5-APB

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5-APB
5-APB2DACS.svg
Ball-and-stick model of the 5-APB molecule
Clinical data
Synonyms 1-Benzofuran-5-ylpropan-2-amine
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.230.221
Chemical and physical data
Formula C11H13NO
Molar mass 175.23 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

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 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[edit]

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.[citation needed] 5-APB is also an agonist of the 5-HT2C receptor.[4]

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.[5] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[6]

Effects[edit]

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

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.[9]

References[edit]

  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. ^ a b Iversen, L.; Gibbons, S.; Treble, R.; Setola, V.; Huang, X. P.; Roth, B. L. (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 3582025Freely accessible. PMID 23261499. 
  3. ^ Rickli, A; Kopf, S; Hoener, MC; Liechti, ME (2015). "Pharmacological profile of novel psychoactive benzofurans". British Pharmacological Society. 172 (13): 3412–25. doi:10.1111/bph.13128. PMC 4500375Freely accessible. 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
  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, J. D; Daniju, Y; Dutta, N; Ramsey, J; Davidson, C (Jan 3, 2014). "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. doi:10.1016/j.pnpbp.2013.08.013. PMID 24012617. 5-APB ... has been implicated in 10 recent drug-related deaths in the UK 
  9. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.