5-APB

5-APB
Clinical data
Other names	1-Benzofuran-5-ylpropan-2-amine
ATC code	none;
Legal status
Legal status	BR:Class F2(Prohibited psychotropics); 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;
PubChemCID	9837232;
ChemSpider	8012953;
UNII	2M3825704H;
CompTox Dashboard(EPA)	DTXSID101010106;
Chemical and physical data
Formula	C11H13NO
Molar mass	175.231g·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; Key:VKUMKUZDZWHMQU-UHFFFAOYSA-N;
	(what is this?)(verify)

5-APB(abbreviation of "5-(2-aminopropyl)benzofuran "; see infobox for the correct IUPAC name) is anempathogenic psychoactivecompound of thesubstituted benzofuran,substituted amphetamineandsubstituted phenethylamineclasses. 5-APB andother compoundsare 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 adesigner drugsince 2010.^[2]

Pharmacology

5-APB is aserotonin–norepinephrine–dopamine reuptake inhibitorwithK_i(NET)=180 nmol/L,K_i(DAT)=265 nmol/L andK_i(SERT)=811 nmol/L.^[3]It is also a serotonin–norepinephrine–dopamine releasing agent.^[4]5-APB is a potentagonistfor the5-HT_2Aand5-HT_2Breceptors (K_iof 14 nmol/L at 5-HT_2Bwith an efficacy of^[3]0.924). This agonism for 5-HT_2Bmakes it likely that 5-APB would be cardiotoxic with long term use, as seen in other 5-HT_2Bagonists such asfenfluramineandMDMA.^{[citation needed]}5-APB is also an agonist of the5-HT_2Creceptor.^[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]TheUS Department of JusticeandDEAhave 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

^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).Archivedfrom the original on 2023-08-27.Retrieved2023-08-27.
^http://www.emcdda.europa.eu/publications/implementation-reports/2010EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
^^a ^bIversen 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.PMC3582025.PMID 23261499.
^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.PMC4500375.PMID 25765500.
^US patent 7045545,Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03
^Southern Association of Forensic Scientists,http://forendex.southernforensic.org/index.php/detail/index/1135 Archived2014-05-29 at theWayback Machine
^USDOJ/DEA,http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf
^"UCSD student dies of drug overdose after on-campus music festival".Los Angeles Times.August 20, 2014.
^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
^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.
^UK Home Office (2014-03-05)."The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014".UK Government.Retrieved2014-03-11.

[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).Archivedfrom the original on 2023-08-27.Retrieved2023-08-27.

[2] ttp://www.emcdda.europa.eu/publications/implementation-reports/2010EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA

[Iversen2013-3] 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.PMC3582025.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.PMC4500375.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 Archived2014-05-29 at theWayback Machine

[7] USDOJ/DEA,http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf

[LATimes-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.Retrieved2014-03-11.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]