6-APB

6-APB

Systematic (IUPAC) name
6-(2-aminopropyl)benzofuran
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	286834-85-3 N 286834-84-2 (hydrochloride)
ATC code	None
PubChem	CID 9794343
ChemSpider	7970110 Y
Chemical data
Formula	C11H13NO
Mol. mass	175.23 g/mol
SMILES NC(C)CC1=CC(OC=C2)=C2C=C1
InChI InChI=1S/C11H13NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3 Y Key:FQDAMYLMQQKPRX-UHFFFAOYSA-N Y
N (what is this?)  (verify)

6-(2-aminopropyl)benzofuran or 1-benzofuran-6-ylpropan-2-amine (6-APB) 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.

Pharmacology

6-APB is a triple monoamine reuptake inhibitor with K_i values of 117, 150 and 2698 for NET, DAT and SERT respectively as well as being a potent agonist for the 5-HT_2B receptor (K_i 3.7nM). The subjective effects and structure–activity relationship suggest that it is also a releasing agent.

The agonism for 5-HT_2B makes it likely that 6-APB would be cardiotoxic with long term use, as seen in other 5-HT_2B agonists such as fenfluramine and MDMA. 6-APB has also been claimed to act as an agonist of the 5-HT_2C 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-HT_2B 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-HT_2B receptors.

Law

6-APB is not listed under the Opium Law or the Medicine Act in the Netherlands, and thus currently legal.

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^{[citation needed]}, 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.^{[citation needed]} 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 10th 2013 6-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD reccomendation. This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.

6-APB is currently legal in Germany. If consumption is intended however, the German drug law takes effect automatically, prohibiting production and disposal.

6-APB is illegal in Sweden since the 4th of September, 2012, when it was added to the list of unhealthy substances.

See also

• MDA
• 6-MAPB
• 5-APB
• 5-APDB
• 6-APDB
• 5-(2-Aminopropyl)indole
• Ethylenedioxymethamphetamine
• Indanylaminopropane
• Naphthylaminopropane
• Tetralinylaminopropane