5-APB

Use and effects

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. The drug has been reported to produce visual disturbances and is said to have mild psychedelic effects.

Recreational use of 5-APB has been associated with death in combination with other drugs and solely as the result of 5-APB.

Interactions

Pharmacology

Pharmacodynamics

5-APB acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with values for monoamine release of 19nM for serotonin, 21nM for norepinephrine, and 31nM for dopamine in rat brain synaptosomes. It is also a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).

5-APB is a potent agonist of the serotonin 5-HT2A and 5-HT2B receptors. Its () values were 6,300nM (54%) at the serotonin 5-HT2A receptor and 280nM (61–92%) at the serotonin 5-HT2B receptor. It also shows affinity for the serotonin 5-HT2C receptor (Ki = 880nM) and the serotonin 5-HT1A receptor (Ki = 3,300nM). 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. 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).

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.

Chemistry

5-APB, also known as 5-(2-aminopropyl)benzofuran, is a phenethylamine, amphetamine, and benzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).

Properties

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.

Synthesis

The chemical synthesis of 5-APB has been described.

Detection

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse. The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.

Analogues

Analogues of 5-APB include MDA, 5-APDB, 5-MAPB, 6-APB, 5-APBT, SDA (3T-MDA), and 5-API, among others.

History

5-APB, along with 6-APB, was first described in the scientific literature by Karin Briner and colleagues at Eli Lilly and Company in a patent in 2000. They were specifically studied as serotonin 5-HT2C receptor agonists for potential medical applications at this time. The description of 5-APB and 6-APB in the literature had followed the earlier work on 5-APDB and 6-APDB as serotonin releasing agents and entactogens by David E. Nichols and colleagues at Purdue University in 1993. 5-APB, along with 6-APB, emerged as a novel designer drug in 2010. 5-APB and 6-APB are often confused with 5-APDB and 6-APDB.

Society and culture

Legal status

Canada

5-APB may be a controlled substance in Canada under phenethylamine blanket-ban language.

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.

United States

5-APB is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

References

1. Anvisa. (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
2. (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol.
3. http://www.emcdda.europa.eu/publications/implementation-reports/2010 EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
4. Canal, Clinton E.. (2018). "New Psychoactive Substances". Springer International Publishing.
5. (August 20, 2014). "UCSD student dies of drug overdose after on-campus music festival". [[Los Angeles Times]].
6. (January 2014). "The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat". Progress in Neuro-Psychopharmacology & Biological Psychiatry.
7. (March 2015). "Acute 5-(2-aminopropyl)benzofuran (5-APB) intoxication and fatality: a case report with postmortem concentrations". Journal of Analytical Toxicology.
8. (July 2015). "Pharmacological profile of novel psychoactive benzofurans". British Journal of Pharmacology.
9. (January 2013). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology.
10. Greene, Shaun L. (2013). "Novel Psychoactive Substances". Elsevier.
11. "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists".
12. (November 2017). "Discriminative stimulus and locomotor effects of para-substituted and benzofuran analogs of amphetamine". Drug Alcohol Depend.
13. Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135 {{Webarchive. link. (2014-05-29)
14. USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf {{Webarchive. link. (2013-07-04)
15. (December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology (Berl).
16. "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists".
17. (August 2019). "Benzo fury: A new trend in the drug misuse scene". J Appl Toxicol.
18. (April 2020). "Designer drugs: mechanism of action and adverse effects". Arch Toxicol.
19. "Controlled Drugs and Substances Act".
20. UK Home Office. (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government.
21. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.