6-APDB: Difference between revisions

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6-APDB was first synthesized and studied along with [[5-APDB]] in 1993 by [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]]<ref> "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine"|https://www.ncbi.nlm.nih.gov/pubmed/8246240</ref>. It did not come into popular recreational use until over a decade later, where it briefly entered the rave scene and global research chemicals market, in particular the "legal highs" market in the U.K., before its sale and import were subsequently banned.

Because 6-APDB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity as a substitute or replacement for serotonergic [[entactogens]] like MDMA or MDA, and are typically distributed through the online research chemicals grey market.

Because 6-APDB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity as a substitute or replacement for serotonergic entactogens like MDMA or MDA, and are typically distributed through the online research chemicals grey market.

==Chemistry==

[[File:Phenethylamine.png|thumb|right|253px|thumb|right|253px||General formula of a phenethylamine molecule]]

6-APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran, is a synthetic molecule of the [[benzofuran]] family. Molecules of this class contain a [[phenethylamine]] core bound to an amino (~~NH2~~) group through an ethyl chain with an additional methyl substitution at Rα.

6-APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran, is a synthetic molecule of the [[benzofuran]] family. Molecules of this class contain a [[phenethylamine]] core bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα.

6-APDB does not contain a methyl substitution on RN, a motif which it shares with [[MDA]]. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene bridge. 6-APDB shares this furan ring with 5-APDB, 5-MAPDB and 6-MAPDB.

6-APDB does not contain a methyl substitution on RN, a motif which it shares with [[MDA]]. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene bridge. 6-APDB shares this furan ring with [[5-APDB]], [[5-MAPDB]] and [[6-MAPDB]].

==Pharmacology==

6-APDB acts as a [[releasing agent]] and triple [[reuptake inhibitor]] of the monoamine [[neurotransmitters]] known as [[serotonin]], [[dopamine]] and [[noradrenaline]]<ref>Effects of 6-APDB on the release of monoamines from rat brain slices https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3582025/</ref> which are the global [[neurotransmitters]] that modulate the brain's ability to feel pleasure, motivation, reward, planning, attention and focus. This is done by promoting the release and inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse through release into the synaptic cleft, essentially allowing them to accumulate and render them liable for immediate reuse. The net result is excitation in a manner which causes a combination of physically stimulating, relaxing, disinhibiting and euphoric effects.<ref>New Insights into the Mechanism of Action of Amphetamines | http://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.47.120505.105140</ref>

The unsaturated benzofuran derivative [[6-APB]], or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB has yet to be fully elucidated.

The unsaturated benzofuran derivative [[6-APB]], or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between [[6-APB]] and 6-APDB has yet to be fully elucidated.

==Subjective effects==

@@ Line 10: / Line 10: @@
 -APDB was first synthesized and studied along with [[5-APDB]] in 1993 by [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]]<ref> "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine"|https://www.ncbi.nlm.nih.gov/pubmed/8246240</ref>. It did not come into popular recreational use until over a decade later, where it briefly entered the rave scene and global research chemicals market, in particular the "legal highs" market in the U.K., before its sale and import were subsequently banned.
-Because 6-APDB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity as a substitute or replacement for serotonergic [[entactogens]] like MDMA or MDA, and are typically distributed through the online research chemicals grey market.
+Because 6-APDB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity as a substitute or replacement for serotonergic entactogens like MDMA or MDA, and are typically distributed through the online research chemicals grey market.
 ==Chemistry==
 [[File:Phenethylamine.png|thumb|right|253px|thumb|right|253px||General formula of a phenethylamine molecule]]
--APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran, is a synthetic molecule of the [[benzofuran]] family.  Molecules of this class contain a [[phenethylamine]] core bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>.
+-APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran, is a synthetic molecule of the [[benzofuran]] family.  Molecules of this class contain a [[phenethylamine]] core bound to an amino (NH<sub>2</sub>) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>.
--APDB does not contain a methyl substitution on R<sub>N</sub>, a motif which it shares with [[MDA]]. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene bridge. 6-APDB shares this furan ring with 5-APDB, 5-MAPDB and 6-MAPDB.
+-APDB does not contain a methyl substitution on R<sub>N</sub>, a motif which it shares with [[MDA]]. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene bridge. 6-APDB shares this furan ring with [[5-APDB]], [[5-MAPDB]] and [[6-MAPDB]].
 ==Pharmacology==
 -APDB acts as a [[releasing agent]] and triple [[reuptake inhibitor]] of the monoamine [[neurotransmitters]] known as [[serotonin]], [[dopamine]] and [[noradrenaline]]<ref>Effects of 6-APDB on the release of monoamines from rat brain slices https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3582025/</ref> which are the global [[neurotransmitters]] that modulate the brain's ability to feel pleasure, motivation, reward, planning, attention and focus. This is done by promoting the release and inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse through release into the synaptic cleft, essentially allowing them to accumulate and render them liable for immediate reuse. The net result is excitation in a manner which causes a combination of physically stimulating, relaxing, disinhibiting and euphoric effects.<ref>New Insights into the Mechanism of Action of Amphetamines | http://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.47.120505.105140</ref>
-The unsaturated benzofuran derivative [[6-APB]], or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB has yet to be fully elucidated.
+The unsaturated benzofuran derivative [[6-APB]], or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between [[6-APB]] and 6-APDB has yet to be fully elucidated.
 ==Subjective effects==