Chemistry:5-APB
5-APB (abbreviation of "5-(2-aminopropyl)benzofuran") is an empathogenic psychoactive compound of the phenethylamine, amphetamine, and benzofuran families. The drug and other compounds have sometimes been informally called "Benzofury". 5-APB has been sold as a designer drug since 2010.[1]
Effects
Users describe the effects of 5-APB as including euphoria among others.[2] Largely, its effects reported were similar to those of the drug MDMA but not as strong. The drug has been reported to produce visual disturbances and is said to have mild psychedelic effects.[2][3]
Recreational use of 5-APB has been associated with death in combination with other drugs[4][5] and solely as the result of 5-APB.[6]
Pharmacology
5-APB acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 values for monoamine release of 19 nM for serotonin, 21 nM for norepinephrine, and 31 nM for dopamine in rat brain synaptosomes.[7][8] It is also a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).[7]
5-APB is a potent agonist of the serotonin 5-HT2A and 5-HT2B receptors.[7][8] Its EC50 (Emax) values were 6,300 nM (54%) at the serotonin 5-HT2A receptor and 280 nM (61–92%) at the serotonin 5-HT2B receptor.[7][8] It also shows affinity for the serotonin 5-HT2C receptor (Ki = 880 nM) and the serotonin 5-HT1A receptor (Ki = 3,300 nM).[7][8] It has been reported to act as an agonist of the serotonin 5-HT2C receptor similarly to the serotonin 5-HT2A and 5-HT2B receptors.[2][9] The drug's potent agonism of the serotonin 5-HT2B receptor makes it likely that 5-APB would be cardiotoxic with long-term use, as seen with other serotonin 5-HT2B receptor agonists such as fenfluramine and MDMA. 5-APB also shows high affinity for the mouse and rat trace amine-associated receptor 1 (TAAR1).[7]
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.[10]
Chemistry
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.
Detection
A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[11] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[12]
Society and culture
Legal status
United Kingdom
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.[13]
See also
References
- ↑ http://www.emcdda.europa.eu/publications/implementation-reports/2010 EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
- ↑ 2.0 2.1 2.2 Greene, Shaun L (2013). "Benzofurans and Benzodifurans". Novel Psychoactive Substances. Elsevier. pp. 383–392. doi:10.1016/b978-0-12-415816-0.00016-x. ISBN 978-0-12-415816-0. https://linkinghub.elsevier.com/retrieve/pii/B978012415816000016X. Retrieved 15 April 2025.
- ↑ Canal, Clinton E. (2018). "Serotonergic Psychedelics: Experimental Approaches for Assessing Mechanisms of Action". New Psychoactive Substances. Handbook of Experimental Pharmacology. 252. Cham: Springer International Publishing. pp. 227–260. doi:10.1007/164_2018_107. ISBN 978-3-030-10560-0. "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."
- ↑ "UCSD student dies of drug overdose after on-campus music festival". Los Angeles Times. August 20, 2014. http://www.latimes.com/local/lanow/la-me-ln-ucsd-student-drug-overdose-20140820-story.html.
- ↑ "The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat". Progress in Neuro-Psychopharmacology & Biological Psychiatry 48: 57–63. January 2014. doi:10.1016/j.pnpbp.2013.08.013. PMID 24012617. http://clok.uclan.ac.uk/18222/1/5APB%20in%20press.pdf. "5-APB ... has been implicated in 10 recent drug-related deaths in the UK".
- ↑ "Acute 5-(2-aminopropyl)benzofuran (5-APB) intoxication and fatality: a case report with postmortem concentrations". Journal of Analytical Toxicology 39 (2): 156–9. March 2015. doi:10.1093/jat/bku131. PMID 25429871.
- ↑ 7.0 7.1 7.2 7.3 7.4 7.5 "Pharmacological profile of novel psychoactive benzofurans". British Journal of Pharmacology 172 (13): 3412–25. July 2015. doi:10.1111/bph.13128. PMID 25765500.
- ↑ 8.0 8.1 8.2 8.3 "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology 700 (1–3): 147–151. January 2013. doi:10.1016/j.ejphar.2012.12.006. PMID 23261499.
- ↑ Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", US patent 7045545, published 2000-01-19, issued 2006-16-03
- ↑ "Discriminative stimulus and locomotor effects of para-substituted and benzofuran analogs of amphetamine". Drug Alcohol Depend 180: 39–45. November 2017. doi:10.1016/j.drugalcdep.2017.07.041. PMID 28865391.
- ↑ Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135
- ↑ USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf
- ↑ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. http://www.legislation.gov.uk/ukdsi/2014/9780111110904.
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