Chemistry:5-EAPB

5-EAPB
Clinical data
Pregnancy; category	?;
ATC code	none;
Legal status
Legal status	BR: F2 ; CA: Schedule I ; DE: NpSG (Industrial and scientific use only) ; UK: Class B ;
Identifiers
	IUPAC name 1-(1-Benzofuran-5-yl)-N-ethylpropan-2-amine;
CAS Number	1445566-01-7 ;
ChemSpider	32078888;
UNII	889D8VM2SL;
Chemical and physical data
Formula	C13H17NO
Molar mass	203.28 g/mol (freebase) 239.78 g/mol (hydrochloride) g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(NCC)CC1=CC(C=CO2)=C2C=C1;
	InChI InChI=1S/C13H17NO/c1-3-14-10(2)8-11-4-5-13-12(9-11)6-7-15-13/h4-7,9-10,14H,3,8H2,1-2H3; Key:ZBZDDOARNPAMSP-UHFFFAOYSA-N;

Short description: Chemical compound

5-EAPB (1-(benzofuran-5-yl)-N-ethylpropan-2-amine) is a potentially entactogenic amphetamine which is structurally related to 5-MAPB and 5-APB. It might be predicted to show similar effects to these drugs in humans, but the pharmacology of 5-EAPB remains unstudied as of 2020.

5-EAPB is similar in structure to compounds such as 5-APB which are claimed to be agonists of the 5-HT_2C receptor^[1] as well as a triple monoamine reuptake inhibitor, however 5-EAPB is not listed as an example in this patent, and it is not yet established to what extent the activity of 5-EAPB resembles that of 5-APB.

Legality

In the UK, all benzofurans are considered Class B drugs^[2] and are therefore illegal.

5-EAPB is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.^[3]

Adverse reactions and deaths

Three people in their 30s were hospitalised after each taking approximately 500 mg of 5-EAPB, one of whom later died in hospital, whilst attending Brownstock music festival in Essex, UK on August 31, 2013.^[4]

References

↑ Briner K, Burkhart P, Burkholder P, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu YX, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", US patent 7045545, published 2000-01-19, issued 2006-16-03
↑ "Ban on NBOMe and benzofurans comes into force". Gov.uk. 10 June 2014. https://www.gov.uk/government/news/ban-on-nbome-and-benzofurans-comes-into-force.
↑ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. http://www.cnb.gov.sg/Libraries/CNB_Newsroom_Files/CNB_NR_-_30_Apr_2015.sflb.ashx.
↑ "Festivalgoer's death prompts drug warning.". The Guardian. 1 September 2013. https://www.mirror.co.uk/news/uk-news/brownstock-music-festival-goer-dies-after-2244077.

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Original source: https://en.wikipedia.org/wiki/5-EAPB. Read more

[1] Briner K, Burkhart P, Burkholder P, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu YX, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", US patent 7045545, published 2000-01-19, issued 2006-16-03

[2] "Ban on NBOMe and benzofurans comes into force". Gov.uk. 10 June 2014. https://www.gov.uk/government/news/ban-on-nbome-and-benzofurans-comes-into-force.

[3] "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. http://www.cnb.gov.sg/Libraries/CNB_Newsroom_Files/CNB_NR_-_30_Apr_2015.sflb.ashx.

[4] "Festivalgoer's death prompts drug warning.". The Guardian. 1 September 2013. https://www.mirror.co.uk/news/uk-news/brownstock-music-festival-goer-dies-after-2244077.

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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 DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihydrobenzofurans: 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 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 ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC Brephedrone Butylone 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 α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 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 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 Phenpromethamine 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

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Clinical data


Pregnancy category	?
ATC code	none
Legal status
Legal status	BR: F2 CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name 1-(1-Benzofuran-5-yl)-N-ethylpropan-2-amine
CAS Number	1445566-01-7^N
ChemSpider	32078888
UNII	889D8VM2SL
Chemical and physical data
Formula	C₁₃H₁₇NO
Molar mass	203.28 g/mol (freebase) 239.78 g/mol (hydrochloride) g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(NCC)CC1=CC(C=CO2)=C2C=C1
InChI InChI=1S/C13H17NO/c1-3-14-10(2)8-11-4-5-13-12(9-11)6-7-15-13/h4-7,9-10,14H,3,8H2,1-2H3 Key:ZBZDDOARNPAMSP-UHFFFAOYSA-N

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