5-APB

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5-APB
5-APB2DACS.svg
Systematic (IUPAC) name
5-(2-Aminopropyl)benzofuran
Clinical data
Legal status Class B (UK)
Identifiers
CAS number 286834-80-8 N
ATC code None
PubChem CID 9837232
ChemSpider 8012953 YesY
Synonyms 1-Benzofuran-5-ylpropan-2-amine
Benzo fury
Benzofury
Chemical data
Formula C11H13NO 
Mol. mass 175.23 g/mol
 N (what is this?)  (verify)

5-APB (5-(2-aminopropyl)benzofuran, 1-benzofuran-5-ylpropan-2-amine, benzofury) is a triple monoamine reuptake inhibitor with Ki values of 180, 265 and 811 for NET, DAT and SERT respectively as well as being a potent agonist for the 5-HT2A and 5-HT2B receptors (Ki of 14nM at 5-HT2B).[1][2] 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. The subjective effects and structure-activity relationship suggest that 5-APB is also a monoamine releasing agent. Preliminary evidence suggests 5-APB is an inhibitor of the CYP2D6 enzyme.[3]

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 is also an agonist of the 5-HT2C receptor [4] as well as a triple monoamine reuptake inhibitor.[2] It has been sold as a designer drug since 2010.[5] Anecdotal reports from users suggest it has stimulant and empathogenic effects, but less psychedelic action than related compounds such as 6-APB and 5-APDB.[6]

Detection[edit]

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[7] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[8]

Effects[edit]

Users describe effects as euphoric. Largely, effects reported were similar to that of the drug MDA but not as strong.[citation needed] Recreational use of 5-APB has been associated with death in combination with other drugs.[9][10]

Legality[edit]

On March 5, 2014 the UK Home Office announced that 6-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.[11]

See also[edit]

References[edit]

  1. ^ Dawson P, Opacka-Juffry J, Moffatt JD, Daniju Y, Dutta N, Ramsey J, Davidson C. The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat. Progress in Neuropsychopharmacology and Biological Psychiatry. 2014 Jan 3;48:57-63. doi: 10.1016/j.pnpbp.2013.08.013. PMID 24012617 edit
  2. ^ a b Iversen, L.; Gibbons, S.; Treble, R.; Setola, V.; Huang, X. P.; Roth, B. L. (2012). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. doi:10.1016/j.ejphar.2012.12.006.  edit
  3. ^ "Inhibition of CYP2D6 by 5-APB". Retrieved 19 November 2013. 
  4. ^ US patent 7045545, Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03 
  5. ^ EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
  6. ^ "5-APB vs. 6-APB vs. MDMA". 
  7. ^ Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135
  8. ^ USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf
  9. ^ "UCSD student dies of drug overdose after on-campus music festival". Los Angeles Times. August 20, 2014. 
  10. ^ "The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat". Prog Neuropsychopharmacol Biol Psychiatry 48: 57–63. Jan 3, 2014. doi:10.1016/j.pnpbp.2013.08.013. PMID 24012617. "5-APB ... has been implicated in 10 recent drug-related deaths in the UK" 
  11. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.