|Systematic (IUPAC) name|
|Mol. mass||175.23 g/mol|
| (what is this?)
6-(2-aminopropyl)benzofuran or 1-benzofuran-6-ylpropan-2-amine (6-APB), also known as Benzofury is an entactogenic compound of the phenethylamine and amphetamine classes. It is similar in structure to MDA but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB.
6-APB is a triple monoamine reuptake inhibitor with Ki values of 117, 150 and 2698 for NET, DAT and SERT respectively as well as being a potent agonist for the 5-HT2B receptor (Ki 3.7nM). The subjective effects and structure–activity relationship suggest that it is also a releasing agent.
The agonism for 5-HT2B makes it likely that 6-APB would be cardiotoxic with long term use, as seen in other 5-HT2B agonists such as fenfluramine and MDMA. 6-APB has also been claimed to act as an agonist of the 5-HT2C receptor and therefore be useful as an appetite suppressant. However while 6-APB is an agonist at all three 5-HT2 receptor subtypes, its potency at 5-HT2B is significantly higher, and it is actually both more potent and more selective over other serotonin receptors than the reference agonist BW723C86 which is commonly used for research into 5-HT2B receptors.
6-APB is unscheduled in the United States, but not currently approved by the Food and Drug Administration for human consumption.
Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APB as it is in some respects similar in chemical structure to the class A drug MDA, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.
6-APB is unscheduled under the Controlled Drugs and Substances Act (CDSA) in Canada, although there is a Schedule III amphetamine analogue clause. Due to 6-APB's structure, it may be considered an analogue of MDA, but these types of offenses are rarely prosecuted. Canada's CDSA defines an analogue as any substance that, in relation to a controlled substance, has a substantially similar chemical structure.
6-APB is unscheduled in France and Italy.
On June 10, 2013 6-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation. This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.
6-APB is illegal in Germany since the 17th of July, 2013, when it was added to the Betäubungsmittelgesetz.
In Sweden, 6-APB is classified as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of December 27, 2009 under SFS 2009:1095 making it illegal to sell or possess.
- 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.
- US patent 7045545, Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03
- "Misuse of Drugs Act 1975 New Zealand.". legislation.govt.nz. Archived from the original on 28 July 2010. Retrieved 2010-08-06.
- "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 04 Jun 2013. Retrieved 2013-06-13.
- "'NBOMe' and 'Benzofury' banned". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13.
- Verordnung zur Änderung von betäubungsmittelrechtlichen Vorschriften, Art. 1 VO vom 9. Juli 2013(BGBl. I S. 2274)