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{{SummarySheet}}
{{SubstanceBox/5-APB}}
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'''5-APB''' (also known as '''5-(2-aminopropyl)benzofuran''', '''1-benzofuran-5-ylpropan-2-amine''', or '''benzofury''') is a [[psychoactive class::stimulant]] and [[Psychoactive class::entactogen]]ic drug of the [[chemical class::phenethylamine]] and [[chemical class::benzofuran]] class.


This compound 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 certain online [[research chemical]] vendors. It has been sold as a [[designer drug]] since 2010.<ref>EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA | http://www.emcdda.europa.eu/publications/implementation-reports/2010</ref>
'''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">{{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>{{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.
 
==History and culture==
{{historyStub}}
The synthesis of 5-APB was first reported by a team led by the medicinal chemist and psychedelic researcher [[David E. Nichols]] at Purdue University. They were examining the role of the MDA dioxle ring structure in  interacting with serotonergic neurons. It was also partly an effort to find an alternative to [[MDMA]], which was gaining recognition as a potentially useful adjunct in psychotherapy, but was also being linked to neurotoxic effects.<ref name="Nichols" />
 
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>{{Citation | title=The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | url=https://www.legislation.gov.uk/uksi/2014/1106/made}}</ref>


5-APB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass so doses should be adjusted accordingly.
==Chemistry==
==Chemistry==
5-APB is a benzofuran and phenethylamine, so it has an ethylamine chain and a furan ring attached to the main benzene ring. It can also be classified as an amphetamine derivative because the ethylamine chain is alpha methylated. Molecules of the amphetamine class contain a [[phenethylamine]] core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>. The oxygen in the furan ring is placed at the 5 position, which generally constitutes more stimulating effects than when the oxygen is placed at the 6 position, which is usually described as being more [[psychedelic]] in effects.
{{chemistry}}
5-(2-aminopropyl)benzofuran, also known as 5-APB, is a [[benzofuran]] and [[phenethylamine]], meaning it has an ethylamine chain and a furan ring attached to the core benzene ring. It can also be classified as an amphetamine derivative because the ethylamine chain is alpha methylated. Molecules of the amphetamine class contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>. The oxygen in the furan ring is placed at the 5 position, which generally constitutes more stimulating effects than when the oxygen is placed at the 6 position, which is usually described as being more [[psychedelic]] in effects. 5-APB is commonly found as the succinate and hydrochloride salt.{{citation needed}} The hydrochloride salt is 10% more potent by mass so doses should be adjusted accordingly.


==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 (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/24012617?dopt=Abstract</ref><ref>Neurochemical profiles of some novel psychoactive substances (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299912010114</ref> It has also been speculated that 5-APB acts as a [[releasing agent]] for the previously mentioned [[neurotransmitters]].
{{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>{{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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==Subjective effects==
==Subjective effects==
{{effectStub}}
{{effectStub}}
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.                                                                           
{{Preamble/SubjectiveEffects}}                                                                           
===Physical effects===
{{effects/base
|{{effects/physical|
*'''[[Effect::Stimulation]]'''
*'''[[Effect::Stimulation]]'''
*'''[[Effect::Abnormal heartbeat]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Muscle contractions]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Nausea]]'''  
*'''[[Effect::Nausea]]'''  
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Increased perspiration]]'''


===Cognitive effects===
}}
*'''[[Effect::Empathy, love, and sociability enhancement]]'''
{{effects/aftereffects|
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Memory enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Cognitive euphoria|Euphoria]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Increased music appreciation]]'''
 
===Visual effects===
*'''[[Effect::Acuity enhancement]]'''
===After effects===
The effects which occur during the [[offset]] of a [[stimulant]] experience generally feel negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and occurs because of [[neurotransmitter]] depletion. Its effects commonly include:
The effects which occur during the [[offset]] of a [[stimulant]] experience generally feel negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and occurs because of [[neurotransmitter]] depletion. Its effects commonly include:
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety]]'''
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*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Wakefulness]]'''
}}
|{{effects/cognitive|
*'''[[Effect::Empathy, affection, and sociability enhancement]]'''
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Memory enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
}}
}}
===Experience reports===
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
{{#ask: [[Category:5-APB]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
*[https://www.erowid.org/experiences/subs/exp_5APB.shtml Erowid Experience Vaults: 5-APB]


