Butylone: Difference between revisions

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'''Butylone''' (also known as '''β-keto-''N''-methylbenzodioxolylbutanamine''', '''βk-MBDB''', or '''B1''') is a synthetic [[entactogen]] and [[psychoactive class::stimulant]] substance of the [[chemical class::cathinone]] class. It is the β-keto analog of [[MBDB]] and the substituted methylenedioxy analogue of [[buphedrone]].
'''Butylone''' (also known as '''β-keto-''N''-methylbenzodioxolylbutanamine''', '''βk-MBDB''', or '''B1''') is a synthetic [[entactogen]] and [[psychoactive class::stimulant]] substance of the [[chemical class::cathinone]] class. It is the β-keto analog of [[MBDB]] and the substituted methylenedioxy analogue of [[buphedrone]].


As a [[designer drug]], it is commonly sold on the street along with [[ethylone]] as a substitute or counterfeit for [[MDMA]] and [[methylone]] (all of which have collectively come to be referred to as "Molly") due to methylone's declining availability on the [[research chemical]] market. However, in spite of behavioral and pharmacological similarities between butylone and MDMA, the observed subjective effects of both substances are not completely identical. <ref name="urlCathinone | Ask Dr. Shulgin Online">{{cite web | url = http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm | title = Cathinone &#124; Ask Dr. Shulgin Online }}</ref>
As a [[designer drug]], it is commonly sold on the street along with [[ethylone]] as a substitute or counterfeit for [[MDMA]] and [[methylone]] (all of which have collectively come to be referred to as "Molly") due to methylone's declining availability on the [[research chemical]] market. However, in spite of behavioral and pharmacological similarities between butylone and MDMA, the observed subjective effects of both substances are not completely identical.<ref name="urlCathinone | Ask Dr. Shulgin Online">{{cite web | url = http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm | title = Cathinone &#124; Ask Dr. Shulgin Online }}</ref>


Subjective effects include [[stimulation]], [[thought acceleration]], [[motivation enhancement]], [[increased libido]], [[appetite suppression]], and [[euphoria]], Butylone is reported to be less potent than its relatives [[methylone]] and [[ethylone]] as well as possessing more classic [[stimulant]] as opposed to entactogenic effects.
Subjective effects include [[stimulation]], [[thought acceleration]], [[motivation enhancement]], [[increased libido]], [[appetite suppression]], and [[euphoria]], Butylone is reported to be less potent than its relatives [[methylone]] and [[ethylone]] as well as possessing more classic [[stimulant]] as opposed to entactogenic effects.
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==Pharmacology==
==Pharmacology==
Butylone acts as a mixed [[reuptake inhibitor]]/[[releasing agent]] of [[serotonin]], [[norepinephrine]], and [[dopamine]].<ref>Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135</ref><ref>The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811</ref> These are the [[neurotransmitters]] in charge of pleasure, reward, motivation and focus. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, essentially allowing them to accumulate and be reused, causing physically stimulating and euphoric effects.  
Butylone acts as a mixed [[reuptake inhibitor]]/[[releasing agent]] of [[serotonin]], [[norepinephrine]], and [[dopamine]].<ref>{{cite journal | vauthors=((Cozzi, N. V.)), ((Sievert, M. K.)), ((Shulgin, A. T.)), ((Jacob, P.)), ((Ruoho, A. E.)) | journal=European Journal of Pharmacology | title=Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines | volume=381 | issue=1 | pages=63–69 | date=17 September 1999 | issn=0014-2999 | doi=10.1016/s0014-2999(99)00538-5}}</ref><ref name="Nagai2007">{{cite journal | vauthors=((Nagai, F.)), ((Nonaka, R.)), ((Satoh Hisashi Kamimura, K.)) | journal=European Journal of Pharmacology | title=The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | volume=559 | issue=2 | pages=132–137 | date=22 March 2007 | url=https://www.sciencedirect.com/science/article/pii/S0014299906013811 | issn=0014-2999 | doi=10.1016/j.ejphar.2006.11.075}}</ref> These are the [[neurotransmitters]] in charge of pleasure, reward, motivation and focus. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, essentially allowing them to accumulate and be reused, causing physically stimulating and euphoric effects.  


In comparison to [[methylone]], it has approximately over 4x lower affinity for the norepinephrine transporter, while its affinity for the serotonin and dopamine transporters is similar.<ref>"Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf</ref><ref>The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811</ref> The results of these differences in pharmacology relative to [[MDMA]] is that butylone, like its close analog [[ethylone]] is less potent in terms of dose, has more balanced [[catecholaminergic]] effects relative to serotonergic, and behaves more like a [[reuptake inhibitor]] like [[methylphenidate]] than a releaser like [[amphetamine]]; however, butylone still has relatively robust releasing capabilities.<ref>"Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf</ref>
In comparison to [[methylone]], it has approximately over 4x lower affinity for the norepinephrine transporter, while its affinity for the serotonin and dopamine transporters is similar.<ref name="Simmler2013">{{cite journal | vauthors=((Simmler, L.)), ((Buser, T.)), ((Donzelli, M.)), ((Schramm, Y.)), ((Dieu, L.-H.)), ((Huwyler, J.)), ((Chaboz, S.)), ((Hoener, M.)), ((Liechti, M.)) | journal=British Journal of Pharmacology | title=Pharmacological characterization of designer cathinones in vitro: Pharmacology of cathinones | volume=168 | issue=2 | pages=458–470 | date= January 2013 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x | issn=00071188 | doi=10.1111/j.1476-5381.2012.02145.x}}</ref><ref name="Nagai2007"/> The results of these differences in pharmacology relative to [[MDMA]] is that butylone, like its close analog [[ethylone]] is less potent in terms of dose, has more balanced [[catecholaminergic]] effects relative to serotonergic, and behaves more like a [[reuptake inhibitor]] like [[methylphenidate]] than a releaser like [[amphetamine]]; however, butylone still has relatively robust releasing capabilities.<ref name="Simmler2013"/>


==Subjective effects==
==Subjective effects==
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===Psychosis===
===Psychosis===
{{Main|Stimulant psychosis}}
{{Main|Stimulant psychosis}}
Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref> A review on treatment for amphetamine, [[amphetamine|dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref><ref>Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.</ref> The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref> Psychosis very rarely arises from therapeutic use.<ref>Stimulant Misuse: Strategies to Manage a Growing Problem | http://www.acha.org/prof_dev/ADHD_docs/ADHD_PDprogram_Article2.pdf</ref><ref>http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf</ref>
Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref name="Shoptaw2009">{{cite journal | vauthors=((Shoptaw, S. J.)), ((Kao, U.)), ((Ling, W.)) | veditors=((Cochrane Drugs and Alcohol Group)) | journal=Cochrane Database of Systematic Reviews | title=Treatment for amphetamine psychosis | date=21 January 2009 | url=https://doi.wiley.com/10.1002/14651858.CD003026.pub3 | issn=14651858 | doi=10.1002/14651858.CD003026.pub3}}</ref> A review on treatment for amphetamine, [[amphetamine|dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref name="Shoptaw2009"/><ref>{{cite book | vauthors=((Hofmann, F. G.)) | date= 1983 | title=A handbook on drug and alcohol abuse: the biomedical aspects | publisher=Oxford University Press | edition=2nd ed | isbn=9780195030563}}</ref> The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref name="Shoptaw2009"/> Psychosis very rarely arises from therapeutic use.<ref>http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf</ref>
===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
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*'''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=Chinese | accessdate=1 October 2015}}</ref>
*'''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=Chinese | accessdate=1 October 2015}}</ref>
*'''Finland''': Butylone is a controlled substance.{{citation needed}}
*'''Finland''': Butylone is a controlled substance.{{citation needed}}
*'''France''': Butylone is scheduled as a "stupéfiant", i.e. a recognized drug of abuse. It is illegal to possess, buy, sell or manufacture.<ref>{{Citation | title=Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants  | url=https://www.legifrance.gouv.fr/loda/id/JORFTEXT000000533085/2020-11-20/}}</ref>
*'''Germany''': Butylone is controlled under Anlage II BtMG (''Narcotics Act, Schedule II'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html|title=Anlage II BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref> as of July 26, 2012.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?start=%2F%2F*%5B%40attr_id%3D%27bgbl112s1639.pdf%27%5D|title=Sechsundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 25, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref>
*'''Germany''': Butylone is controlled under Anlage II BtMG (''Narcotics Act, Schedule II'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html|title=Anlage II BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref> as of July 26, 2012.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?start=%2F%2F*%5B%40attr_id%3D%27bgbl112s1639.pdf%27%5D|title=Sechsundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 25, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref>
*'''Israel''': Butylone is a controlled substance.{{citation needed}}
*'''Israel''': Butylone is a controlled substance.{{citation needed}}
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*'''Sweden''': Butylone is a Schedule I controlled substance as of February 1, 2010.<ref>{{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=Läkemedelsverkets författningssamling|language=Swedish|access-date=December 25, 2019}}</ref>
*'''Sweden''': Butylone is a Schedule I controlled substance as of February 1, 2010.<ref>{{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=Läkemedelsverkets författningssamling|language=Swedish|access-date=December 25, 2019}}</ref>
*'''Switzerland''': Butylone is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''Switzerland''': Butylone is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United Kingdom''': Butylone is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.<ref>United Kingdom. (2010). Misuse of Drugs Act 1971 (S.I. 2010/1207). London: The Stationery Office Limited. Retrieved February 9, 2018, from https://www.legislation.gov.uk/uksi/2010/1207/made</ref>
*'''United Kingdom''': Butylone is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.<ref>{{Citation | title=The Misuse of Drugs Act 1971 (Amendment) Order 2010 | url=https://www.legislation.gov.uk/uksi/2010/1207/made}}</ref>
*'''United States''': Butylone is unscheduled in the United States. However it could be considered an analog of [[methylone]] or [[MDMA]], thus making it illegal under the scope of the Federal Analog Act.{{citation needed}}
*'''United States''': Butylone is unscheduled in the United States. However it could be considered an analog of [[methylone]] or [[MDMA]], thus making it illegal under the scope of the Federal Analog Act.{{citation needed}}


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<references />
<references />


[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Stimulant]]
[[Category:Stimulant]]
[[Category:Entactogen]]
[[Category:Entactogen]]
[[Category:Phenethylamine]]
[[Category:Amphetamine]]
[[Category:MDxx]]
[[Category:MDxx]]
[[Category:Cathinone]]
[[Category:Cathinone]]
[[Category:Research chemical]]
[[Category:Research chemical]]


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