| 词条 | Butylone | ||||||||||
| 释义 |
| IUPAC_name = 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butan-1-one | image = Bk-MBDB.svg | width = 240 | image2 = Butylone molecule ball.png | width2 = 260 | tradename = | legal_CA = Schedule I | legal_DE = Anlage II | legal_US = Schedule I | legal_UK = Class B | legal_status = Illegal in Poland, Norway, Japan, Israel, Finland | routes_of_administration = oral, intravenous, insufflation | metabolism = Hepatic | elimination_half-life = | excretion = Renal | CAS_number = 802575-11-7 | ATC_prefix = none | PubChem = 56843046 | ChemSpiderID = 21073070 | UNII = X72T4EQ4FQ | C=12 | H=15 | N=1 | O=3 | molecular_weight = 221.2524 g/mol | 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 | boiling_point = | density = }} Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine chemical class. It is the β-keto (substituted cathinone) analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone. HistoryButylone 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 MBDB as methylone 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] SynthesisButylone 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] MetabolismThere 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] Mechanism of actionButylone acts in a similar way as MDMA and Methylone, it causes an increase in extracellular monoamine levels.[5][3] The following tables lists the half maximal inhibitory and half maximal effective concentrations for norepinephrine, dopamine and serotonin receptors, respectively.[6]
Drug prohibition lawsChinaAs of October 2015 Butylone is a controlled substance in China.[7] SwedenSveriges 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.[8]United StatesButylone is also a Schedule I controlled substance under the Controlled Substances Act in the United States. See also
References1. ^{{cite journal | url=https://www.jstage.jst.go.jp/article/yakushi/128/10/128_10_1499/_article/-char/ja/ | title=2006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 | date=October 2008 | journal=Yakugaku Zasshi | vauthors=Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y | volume=128 | issue=10 | pages=1499–15505 | doi=10.1248/yakushi.128.1499 | pmid=18827471 | language=Japanese}} 2. ^{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0379073809001558 | title=Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine | date=July 2009 | journal=Forensic Science International | vauthors=Zaitsu K, Katagi M, Kamata HT, Kamata T, Shima N, Miki A, Tsuchihashi H, Mori Y | volume=188 | issue=1–3 | pages=131–139 | doi=10.1016/j.forsciint.2009.04.001 | pmid=19406592}} 3. ^1 {{cite journal | title=Comparative neuropharmacology of three psychostimulant cathinone derivatives: butylone, mephedrone and methylone | date=September 2012 | author=López, Arnau R. | author2=Martínez, Clemente J. | author3=Pubill D. | author4=Escubedo E. | author5=Camarasa J. | journal=British Journal of Pharmacology | volume=167 | issue=2 | pages=407–420 | doi=10.1111/j.1476-5381.2012.01998.x | pmc=3481047 | pmid=22509960}} 4. ^{{cite journal | doi=10.1007/s13181-011-0193-z | pmc=3550219 | title=The Toxicology of Bath Salts: A Review of Synthetic Cathinones | date=March 2012 | journal=Journal of Medical Toxicology | volume=8 | issue=1 | pages=33–42 | pmid=22108839 | vauthors=Prosser JM, Nelson LS}} 5. ^{{cite journal | doi=10.1016/j.bcp.2013.04.004 | pmc=3692398 | title=Substituted methcathinones differ in transporter and receptor interactions | journal=Biochemical Pharmacology | date=June 2013 | volume=85 | issue=12 | pages=1803–1815 | pmid=23583454 | vauthors=Eshleman AJ, Wolfrum KM, Hatfield MG, Johnson RA, Murphy KV, Janowsky A}} 6. ^{{cite journal | title=Pharmacological characterization of designer cathinones in vitro | author1=L. D. Simmler | author2=T. A. Buser | author3=M. Donzelli | author4=Y. Schramm | author5=L-H. Dieu | author6=J. Huwyler | author7=S. Chaboz | author8=M. C. Hoener | author9=M. E. Liechti | journal=British Journal of Pharmacology | date=January 2013 | volume=168 | issue=2 | pages=458–470 | doi=10.1111/j.1476-5381.2012.02145.x | pmid=22897747 | pmc=3572571 }} 7. ^{{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=Chinese | accessdate=1 October 2015}} 8. ^{{cite web | url=https://lakemedelsverket.se/upload/lvfs/LVFS_2010-1.pdf | title=Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika | publisher=LVFS | date=29 January 2010 | author=Christina Rångemark Åkerman | language=Swedish}} External links
6 : Psychedelic phenethylamines|Benzodioxoles|Cathinones|Designer drugs|Serotonin-norepinephrine-dopamine releasing agents|Entactogens and empathogens |
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