5-APB

Users describe the effects of 5-APB as including euphoria among others. Largely, its effects reported were similar to those of the drug MDMA but not as strong.{{citation needed|date=February 2014}} The drug has been reported to produce visual disturbances and is said to have mild psychedelic effects.{{cite book | last=Canal | first=Clinton E. | title=New Psychoactive Substances | chapter=Serotonergic Psychedelics: Experimental Approaches for Assessing Mechanisms of Action | publisher=Springer International Publishing | publication-place=Cham | volume=252 | date=2018 | isbn=978-3-030-10560-0 | pmid=29532180 | pmc=6136989 | doi=10.1007/164_2018_107 | doi-access=free | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6136989 | access-date=15 April 2025 | page=227–260 | quote=Despite micromolar 5-HT1A affinities (Rickli et al. 2015b), Nbenzylphenethylamines retain potent psychedelic effects. Also, benzofurans, such as 5-APB and 6-APB, are potent and efficacious 5-HT2B agonists but have very low potency at 5-HT2A receptors. They also stimulate efflux of DA and 5-HT and have activity at TAAR1 receptors (Iversen et al. 2013; Rickli et al. 2015a), but anecdotal reports note that psychedelic effects are relatively minor compared to classic psychedelics. These observations provide further credence that the 5-HT2A receptor, but not 5-HT1A, 5-HT2B, TAAR1, or monoamine transporters, initiates psychedelic effects.}}

Recreational use of 5-APB has been associated with death in combination with other drugs{{cite news | url = http://www.latimes.com/local/lanow/la-me-ln-ucsd-student-drug-overdose-20140820-story.html | title = UCSD student dies of drug overdose after on-campus music festival | newspaper = Los Angeles Times | date = August 20, 2014}}{{cite journal | vauthors = Dawson P, Opacka-Juffry J, Moffatt JD, Daniju Y, Dutta N, Ramsey J, Davidson C | title = The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 48 | pages = 57–63 | date = January 2014 | pmid = 24012617 | doi = 10.1016/j.pnpbp.2013.08.013 | s2cid = 23400101 | url = http://clok.uclan.ac.uk/18222/1/5APB%20in%20press.pdf | quote = 5-APB ... has been implicated in 10 recent drug-related deaths in the UK }} and solely as the result of 5-APB.{{cite journal | vauthors = McIntyre IM, Gary RD, Trochta A, Stolberg S, Stabley R | title = Acute 5-(2-aminopropyl)benzofuran (5-APB) intoxication and fatality: a case report with postmortem concentrations | journal = Journal of Analytical Toxicology | volume = 39 | issue = 2 | pages = 156–9 | date = March 2015 | pmid = 25429871 | doi = 10.1093/jat/bku131 | doi-access = free }}

5-APB acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with {{Abbrlink|EC₅₀|half-maximal effective concentration}} values for monoamine release of 19{{nbsp}}nM for serotonin, 21{{nbsp}}nM for norepinephrine, and 31{{nbsp}}nM for dopamine in rat brain synaptosomes.{{cite journal | vauthors = Rickli A, Kopf S, Hoener MC, Liechti ME | title = Pharmacological profile of novel psychoactive benzofurans | journal = British Journal of Pharmacology | volume = 172 | issue = 13 | pages = 3412–25 | date = July 2015 | pmid = 25765500 | pmc = 4500375 | doi = 10.1111/bph.13128 }}{{cite journal | vauthors = Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL |author6-link=Bryan Roth | title = Neurochemical profiles of some novel psychoactive substances | journal = European Journal of Pharmacology | volume = 700 | issue = 1–3 | pages = 147–151 | date = January 2013 | pmid = 23261499 | pmc = 3582025 | doi = 10.1016/j.ejphar.2012.12.006 }} It is also a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).

5-APB is a potent agonist of the serotonin 5-HT_2A and 5-HT_2B receptors. Its {{Abbrlink|EC₅₀|half-maximal effective concentration}} ({{Abbrlink|E_max|maximal efficacy}}) values were 6,300{{nbsp}}nM (54%) at the serotonin 5-HT_2A receptor and 280{{nbsp}}nM (61–92%) at the serotonin 5-HT_2B receptor. It also shows affinity for the serotonin 5-HT_2C receptor (K_i = 880{{nbsp}}nM) and the serotonin 5-HT_1A receptor (K_i = 3,300{{nbsp}}nM). It has been reported to act as an agonist of the serotonin 5-HT_2C receptor similarly to the serotonin 5-HT_2A and 5-HT_2B receptors.{{cite book | last=Greene | first=Shaun L | title=Novel Psychoactive Substances | chapter=Benzofurans and Benzodifurans | publisher=Elsevier | date=2013 | isbn=978-0-12-415816-0 | doi=10.1016/b978-0-12-415816-0.00016-x | url=https://linkinghub.elsevier.com/retrieve/pii/B978012415816000016X | access-date=15 April 2025 | page=383–392}}{{ cite patent | country = US | number = 7045545 | status = patent | title = Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists | pubdate = 2000-01-19 | gdate = 2006-16-03 | inventor = Karin Briner et al | url = https://patents.google.com/patent/US7045545B1/}} The drug's potent agonism of the serotonin 5-HT_2B receptor makes it likely that 5-APB would be cardiotoxic with long-term use, as seen with other serotonin 5-HT_2B receptor agonists such as fenfluramine and MDMA.{{Citation needed|date=September 2017}}

5-APB also shows high affinity for the mouse and rat trace amine-associated receptor 1 (TAAR1).

In animal studies, 5-APB produces robust hyperlocomotion, robust conditioned place preference (CPP) but limited self-administration, fully substitutes for MDMA in drug discrimination tests, and partially substitutes for DOM, cocaine, and methamphetamine in drug discrimination tests.{{cite journal | vauthors = Dolan SB, Forster MJ, Gatch MB | title = Discriminative stimulus and locomotor effects of para-substituted and benzofuran analogs of amphetamine | journal = Drug Alcohol Depend | volume = 180 | issue = | pages = 39–45 | date = November 2017 | pmid = 28865391 | pmc = 6463889 | doi = 10.1016/j.drugalcdep.2017.07.041 | url = https://pmc.ncbi.nlm.nih.gov/articles/PMC6463889/pdf/nihms-1016834.pdf}}

5-APB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass and doses should be adjusted accordingly.

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135 {{Webarchive|url=https://web.archive.org/web/20140529051608/http://forendex.southernforensic.org/index.php/detail/index/1135 |date=2014-05-29 }} The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf

On March 5, 2014 the UK Home Office announced that 5-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.{{cite web | url = http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | title = The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | access-date = 2014-03-11 | author = UK Home Office | date = 2014-03-05 | publisher = UK Government}}

• Borax combo
• 6-APB
• 5-APBT
• 5-API
• 5-APDB

{{Reflist}}

{{Entactogens}}

{{Psychedelics}}

{{Monoamine releasing agents}}

{{Serotonin receptor modulators}}

{{TAAR modulators}}

{{Phenethylamines}}

{{Chemical classes of psychoactive drugs}}

Category:5-HT2A agonists

Category:5-HT2B agonists

Category:5-HT2C agonists

Category:5-Benzofuranethanamines

Category:Designer drugs

Category:Entactogens

Category:Psychedelic phenethylamines

Category:Serotonin-norepinephrine-dopamine releasing agents

Category:Serotonin receptor agonists

Category:Stimulants

Category:Substituted amphetamines

Category:TAAR1 modulators