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 names	1-Benzofuran-5-ylpropan-2-amine
ATC code	none
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B
Identifiers
IUPAC name 1-(1-benzofuran-5-yl)propan-2-amine
CAS Number	286834-81-9 Y
PubChem CID	9837232
ChemSpider	8012953 Y
UNII	2M3825704H
CompTox Dashboard (EPA)	DTXSID101010106
Chemical and physical data
Formula	C11H13NO
Molar mass	175.231 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(N)CC1=CC(C=CO2)=C2C=C1
InChI 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.^[2]

Pharmacology

5-APB is a serotonin–norepinephrine–dopamine reuptake inhibitor with K_i(NET)=180 nmol/L, K_i(DAT)=265 nmol/L and K_i(SERT)=811 nmol/L.^[3] It is also a serotonin–norepinephrine–dopamine releasing agent.^[4] 5-APB is a potent agonist for the 5-HT_2A and 5-HT_2B receptors (K_i of 14 nmol/L at 5-HT_2B with an efficacy of^[3] 0.924). This agonism for 5-HT_2B makes it likely that 5-APB would be cardiotoxic with long term use, as seen in other 5-HT_2B agonists such as fenfluramine and MDMA. ^{[citation needed]} 5-APB is also an agonist of the 5-HT_2C receptor.^[5]

Detection

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.^[6] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.^[7]

Effects

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^[8][9] and solely as the result of 5-APB.^[10]

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.^[11]

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. 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.
4. 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.
5. US patent 7045545, Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03
6. Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135 Archived 2014-05-29 at the Wayback Machine
7. USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf
8. "UCSD student dies of drug overdose after on-campus music festival". Los Angeles Times. August 20, 2014.
9. 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
10. 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.
11. UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.