for pentylone, a homologue of butylone.]]
==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.<ref>{{cite journal | vauthors = Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y | title = 年度買い上げ違法ドラッグ製品から検出されたデザイナードラッグ成分のNMRを中心とした分析 | trans-title = Analysis of designer drugs detected in the products purchased in fiscal year 2006 | language = ja | journal = Yakugaku Zasshi | volume = 128 | issue = 10 | pages = 1499–1505 | date = October 2008 | pmid = 18827471 | doi = 10.1248/yakushi.128.1499 | doi-access = free }}</ref> 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.<ref name="pmid19406592">{{cite journal | vauthors = Zaitsu K, Katagi M, Kamata HT, Kamata T, Shima N, Miki A, Tsuchihashi H, Mori Y | display-authors = 6 | title = Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine | journal = Forensic Science International | volume = 188 | issue = 1–3 | pages = 131–139 | date = July 2009 | pmid = 19406592 | doi = 10.1016/j.forsciint.2009.04.001 }}</ref>
==Society and culture== ===Legal status=== ====China==== As of October 2015 Butylone is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>
====Finland==== Scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>{{cite web | url=https://finlex.fi/fi/lainsaadanto/2014/1130 | title=FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014 }}</ref>
====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 {{lang|sv|Butylon, 1-(1,3-bensodioxol-5-yl)-2-(metylamino)butan-1-on}}.<ref>{{cite web | url=https://www.lakemedelsverket.se/sv/lagar-och-regler/foreskrifter/2022-48 | title=Föreskrifter (HSLF-FS 2022:48) om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika | publisher=LVFS | date=29 July 2022 | author=Christina Rångemark Åkerman | language=sv}}</ref>
====United States==== Butylone is also a Schedule I controlled substance under the Controlled Substances Act in the United States.
==See also== * Substituted methylenedioxyphenethylamine * Substituted cathinone * MDPBP * Pentylone * Ephylone
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/2042 Butylone - Isomer Design] * [https://psychonautwiki.org/wiki/Butylone Butylone - PsychonautWiki] * [https://www.erowid.org/chemicals/bk_mbdb/ bk-MBDB - Erowid] * [https://www.erowid.org/experiences/subs/exp_bk-MBDB.shtml βk-MBDB Reports - Erowid Experience Vault]
{{Entactogens}} {{Stimulants}} {{Monoamine releasing agents}} {{Phenethylamines}}
Category:Designer drugs Category:Entactogens Category:Methylenedioxycathinones Category:Norepinephrine-dopamine releasing agents Category:Phenylisobutylamines Category:Serotonin-norepinephrine-dopamine releasing agents