5-APB

5-APB
Clinical data
Other names	1-Benzofuran-5-ylpropan-2-amine
ATC code	none;
Legal status
Legal status	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 ;
PubChem CID	9837232;
ChemSpider	8012953 ;
UNII	2M3825704H;
CompTox Dashboard (EPA)	DTXSID101010106 ;
Chemical and physical data
Formula	C11H13NO
Molar mass	175.23 g/mol 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 ; Key:VKUMKUZDZWHMQU-UHFFFAOYSA-N ;
	(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

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.^[2] It is also a serotonin–norepinephrine–dopamine releasing agent.^[3] 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^[2] 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.^[4]

Detection

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

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

Legality

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.^[10]

References

^ 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, 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 3582025. PMID 23261499.
^ 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 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. {{cite news}}: Italic or bold markup not allowed in: |publisher= (help)
^ 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
^ McIntyre, Iain M; Gary, Ray D; Trochta, Amber; Stolberg, Susan; Stabley, Robert (2015). "Acute 5-(2-Aminopropyl)Benzofuran (5-APB) Intoxication and Fatality: A Case Report with Postmortem Concentrations". Journal of Analytical Toxicology. 39 (2): 156. 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.

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

[Iversen2013-2] 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 3582025. 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 4500375. 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 Archived 2014-05-29 at the Wayback Machine

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

[LATimes-7] "UCSD student dies of drug overdose after on-campus music festival". Los Angeles Times. August 20, 2014. {{cite news}}: Italic or bold markup not allowed in: |publisher= (help)

[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] McIntyre, Iain M; Gary, Ray D; Trochta, Amber; Stolberg, Susan; Stabley, Robert (2015). "Acute 5-(2-Aminopropyl)Benzofuran (5-APB) Intoxication and Fatality: A Case Report with Postmortem Concentrations". Journal of Analytical Toxicology. 39 (2): 156. doi:10.1093/jat/bku131. PMID 25429871.

[10] UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.

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v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MAPBT 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine