5-APB: Difference between revisions
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'''5-(2-Aminopropyl)benzofuran''' (commonly known as '''5-APB''') is a lesser-known novel [[Psychoactive class::entactogen]] of the [[chemical class::benzofuran]] class that produces [[MDA]]-like [[entactogenic]] and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is structurally related to entactogens like [[5-MAPB]], [[6-APB]], and [[MDA]]. | '''5-(2-Aminopropyl)benzofuran''' (commonly known as '''5-APB''') is a lesser-known novel [[Psychoactive class::entactogen]] of the [[chemical class::benzofuran]] class that produces [[MDA]]-like [[entactogenic]] and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is structurally related to entactogens like [[5-MAPB]], [[6-APB]], and [[MDA]]. | ||
5-APB was first synthesized in 1993 by psychedelic chemist and researcher [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]].<ref name="Nichols">Monte, A. P., Marona-Lewicka, D., Cozzi, N. V., | 5-APB was first synthesized in 1993 by psychedelic chemist and researcher [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]].<ref name="Nichols">{{cite journal | vauthors=((Monte, A. P.)), ((Marona-Lewicka, D.)), ((Cozzi, N. V.)), ((Nichols, D. E.)) | journal=Journal of Medicinal Chemistry | title=Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogs of 3,4-(methylenedioxy)amphetamine | volume=36 | issue=23 | pages=3700–3706 | date= November 1993 | url=https://pubs.acs.org/doi/abs/10.1021/jm00075a027 | issn=0022-2623 | doi=10.1021/jm00075a027}}</ref> However, it did not come into popular recreational use until over a decade later, where it briefly entered the rave scene and global research chemicals market. It was sold along with other novel benzofuran entactogens under the name "Benzofury" before its sale and import were subsequently banned.{{citation needed}} | ||
Compared to other members of its family such as [[6-APB]] and [[5-MAPB]], this compound in particular is known for its [[stimulating]] and [[euphoria|euphoric]] effects which has resulted in its rise in popularity as a product which is easily accessible through the use of online [[research chemical]] vendors. It has been commercially distributed as a [[designer drug]] alternative to [[MDMA]] since 2010.<ref>EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA | | Compared to other members of its family such as [[6-APB]] and [[5-MAPB]], this compound in particular is known for its [[stimulating]] and [[euphoria|euphoric]] effects which has resulted in its rise in popularity as a product which is easily accessible through the use of online [[research chemical]] vendors. It has been commercially distributed as a [[designer drug]] alternative to [[MDMA]] since 2010.<ref>{{Citation | title=EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA | url=https://www.emcdda.europa.eu/publications/implementation-reports/2010}}</ref> | ||
Very little data exists about the pharmacological properties, metabolism, and toxicity of 5-APB in humans, and it has only a brief history of human usage. It is highly advised that one take proper precautions, conduct [https://www.google.com independent research], and use proper [[harm reduction practices]] if choosing to use with this substance. | Very little data exists about the pharmacological properties, metabolism, and toxicity of 5-APB in humans, and it has only a brief history of human usage. It is highly advised that one take proper precautions, conduct [https://www.google.com independent research], and use proper [[harm reduction practices]] if choosing to use with this substance. | ||
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Human usage was not documented until 2010, when it emerged for sale on the [[research chemical]] market. It was particularly prominent in the UK "legal highs" market, where it was sold under the name "Benzofury".{{citation needed}} | Human usage was not documented until 2010, when it emerged for sale on the [[research chemical]] market. It was particularly prominent in the UK "legal highs" market, where it was sold under the name "Benzofury".{{citation needed}} | ||
On June 10, 2013 5-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.<ref>Advisory Council on the Misuse of Drugs, Jeremy Browne (4 June 2013). "Temporary class drug order on benzofury and NBOMe compounds - letter from ACMD". GOV.UK.</ref> On November 28, 2013 the ACMD recommended that 5-APB and related benzofurans should become Class B, Schedule 1 substances. On March 5, 2014 the UK Home Office announced that 6-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.<ref> | On June 10, 2013 5-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.<ref>Advisory Council on the Misuse of Drugs, Jeremy Browne (4 June 2013). "Temporary class drug order on benzofury and NBOMe compounds - letter from ACMD". GOV.UK.</ref> On November 28, 2013 the ACMD recommended that 5-APB and related benzofurans should become Class B, Schedule 1 substances. On March 5, 2014 the UK Home Office announced that 6-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.<ref>{{Citation | title=The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | url=https://www.legislation.gov.uk/uksi/2014/1106/made}}</ref> | ||
==Chemistry== | ==Chemistry== | ||
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==Pharmacology== | ==Pharmacology== | ||
{{pharmacology}} | {{pharmacology}} | ||
5-APB is a triple [[reuptake inhibitor]] for [[norepinephrine]], [[dopamine]] and [[serotonin]] as well as being an [[agonist]] for the [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] and [[Serotonin#The_5-HT_system|5-HT<sub>2B</sub>]] [[receptor]]s.<ref>The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat | 5-APB is a triple [[reuptake inhibitor]] for [[norepinephrine]], [[dopamine]] and [[serotonin]] as well as being an [[agonist]] for the [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] and [[Serotonin#The_5-HT_system|5-HT<sub>2B</sub>]] [[receptor]]s.<ref>{{cite journal | vauthors=((Dawson, P.)), ((Opacka-Juffry, J.)), ((Moffatt, J. D.)), ((Daniju, Y.)), ((Dutta, N.)), ((Ramsey, J.)), ((Davidson, C.)) | journal=Progress in Neuro-Psychopharmacology & Biological Psychiatry | title=The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat | volume=48 | pages=57–63 | date=3 January 2014 | issn=1878-4216 | doi=10.1016/j.pnpbp.2013.08.013}}</ref><ref>{{cite journal | vauthors=((Iversen, L.)), ((Gibbons, S.)), ((Treble, R.)), ((Setola, V.)), ((Huang, X.-P.)), ((Roth, B. L.)) | journal=European Journal of Pharmacology | title=Neurochemical profiles of some novel psychoactive substances | volume=700 | issue=1 | pages=147–151 | date=30 January 2013 | url=https://www.sciencedirect.com/science/article/pii/S0014299912010114 | issn=0014-2999 | doi=10.1016/j.ejphar.2012.12.006}}</ref> It has also been speculated that 5-APB acts as a [[releasing agent]] for the previously mentioned [[neurotransmitters]]. | ||
This means it effectively boosts the levels of the serotonin, norepinephrine and dopamine neurotransmitters in the brain by binding to and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the brain, resulting in [[stimulation|stimulating]] and [[physical euphoria|euphoric]] effects. | This means it effectively boosts the levels of the serotonin, norepinephrine and dopamine neurotransmitters in the brain by binding to and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the brain, resulting in [[stimulation|stimulating]] and [[physical euphoria|euphoric]] effects. | ||
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{{#ask: [[Category:5-APB]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:5-APB]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://www.erowid.org/experiences/subs/exp_5APB.shtml Erowid Experience Vaults: 5-APB] | |||
*[https://www.erowid.org/experiences/subs/exp_5APB.shtml Erowid Experience Vaults: 5-APB] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
{{DangerousInteractions/Stimulants|self=5-APB}} | {{DangerousInteractions/Stimulants|self=5-APB}} | ||
{{DangerousInteractions/MAOI|nt=dopamine}} | {{DangerousInteractions/MAOI|nt=dopamine}} | ||
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==Legal status== | ==Legal status== | ||
{{legalStub}} | {{legalStub}} | ||
*'''Brazil | |||
*'''United Kingdom | *'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref> | ||
*'''United States | *'''France''': 5-APB is classified as a narcotic since May 9, 2018, alongside other substances derived from benzofuran.<ref>{{cite web|url=https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000043529751|title=Article Annexe IV - Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants|publisher=Légifrance|access-date=September 23, 2022|language=fr}}</ref> | ||
*'''Germany''': 5-APB 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 18, 2019|language=de}}</ref> as of July 17, 2013.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?start=%2F%2F*%5B%40attr_id%3D%27bgbl113s2274.pdf%27%5D|title=Siebenundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 18, 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 18, 2019|language=de}}</ref> | |||
*'''Japan''': 5-APB is a controlled substance in Japan effective September 16th, 2015.<ref>[https://www.mhlw.go.jp/stf/houdou/0000097658.html "危険ドラッグの成分4物質を新たに指定薬物に指定"] (in Japanese). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved May 2, 2022.</ref> | |||
*'''The Netherlands:''' 5-APB is currently legal, but it is part of a substance group that may be banned soon as part of a recently passed law on New Psychoactive Substances (NPS). <ref>{{Citation|title= Wijziging van de Opiumwet in verband met het toevoegen van een derde lijst met als doel het tegengaan van de productie van en de handel in nieuwe psychoactieve stoffen en enkele andere wijzigingen (Dutch) | year=2024|url=https://www.tweedekamer.nl/kamerstukken/wetsvoorstellen/detail?id=2022Z14042&dossier=36159}}</ref> | |||
*'''Switzerland''': 5-APB is a controlled substance specifically named under Verzeichnis E.<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''': 5-APB is a Class B drug.{{citation needed}} | |||
*'''United States''': 5-APB could be considered an analogue of [[MDA]] and therefore would be covered under the Federal Analogue Act if intended for human consumption.{{citation needed}} | |||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Designer drug]] | *[[Designer drug]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/5-APB 5-APB (Wikipedia)] | *[https://en.wikipedia.org/wiki/5-APB 5-APB (Wikipedia)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=2359 5-APB (Isomer Design)] | *[https://isomerdesign.com/PiHKAL/explore.php?id=2359 5-APB (Isomer Design)] | ||
===Community=== | ===Community=== | ||
*[http://www.bluelight.org/vb/threads/548570-The-Big-amp-Dandy-5-APB-Thread The Big and Dandy 5-APB Thread (Bluelight)] | *[http://www.bluelight.org/vb/threads/548570-The-Big-amp-Dandy-5-APB-Thread The Big and Dandy 5-APB Thread (Bluelight)] | ||
==Literature== | ==Literature== | ||
* Greene, S. L. (2013). Benzofurans and benzodifurans. In Novel Psychoactive Substances (pp. 383-392). https://doi.org/10.1016/B978-0-12-415816-0.00016-X | |||
*Greene, S. L. (2013). Benzofurans and benzodifurans. In Novel Psychoactive Substances (pp. 383-392). https://doi.org/10.1016/B978-0-12-415816-0.00016-X | |||
==References== | ==References== | ||
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[[Category:Benzofuran]] | [[Category:Benzofuran]] | ||
[[Category:Amphetamine]] | [[Category:Amphetamine]] | ||
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