==Toxicity and harm potential==
==Toxicity and harm potential==
{{Main|Research chemicals#Toxicity and harm potential}}
{{Further|Research chemicals#Toxicity and harm potential}}
The toxicity and long-term health effects of recreational 5-APB use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because 5-APB has very little history of human usage. Anecdotal evidence from people who have tried 5-APB within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).  
The toxicity and long-term health effects of recreational 5-APB use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because 5-APB has very little history of human usage.  


Its agonism for 5-HT2B makes it likely that 5-APB would be cardiotoxic with long-term use, as seen in other 5-HT2B agonists such as [[fenfluramine]] and [[MDMA]].
Anecdotal evidence from people who have tried 5-APB within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).  


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
5-APB's high affinity for the 5-HT2b receptor makes it likely that 5-APB would be cardiotoxic with long-term use, as seen in other 5-HT2B agonists such as [[fenfluramine]] and [[MDMA]].
 
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
===Tolerance and addiction potential===
===Tolerance and addiction potential===
As with other [[stimulant]]s, the chronic use of 5-APB can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.
As with other [[stimulant]]s, the chronic use of 5-APB can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.
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===Psychosis===
===Psychosis===
{{Main|Stimulant psychosis}}
{{Main|Stimulant psychosis}}
Abuse of compounds within the amphetamine chemical 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]]). A review on treatment for amphetamine, [[dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely. The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis. Psychosis very rarely arises from therapeutic use.
Abuse of compounds within the amphetamine chemical 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]]). A review on treatment for amphetamine, [[amphetamine|dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely. The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis. Psychosis very rarely arises from therapeutic use.
 
===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Stimulants|self=5-APB}}
{{DangerousInteractions/Stimulants|self=5-APB}}
{{DangerousInteractions/MAOI|nt=dopamine}}
{{DangerousInteractions/MAOI|nt=dopamine}}
*'''[[Stimulants]]''' - The neurotoxic effects of 5-APB may be increased when combined with other stimulants.
 
*'''[[Cocaine]]''' - This combination may increase strain on the heart.
====[[Serotonin syndrome]] risk====
====[[Serotonin syndrome]] risk====
{{DangerousInteractions/SerotoninSyndrome}}
{{DangerousInteractions/SerotoninSyndrome}}


==Legal issues==
==Legal status==
{{legalStub}}
{{legalStub}}
*'''U.K.''' - 5-APB is a Class B drug.
 
*'''U.S.''' - 5-APB could be considered an analogue of [[MDA]] and therefore would be covered under the Federal Analogue Act if intended for human consumption.
*'''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>
*'''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]]
*[[Psychedelics]]
*[[Designer drug]]
*[[Entactogens]]
*[[Entactogen]]
*[[Stimulants]]
*[[Stimulant]]
*[[Phenethylamines]]
*[[5-MAPB]]
*[[Amphetamines]]
*[[6-APB]]
*[[MDA]]
*[[MDA]]
*[[MDAI]]
*[[MDMA]]


==External links==
==External links==
*[http://drugs.tripsit.me/5-apb 5-APB (Tripsit)]
 
*[https://en.wikipedia.org/wiki/5-APB 5-APB (Wikipedia)]
*[https://en.wikipedia.org/wiki/5-APB 5-APB (Wikipedia)]
*[https://www.erowid.org/experiences/subs/exp_5APB.shtml 5-APB experiences (Erowid)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=2359 5-APB (Isomer Design)]
 
===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==
*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:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Amphetamine]]
[[Category:Research chemical]]
[[Category:Entactogen]]
[[Category:Stimulant]]
[[Category:Stimulant]]
[[Category:Substance]]
[[Category:Benzofuran]]
[[Category:Benzofuran]]
[[Category:Amphetamine]]
{{#set:Featured=true}}
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