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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 names1-Benzofuran-5-ylpropan-2-amine
ATC code
  • none
Legal status
Legal status
Identifiers
  • 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
FormulaC11H13NO
Molar mass175.231 g·mol−1
3D model (JSmol)
  • Interactive image
  • CC(N)CC1=CC(C=CO2)=C2C=C1
  • 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 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.[3] It is also a serotonin–norepinephrine–dopamine releasing agent.[4] 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[3] 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.[5]

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.[6] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[7]

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

Legality edit

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 edit

  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). 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. ^ a b 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 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.

abbreviation, aminopropyl, benzofuran, infobox, correct, iupac, name, empathogenic, psychoactive, compound, substituted, benzofuran, substituted, amphetamine, substituted, phenethylamine, classes, other, compounds, sometimes, informally, called, benzofury, cli. 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 APBClinical dataOther names1 Benzofuran 5 ylpropan 2 amineATC codenoneLegal statusLegal statusBR Class F2 Prohibited psychotropics 1 DE Anlage II Authorized trade only not prescriptible UK Class BIdentifiersIUPAC name 1 1 Benzofuran 5 yl propan 2 amineCAS Number286834 81 9 YPubChem CID9837232ChemSpider8012953 YUNII2M3825704HCompTox Dashboard EPA DTXSID101010106Chemical and physical dataFormulaC 11H 13N OMolar mass175 231 g mol 13D model JSmol Interactive imageSMILES CC N CC1 CC C CO2 C2C C1InChI 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 YKey VKUMKUZDZWHMQU UHFFFAOYSA N Y N Y 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 Contents 1 Pharmacology 2 Detection 3 Effects 4 Legality 5 ReferencesPharmacology edit5 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 3 It is also a serotonin norepinephrine dopamine releasing agent 4 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 3 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 5 Detection editA 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 editUsers 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 editOn 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 edit Anvisa 2023 07 24 RDC Nº 804 Listas de Substancias Entorpecentes Psicotropicas 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 Diario Oficial da Uniao published 2023 07 25 Archived from the original on 2023 08 27 Retrieved 2023 08 27 http www emcdda europa eu publications implementation reports 2010 EMCDDA Europol 2010 Annual Report on the implementation of Council Decision 2005 387 JHA a b 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 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 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 Archived 2014 05 29 at the Wayback 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 amp 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 Retrieved 2014 03 11 Retrieved from https en wikipedia org w index php title 5 APB amp oldid 1181593764, wikipedia, wiki, book, books, library,

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