5-APB: Difference between revisions

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{{Drugbox

| Verifiedfields = changed

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| verifiedrevid = ~~439198969~~

| Watchedfields = changed

| IUPAC_name = 5-(2-aminopropyl)benzofuran

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| verifiedrevid = 458140931

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| image = 5-~~APB_structure~~.~~png~~

| IUPAC_name = 1-(1-Benzofuran-5-yl)propan-2-amine

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| image = 5-APB2DACS.svg

| image2 = 5-APB molecule ball.png

| alt2 = Ball-and-stick model of the 5-APB molecule

| tradename =

| pregnancy_category = ?

| pregnancy_category =

| legal_BR = F2

| legal_status = Uncontrolled

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| legal_UK = Class B

| legal_DE = Anlage II

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| metabolism =

| elimination_half-life =

| excretion =

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| CAS_number =

| CAS_number_Ref = {{cascite|correct|CAS}}

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| CAS_number = 286834-81-9

| UNII_Ref={{fdacite|corect|FDA}}

| UNII = 2M3825704H

| ATC_prefix = none

| ATC_suffix =

| PubChem = 9837232

| synonyms = 1-Benzofuran-5-ylpropan-2-amine

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8012953

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3

| InChIKey = VKUMKUZDZWHMQU-UHFFFAOYAQ

| StdInChI = 1S/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VKUMKUZDZWHMQU-UHFFFAOYSA-N

| C=11 | H=13 | N=1 | O=1

| molecular_weight = 175.23 g/mol

| smiles = CC(N)CC1=CC(C=CO2)=C2C=C1

}}

'''5-(2-aminopropyl)benzofuran''' or '''1-benzofuran-5-ylpropan-2-amine''' ('''5-APB''') is a drug claimed to act as an [[agonist]] of the [[5-HT2C receptor|5-HT2C receptor]],<ref>{{ cite patent

'''5-APB''' (abbreviation of "5-(2-aminopropyl)benzofuran"; see infobox for the correct IUPAC name) is an [[Empathogen-entactogen|empathogenic]] [[psychoactive drug|psychoactive]] compound of the [[substituted benzofuran]], [[substituted amphetamine]] and [[substituted phenethylamine]] classes. 5-APB and [[Benzofury (disambiguation)|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.<ref>http://www.emcdda.europa.eu/publications/implementation-reports/2010 EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA</ref>

==Pharmacology==

5-APB is a [[serotonin–norepinephrine–dopamine reuptake inhibitor]] with ''K''i([[norepinephrine transporter|NET]])=180 nmol/L, ''K''i([[dopamine transporter|DAT]])=265 nmol/L and ''K''i([[serotonin transporter|SERT]])=811 nmol/L.{{r|Iversen2013}} It is also a serotonin–norepinephrine–dopamine releasing agent.<ref>{{cite journal | vauthors = Rickli A, Kopf S, Hoener MC, Liechti ME | title = Pharmacological profile of novel psychoactive benzofurans | journal = British Journal of Pharmacology | volume = 172 | issue = 13 | pages = 3412–25 | date = July 2015 | pmid = 25765500 | pmc = 4500375 | doi = 10.1111/bph.13128 }}</ref> 5-APB is a potent [[agonist]] for the [[5-HT2A receptor|5-HT2A]] and [[5-HT2B receptor|5-HT2B]] receptors (Ki of 14 nmol/L at 5-HT2B with an efficacy of{{r|Iversen2013}} 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|date=September 2017}} 5-APB is also an agonist of the [[5-HT2C|5-HT2C receptor]].<ref>{{ cite patent

| country = US

| number = 7045545

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| gdate = 2006-16-03

| inventor = Karin Briner et al

}}</ref>

}}</ref> which has been sold as a [[designer drug]]. Anecdotal reports from users suggest it has [[stimulant]] and [[empathogen]]ic effects, but less [[psychedelic]] action than related compounds such as [[6-APB]] and [[5-APDB]].{{Citation needed|date=March 2011}}

==Detection==

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.<ref>Southern Association of Forensic Scientists, http://forendex.southernforensic.org/index.php/detail/index/1135 {{Webarchive|url=https://web.archive.org/web/20140529051608/http://forendex.southernforensic.org/index.php/detail/index/1135 |date=2014-05-29 }}</ref> The [[United States Department of Justice|US Department of Justice]] and [[Drug Enforcement Administration|DEA]] have also conducted studies concerning the detection of 5-APB.<ref>USDOJ/DEA, http://www.justice.gov/dea/pr/microgram-journals/2011/mj8-2_62-74.pdf</ref>

==Effects==

Users describe effects as euphoric. Largely, effects reported were similar to that of the drug MDMA but not as strong.{{citation needed|date=February 2014}} Recreational use of 5-APB has been associated with death in combination with other drugs<ref name=LATimes>{{cite news | url = http://www.latimes.com/local/lanow/la-me-ln-ucsd-student-drug-overdose-20140820-story.html | title = UCSD student dies of drug overdose after on-campus music festival | newspaper = [[Los Angeles Times]] | date = August 20, 2014}}</ref><ref>{{cite journal | vauthors = Dawson P, Opacka-Juffry J, Moffatt JD, Daniju Y, Dutta N, Ramsey J, Davidson C | title = The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 48 | pages = 57–63 | date = January 2014 | pmid = 24012617 | doi = 10.1016/j.pnpbp.2013.08.013 | s2cid = 23400101 | url = http://clok.uclan.ac.uk/18222/1/5APB%20in%20press.pdf | quote = 5-APB ... has been implicated in 10 recent drug-related deaths in the UK }}</ref> and solely as the result of 5-APB.<ref>{{cite journal | vauthors = McIntyre IM, Gary RD, Trochta A, Stolberg S, Stabley R | title = Acute 5-(2-aminopropyl)benzofuran (5-APB) intoxication and fatality: a case report with postmortem concentrations | journal = Journal of Analytical Toxicology | volume = 39 | issue = 2 | pages = 156–9 | date = March 2015 | pmid = 25429871 | doi = 10.1093/jat/bku131 | doi-access = free }}</ref>

==~~See also~~==

==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.<ref>{{cite web | url = http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | title = The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | access-date = 2014-03-11 | author = UK Home Office | date = 2014-03-05 | publisher = UK Government}}</ref>

* [[6-APDB]]

* [[5-(2-Aminopropyl)indole]]

* [[EDMA|Ethylenedioxymethamphetamine]]

* [[Indanylaminopropane]]

* [[Naphthylaminopropane]]

* [[Tetralinylaminopropane]]

==References==

== References ==

{{Reflist|refs=

<ref name=Iversen2013>{{cite journal | vauthors = Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL |author6-link=Bryan Roth | title = Neurochemical profiles of some novel psychoactive substances | journal = European Journal of Pharmacology | volume = 700 | issue = 1–3 | pages = 147–51 | date = January 2013 | pmid = 23261499 | pmc = 3582025 | doi = 10.1016/j.ejphar.2012.12.006 }}</ref>

}}

[[Category:~~Amphetamines~~]]

[[Category:Substituted amphetamines]]

[[Category:~~Benzofurans~~]]

[[Category:5-Benzofuranethanamines]]

[[Category:Designer drugs]]

[[Category:Serotonin-norepinephrine-dopamine releasing agents]]

[[Category:Serotonin receptor agonists]]

[[Category:Entactogens and empathogens]]