5-APB: Difference between revisions

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'''5-(2-Aminopropyl)benzofuran''' (commonly known as '''5-APB''') is a lesser-known novel [[Psychoactive class::entactogen]] of the [[chemical class::benzofuran]] class that produces [[MDA]]-like [[entactogenic]] and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is structurally related to entactogens like [[5-MAPB]], [[6-APB]], and [[MDA]].

5-APB was first synthesized in 1993 by psychedelic chemist and researcher [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]].<ref name="Nichols">Monte, A. P., Marona-Lewicka, D., Cozzi, N. V., & Nichols, D. E. (1993). Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogs of 3, 4-(methylenedioxy) amphetamine. Journal of Medicinal Chemistry, 36(23), 3700-3706. https://doi.org/10.1021/jm00075a027</ref> However, 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. It was sold along with other novel benzofuran entactogens under the name "Benzofury" before its sale and import were subsequently banned.{{citation needed}}

Compared to other members of its family such as [[6-APB]] and [[5-MAPB]], this compound in particular is known for its [[stimulating]] and [[euphoria|euphoric]] effects which has resulted in its rise in popularity as a product which is easily accessible through the use of online [[research chemical]] vendors. It has been commercially distributed as a [[designer drug]] alternative to [[MDMA]] since 2010.<ref>EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA | http://www.emcdda.europa.eu/publications/implementation-reports/2010</ref>

Very little data exists about the pharmacological properties, metabolism, and toxicity of 5-APB in humans, and it has only a brief history of human usage. ~~Due to its potent entactogenic and stimulant effects, and dependence and addiction-producing potential if misused, it~~ is highly advised that one take proper precautions, conduct [https://www.google.com independent research], and use proper [[harm reduction practices]] if choosing to use with this substance.

Very little data exists about the pharmacological properties, metabolism, and toxicity of 5-APB in humans, and it has only a brief history of human usage. It is highly advised that one take proper precautions, conduct [https://www.google.com independent research], and use proper [[harm reduction practices]] if choosing to use with this substance.

==History and culture==

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==Chemistry==

5-(2-aminopropyl)benzofuran, also known as 5-APB, is a [[benzofuran]] and [[phenethylamine]], meaning it has an ethylamine chain and a furan ring attached to the core benzene ring. It can also be classified as an amphetamine derivative because the ethylamine chain is alpha methylated. Molecules of the amphetamine class contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα. The oxygen in the furan ring is placed at the 5 position, which generally constitutes more stimulating effects than when the oxygen is placed at the 6 position, which is usually described as being more [[psychedelic]] in effects. 5-APB is commonly found as the succinate and hydrochloride salt.{{citation needed}} The hydrochloride salt is 10% more potent by mass so doses should be adjusted accordingly.

==Pharmacology==

5-APB is a triple [[reuptake inhibitor]] for [[norepinephrine]], [[dopamine]] and [[serotonin]] as well as being an [[agonist]] for the [[Serotonin#The_5-HT_system|5-HT2A]] and [[Serotonin#The_5-HT_system|5-HT2B]] [[receptor]]s.<ref>The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/24012617?dopt=Abstract</ref><ref>Neurochemical profiles of some novel psychoactive substances (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299912010114</ref> It has also been speculated that 5-APB acts as a [[releasing agent]] for the previously mentioned [[neurotransmitters]].

@@ Line 3: / Line 3: @@
 '''5-(2-Aminopropyl)benzofuran''' (commonly known as '''5-APB''') is a lesser-known novel [[Psychoactive class::entactogen]] of the [[chemical class::benzofuran]] class that produces [[MDA]]-like [[entactogenic]] and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is structurally related to entactogens like [[5-MAPB]], [[6-APB]], and [[MDA]].
+-APB was first synthesized in 1993 by psychedelic chemist and researcher [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]].<ref name="Nichols">Monte, A. P., Marona-Lewicka, D., Cozzi, N. V., & Nichols, D. E. (1993). Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogs of 3, 4-(methylenedioxy) amphetamine. Journal of Medicinal Chemistry, 36(23), 3700-3706. https://doi.org/10.1021/jm00075a027</ref> However, 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. It was sold along with other novel benzofuran entactogens under the name "Benzofury" before its sale and import were subsequently banned.{{citation needed}}
 Compared to other members of its family such as [[6-APB]] and [[5-MAPB]], this compound in particular is known for its [[stimulating]] and [[euphoria|euphoric]] effects which has resulted in its rise in popularity as a product which is easily accessible through the use of online [[research chemical]] vendors. It has been commercially distributed as a [[designer drug]] alternative to [[MDMA]] since 2010.<ref>EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA | http://www.emcdda.europa.eu/publications/implementation-reports/2010</ref>
-Very little data exists about the pharmacological properties, metabolism, and toxicity of 5-APB in humans, and it has only a brief history of human usage. Due to its potent entactogenic and stimulant effects, and dependence and addiction-producing potential if misused, it is highly advised that one take proper precautions, conduct [https://www.google.com independent research], and use proper [[harm reduction practices]] if choosing to use with this substance.
+Very little data exists about the pharmacological properties, metabolism, and toxicity of 5-APB in humans, and it has only a brief history of human usage. It is highly advised that one take proper precautions, conduct [https://www.google.com independent research], and use proper [[harm reduction practices]] if choosing to use with this substance.
 ==History and culture==
@@ Line 17: / Line 19: @@
 ==Chemistry==
+{{chemistry}}
 -(2-aminopropyl)benzofuran, also known as 5-APB, is a [[benzofuran]] and [[phenethylamine]], meaning it has an ethylamine chain and a furan ring attached to the core benzene ring. It can also be classified as an amphetamine derivative because the ethylamine chain is alpha methylated. Molecules of the amphetamine class contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at R<sub>α</sub>. The oxygen in the furan ring is placed at the 5 position, which generally constitutes more stimulating effects than when the oxygen is placed at the 6 position, which is usually described as being more [[psychedelic]] in effects. 5-APB is commonly found as the succinate and hydrochloride salt.{{citation needed}} The hydrochloride salt is 10% more potent by mass so doses should be adjusted accordingly.
 ==Pharmacology==
+{{pharmacology}}
 -APB is a triple [[reuptake inhibitor]] for [[norepinephrine]], [[dopamine]] and [[serotonin]] as well as being an [[agonist]] for the [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] and [[Serotonin#The_5-HT_system|5-HT<sub>2B</sub>]] [[receptor]]s.<ref>The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/24012617?dopt=Abstract</ref><ref>Neurochemical profiles of some novel psychoactive substances (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299912010114</ref> It has also been speculated that 5-APB acts as a [[releasing agent]] for the previously mentioned [[neurotransmitters]].