5-APB

5-APB
Clinical data
Other names1-Benzofuran-5-ylpropan-2-amine
Routes of
administration		Oral
Drug classSerotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Stimulant; Psychedelic
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F2 (Prohibited psychotropics)[1]
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • UN: Unscheduled.
Identifiers
  • 1-(1-benzofuran-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13NO
Molar mass175.231 g·mol−1
3D model (JSmol)
  • CC(N)CC1=CC(C=CO2)=C2C=C1
  • InChI=1S/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3 Y
  • Key:VKUMKUZDZWHMQU-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

5-APB (abbreviation of "5-(2-aminopropyl)benzofuran") is an empathogenic psychoactive compound of the phenethylamine, amphetamine, and benzofuran families. The drug and other compounds have sometimes been informally called "Benzofury". 5-APB has been sold as a designer drug since 2010.[2]

Effects

Users describe the effects of 5-APB as including euphoria among others.[3] Largely, its effects reported were similar to those of the drug MDMA but not as strong. The drug has been reported to produce visual disturbances and is said to have mild psychedelic effects.[3][4]

Recreational use of 5-APB has been associated with death in combination with other drugs[5][6] and solely as the result of 5-APB.[7]

Pharmacology

5-APB acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50Tooltip half-maximal effective concentration values for monoamine release of 19 nM for serotonin, 21 nM for norepinephrine, and 31 nM for dopamine in rat brain synaptosomes.[8][9] It is also a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).[8]

5-APB is a potent agonist of the serotonin 5-HT2A and 5-HT2B receptors.[8][9] Its EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values were 6,300 nM (54%) at the serotonin 5-HT2A receptor and 280 nM (61–92%) at the serotonin 5-HT2B receptor.[8][9] It also shows affinity for the serotonin 5-HT2C receptor (Ki = 880 nM) and the serotonin 5-HT1A receptor (Ki = 3,300 nM).[8][9] 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.[3][10] 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.

5-APB also shows high affinity for the mouse and rat trace amine-associated receptor 1 (TAAR1).[8]

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.[11]

Chemistry

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.

Detection

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[12] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[13]

Society and culture

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.[14]

See also

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ http://www.emcdda.europa.eu/publications/implementation-reports/2010 EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
  3. ^ a b c Greene, Shaun L (2013). "Benzofurans and Benzodifurans". Novel Psychoactive Substances. Elsevier. p. 383–392. doi:10.1016/b978-0-12-415816-0.00016-x. ISBN 978-0-12-415816-0. Retrieved 15 April 2025.
  4. ^ Canal, Clinton E. (2018). "Serotonergic Psychedelics: Experimental Approaches for Assessing Mechanisms of Action". New Psychoactive Substances. Vol. 252. Cham: Springer International Publishing. p. 227–260. doi:10.1007/164_2018_107. ISBN 978-3-030-10560-0. PMC 6136989. PMID 29532180. Retrieved 15 April 2025. Despite micromolar 5-HT1A affinities (Rickli et al. 2015b), Nbenzylphenethylamines retain potent psychedelic effects. Also, benzofurans, such as 5-APB and 6-APB, are potent and efficacious 5-HT2B agonists but have very low potency at 5-HT2A receptors. They also stimulate efflux of DA and 5-HT and have activity at TAAR1 receptors (Iversen et al. 2013; Rickli et al. 2015a), but anecdotal reports note that psychedelic effects are relatively minor compared to classic psychedelics. These observations provide further credence that the 5-HT2A receptor, but not 5-HT1A, 5-HT2B, TAAR1, or monoamine transporters, initiates psychedelic effects.
  5. ^ "UCSD student dies of drug overdose after on-campus music festival". Los Angeles Times. August 20, 2014.
  6. ^ Dawson P, Opacka-Juffry J, Moffatt JD, Daniju Y, Dutta N, Ramsey J, Davidson C (January 2014). "The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat" (PDF). Progress in Neuro-Psychopharmacology & Biological Psychiatry. 48: 57–63. doi:10.1016/j.pnpbp.2013.08.013. PMID 24012617. S2CID 23400101. 5-APB ... has been implicated in 10 recent drug-related deaths in the UK
  7. ^ McIntyre IM, Gary RD, Trochta A, Stolberg S, Stabley R (March 2015). "Acute 5-(2-aminopropyl)benzofuran (5-APB) intoxication and fatality: a case report with postmortem concentrations". Journal of Analytical Toxicology. 39 (2): 156–9. doi:10.1093/jat/bku131. PMID 25429871.
  8. ^ a b c d e f Rickli A, Kopf S, Hoener MC, Liechti ME (July 2015). "Pharmacological profile of novel psychoactive benzofurans". British Journal of Pharmacology. 172 (13): 3412–25. doi:10.1111/bph.13128. PMC 4500375. PMID 25765500.
  9. ^ a b c d Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (January 2013). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. 700 (1–3): 147–151. doi:10.1016/j.ejphar.2012.12.006. PMC 3582025. PMID 23261499.
  10. ^ US patent 7045545, Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03 
  11. ^ Dolan SB, Forster MJ, Gatch MB (November 2017). "Discriminative stimulus and locomotor effects of para-substituted and benzofuran analogs of amphetamine" (PDF). Drug Alcohol Depend. 180: 39–45. doi:10.1016/j.drugalcdep.2017.07.041. PMC 6463889. PMID 28865391.
  12. ^ Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135 Archived 2014-05-29 at the Wayback Machine
  13. ^ USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf
  14. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.