6-APB (6-(2-aminopropyl)benzofuran) is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes.
6-APB and other compounds are sometimes informally called “Benzofury” in newspaper reports. 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. It may appear as a tan grainy powder.
Although limited literature is available, there is some data on metabolism of 6-APB in rats. Its Phase I metabolism involves hydroxylation of the furan ring, then cleavage of the ring, followed by a reduction of the unsaturated aldehyde from the previous step. The resulting aldehyde may then take two paths. It is either oxidized to a carboxylic acid or reduced to an alcohol, and then hydroxylated. Phase II metabolism consists of glucuronidation. The most prevalent metabolites in rats were 3-carboxymethyl-4-hydroxyamphetamine and 4-carboxymethyl-3-hydroxyamphetamine.
The synthesis by Briner et al. entailed refluxing 3-bromophenol with bromoacetaldehyde and sodium hydride to give the diethyl acetal, which then was heated with polyphosphoric acid to give a mixture of bromobenzofuran structural isomers: 4-bromo-1-benzofuran and 6-bromo-1-benzofuran. The isomers were separated by silica gel column chromatography, then converted to their respective propanone derivatives, and then reductively aminated to give 6-APB and 4-APB, both of which were converted to their HCl ion pairs for further examination.
The pharmacokinetics of 6-APB have not been studied, however, some information can be extracted from user reports. These suggest a slow onset of 40–120 minutes. The drugs peak effects last 7 hours, followed by a comedown phase of approximately 2 hours, and after effects for up to 24 hours.
Formal Name :α-methyl-6-benzofuranethanamine, monohydrochloride
CAS Number :286834-84-2
Synonyms :6-(2-Aminopropyl)Benzofuran Benzo Fury
Molecular Formula :C11H13NO • HCl
Formula Weight :211.7
Formulation :A crystalline solid
λmax :207, 246, 276, 285 nm
InChI Code :InChI=1S/C11H13NO.ClH/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9;/h2-5,7-8H,6,12H2,1H3;1H
InChI Key :APEWOTOLPKNSPE-UHFFFAOYSA-N