|Systematic (IUPAC) name|
|Legal status||Class B (UK)|
|Mol. mass||175.23 g/mol|
|(what is this?)|
5-(2-aminopropyl)benzofuran or 1-benzofuran-5-ylpropan-2-amine (5-APB) is a triple monoamine reuptake inhibitor with Ki values of 180, 265 and 811 for NET, DAT and SERT respectively as well as being a potent agonist for the 5-HT2A and 5-HT2B receptors (Ki of 14nM at 5-HT2B). This 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. The subjective effects and structure-activity relationship suggest that 5-APB is also a monoamine releasing agent. Preliminary evidence suggests 5-APB is an inhibitor of the CYP2D6 enzyme.
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.
5-APB is also an agonist of the 5-HT2C receptor  as well as a triple monoamine reuptake inhibitor. It has been sold as a designer drug since 2010. Anecdotal reports from users suggest it has stimulant and empathogenic effects, but less psychedelic action than related compounds such as 6-APB and 5-APDB.
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.
Users describe effects as euphoric. Largely, effects reported were similar to that of the drug MDA but not as strong.
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.
- Dawson P, Opacka-Juffry J, Moffatt JD, Daniju Y, Dutta N, Ramsey J, Davidson C. The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat. Progress in Neuropsychopharmacology and Biological Psychiatry. 2014 Jan 3;48:57-63. doi: 10.1016/j.pnpbp.2013.08.013. PMID 24012617
- Iversen, L.; Gibbons, S.; Treble, R.; Setola, V.; Huang, X. P.; Roth, B. L. (2012). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. doi:10.1016/j.ejphar.2012.12.006.
- "Inhibition of CYP2D6 by 5-APB". Retrieved 19 November 2013.
- US patent 7045545, Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03
- EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
- "5-APB vs. 6-APB vs. MDMA".
- 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. Retrieved 2014-03-11.