5-APB
Entactogen
From Wikipedia, the free encyclopedia
5-APB, also known as 5-(2-aminopropyl)benzofuran, is an entactogen of the phenethylamine, amphetamine, and benzofuran families.[1] 5-APB and related drugs have sometimes been informally called "Benzofury".
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| Other names | 1-Benzofuran-5-ylpropan-2-amine |
| Routes of administration | Oral[1] |
| Drug class | Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Stimulant; Psychedelic |
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| Duration of action | 3–8 hours[1] |
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| Formula | C11H13NO |
| Molar mass | 175.231 g·mol−1 |
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5-APB was first described in the scientific literature in 2000[3][4][5][6] and emerged as a novel designer drug in 2010.[4][5][7][8]
Use and effects
Users describe the effects of 5-APB as including euphoria among others.[4] Largely, its effects reported were similar to those of the drug MDMA but not as strong.[citation needed] The drug has been reported to produce visual disturbances and is said to have mild psychedelic effects.[4][9]
Recreational use of 5-APB has been associated with death in combination with other drugs[10][11] and solely as the result of 5-APB.[12]
Interactions
Pharmacology
Pharmacodynamics
5-APB acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 values for monoamine release of 19 nM for serotonin, 21 nM for norepinephrine, and 31 nM for dopamine in rat brain synaptosomes.[7][13] It is also a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).[7]
5-APB is a potent agonist of the serotonin 5-HT2A and 5-HT2B receptors.[7][13] Its EC50 (Emax) values were 6,300 nM (54%) at the serotonin 5-HT2A receptor and 280 nM (61–92%) at the serotonin 5-HT2B receptor.[7][13] It also shows affinity for the serotonin 5-HT2C receptor (Ki = 880 nM) and the serotonin 5-HT1A receptor (Ki = 3,300 nM).[7][13] It has been reported to act as an agonist of the serotonin 5-HT2C receptor similarly to the serotonin 5-HT2A and 5-HT2B receptors.[4][14] The drug's potent agonism of the serotonin 5-HT2B receptor makes it likely that 5-APB would be cardiotoxic with long-term use, as seen with other serotonin 5-HT2B receptor agonists such as fenfluramine and MDMA.[citation needed]
5-APB also shows high affinity for the mouse and rat trace amine-associated receptor 1 (TAAR1).[7]
In animal studies, 5-APB produces robust hyperlocomotion, robust conditioned place preference (CPP) but limited self-administration, fully substitutes for MDMA in drug discrimination tests, and partially substitutes for DOM, cocaine, and methamphetamine in drug discrimination tests.[15]
Chemistry
5-APB, also known as 5-(2-aminopropyl)benzofuran, is a phenethylamine, amphetamine, and benzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).
Properties
5-APB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass and doses should be adjusted accordingly.
Synthesis
The chemical synthesis of 5-APB has been described.[6]
Detection
A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[16] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[17]
Analogues
Analogues of 5-APB include MDA, 5-APDB, 5-MAPB, 6-APB, 5-APBT, SDA (3T-MDA), and 5-API, among others.
History
5-APB, along with 6-APB, was first described in the scientific literature by Karin Briner and colleagues at Eli Lilly and Company in a patent in 2000.[3][4][5][6] They were specifically studied as serotonin 5-HT2C receptor agonists for potential medical applications at this time.[3][4][5][6] The description of 5-APB and 6-APB in the literature had followed the earlier work on 5-APDB and 6-APDB as serotonin releasing agents and entactogens by David E. Nichols and colleagues at Purdue University in 1993.[5][7][18] 5-APB, along with 6-APB, emerged as a novel designer drug in 2010.[4][5][7][8] 5-APB and 6-APB are often confused with 5-APDB and 6-APDB.[5]
Society and culture
Legal status
Canada
5-APB may be a controlled substance in Canada under phenethylamine blanket-ban language.[19]
United Kingdom
On March 5, 2014 the UK Home Office announced that 5-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.[20]
United States
5-APB is not an explicitly controlled substance in the United States.[21] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.