5-APB

5-APB (abbreviation of "5-(2-aminopropyl)benzofuran"; see infobox for the correct IUPAC name) is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 5-APB and other compounds are sometimes informally called "Benzofury".

5-APB
Clinical data
Other names1-Benzofuran-5-ylpropan-2-amine
ATC code
  • none
Legal status
Legal status
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 is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass and doses should be adjusted accordingly.

5-APB has been sold as a designer drug since 2010.[1]

Pharmacology

5-APB is a serotonin–norepinephrine–dopamine reuptake inhibitor with Ki(NET)=180 nmol/L, Ki(DAT)=265 nmol/L and Ki(SERT)=811 nmol/L.[2] It is also a serotonin–norepinephrine–dopamine releasing agent.[3] 5-APB is a potent agonist for the 5-HT2A and 5-HT2B receptors (Ki of 14 nmol/L at 5-HT2B with an efficacy of[2] 0.924). This agonism for 5-HT2B makes it likely that 5-APB would be cardiotoxic with long term use, as seen in other 5-HT2B agonists such as fenfluramine and MDMA. 5-APB is also an agonist of the 5-HT2C receptor.[4]

Detection

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[5] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[6]

Effects

Users describe effects as euphoric. Largely, effects reported were similar to that of the drug MDMA but not as strong. Recreational use of 5-APB has been associated with death in combination with other drugs[7][8] and solely as the result of 5-APB.[9]

According to investigative reporting by David Nickles and Lily Kay Ross, a coroner's report identified "complications of 5-APB and other substance abuse" as the cause of death of Jen Rothman, who had been introduced to 5-APB by psychedelic practitioner Jorge Ferrer. The reporters state that the mechanism of death was likely to have been hyponatremia, caused by the increased action of serotonin induced by 5-APB. They note that telltale symptoms of hyponatremia, "Thirst, exhaustion, seizures, and vomiting [were] in Jen’s texts and the police report" pertaining to the incident.[10] Such an effect has been documented for MDMA, which has a similar mechanism of action and subjective effects.[11]

Legality

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.[12]

References
  1. http://www.emcdda.europa.eu/publications/implementation-reports/2010 EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
  2. 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): 147–51. doi:10.1016/j.ejphar.2012.12.006. PMC 3582025. PMID 23261499.
  3. 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.
  4. US patent 7045545, Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03
  5. Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135 Archived 2014-05-29 at the Wayback Machine
  6. USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf
  7. "UCSD student dies of drug overdose after on-campus music festival". Los Angeles Times. August 20, 2014.
  8. 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
  9. 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.
  10. David Nickles and Lily Kay Ross (15 March 2022). "Cover Story, Season 1, Episode 8: Who Am I Fooling" (Podcast). New York Magazine and Psymposia. Retrieved 15 March 2022.
  11. van Dijken GD, Blom RE, Hené RJ, Boer WH (September 2013). "High incidence of mild hyponatraemia in females using ecstasy at a rave party". Nephrology Dialysis Transplantation. 28 (9): 2277–2283. doi:10.1093/ndt/gft023.
  12. UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
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