6-APB

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6-APB


Systematic (IUPAC) name
6-(2-aminopropyl)benzofuran
Clinical data
Legal status	?
Identifiers
CAS number	286834-85-3^N 286834-84-2 (hydrochloride)
ATC code	None
PubChem	CID 9794343
ChemSpider	7970110^Y
Chemical data
Formula	C₁₁H₁₃N O
Mol. mass	175.23 g/mol
SMILES NC(C)CC1=CC(OC=C2)=C2C=C1
InChI InChI=1S/C11H13NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3^Y Key:FQDAMYLMQQKPRX-UHFFFAOYSA-N^Y
N (what is this?) (verify)

6-(2-aminopropyl)benzofuran or 1-benzofuran-6-ylpropan-2-amine (6-APB), also known as Benzofury is an entactogenic compound of the phenethylamine and amphetamine classes. It is similar in structure to MDA but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB.

Pharmacology

6-APB is a triple monoamine reuptake inhibitor with K_i values of 117, 150 and 2698 for NET, DAT and SERT respectively as well as being a potent agonist for the 5-HT_2B receptor (K_i 3.7nM).^[1] The subjective effects and structure–activity relationship suggest that it is also a releasing agent.

The agonism for 5-HT_2B makes it likely that 6-APB would be cardiotoxic with long term use, as seen in other 5-HT_2B agonists such as fenfluramine and MDMA.^[2]^[1] 6-APB has also been claimed to act as an agonist of the 5-HT_2C receptor and therefore may be useful as an appetite suppressant.^[3] However while 6-APB is an agonist at all three 5-HT₂ receptor subtypes, its potency at 5-HT_2B is significantly higher, and it is actually both more potent and more selective over other serotonin receptors than the reference agonist BW723C86 which is commonly used for research into 5-HT_2B receptors.

Effects

The drug, normally taken in pill form^{[citation needed]} (although powdered forms have also been administered) usually takes effect within 45 minutes to an hour. After which time, users have reported feeling a sense of overwhelming euphoria, combined with a surge of energy, reaching a plateau after approximately 2 hours, and lasting up to 10 hours after initial administration.^[4] Users have also reported very strong feelings of empathy towards others, as well as musical euphoria (that is a strong connection with the particular music they are listening to).^[5] While the drug never became particularly popular, it briefly entered the rave and underground clubbing scene in Britain, before its sale and import were banned.

Law

6-APB is not listed under the Opium Law or the Medicine Act in the Netherlands, and thus currently legal.

6-APB is unscheduled in the United States, but not currently approved by the Food and Drug Administration for human consumption.

Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APB as it is in some respects similar in chemical structure to the class A drug MDA^{[citation needed]}, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.^[6]

6-APB is unscheduled under the Controlled Drugs and Substances Act (CDSA) in Canada, although there is a Schedule III amphetamine analogue clause. Due to 6-APB's structure, it may be considered an analogue of MDA, but these types of offenses are rarely prosecuted.^{[citation needed]} Canada's CDSA defines an analogue as any substance that, in relation to a controlled substance, has a substantially similar chemical structure.

6-APB is unscheduled in France and Italy.

On June 10, 2013 6-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.^[2] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.^[7] On November 28th, 2013 the ACMD recommended that 6-APB and related benzofurans should become Class B, Schedule 1 substances.^[2]

6-APB is illegal in Germany since the 17th of July, 2013, when it was added to the Betäubungsmittelgesetz.^[8]

In Sweden, 6-APB is classified as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of December 27, 2009 under SFS 2009:1095^[9] making it illegal to sell or possess.

References

↑ 1.0 1.1 Iversen, L.; Gibbons, S.; Treble, R.; Setola, V.; Huang, X. P.; Roth, B. L. (2012). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. doi:10.1016/j.ejphar.2012.12.006.
↑ 2.0 2.1 2.2 "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 04 Jun 2013. Retrieved 2013-06-13.
↑ US patent 7045545, Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03
↑ "Party Vibe Forums - Benzo Fury".
↑ "Experiences - "Benzo Fury" Experiences".
↑ "Misuse of Drugs Act 1975 New Zealand.". legislation.govt.nz. Archived from the original on 28 July 2010. Retrieved 2010-08-06.
↑ "'NBOMe' and 'Benzofury' banned". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13.
↑ 'bgbl113037.pdf'%5D&wc=1&skin=WC#__Bundesanzeiger_BGBl__%2F%2F*%5B%40attr_id%3D'bgbl113s2274.pdf'%5D__1377728719705|Siebenundzwanzigste Verordnung zur Änderung von betäubungsmittelrechtlichen Vorschriften, Art. 1 VO vom 9. Juli 2013(BGBl. I S. 2274)
↑ http://www.notisum.se/rnp/sls/fakta/a9990058.HTM

Hallucinogens

Psychedelics
5-HT_2AR agonists

Lysergamides	AL-LAD ALD-52 BU-LAD CYP-LAD IP-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 Lysergic acid 2-butyl amide LSZ Lysergic acid 3-pentyl amide Methylergometrine Methylisopropyllysergamide Methysergide N1-Methyl-lysergic acid diethylamide PARGY-LAD PRO-LAD

Phenethylamines	Aleph 2-Methyl-MDA 2C-B 2C-B-Dragonfly 2C-B-FLY βk-2C-B 2C-C 2C-C-FLY 25C-NBOMe 25CN-NBOH 25CN-NBOMe 25D-NBOMe 2C-D 2C-D-FLY 2C-E 2C-E-FLY 2C-E-NBOMe 2C-EF 2C-F 2C-F-NBOMe 2C-G 2C-G-NBOMe 2C-H-NBOMe 2C-I 2C-I-FLY 2C-N 25N-NBOMe 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-4 2C-T-4-NBOMe 2C-T-7 2C-T-7-FLY 2C-T-7-NBOH 2C-T-8 2C-T-13 2C-T-15 2C-T-17 2C-T-19 2C-T-21 2C-TFM 25TFM-NBOMe 2C-YN 2CBCB-NBOMe 2CBFly-NBOMe 2CD-5EtO 25B-NBOMe 25C-NBOH 25I-NBMD 25I-NBOH 25I-NBOMe 2C-P-NBOMe 3C-AL 3C-E 3C-P 5-APB 5-APDB 5-APDI 5-Methyl-MDA 6-APB 6-APDB 6-Methyl-MDA Br-DFLY DESOXY DMMDA DMMDA-2 DOB DOB-FLY DOC DOEF DOET DOF DOI DOM DOM-FLY DON DOPR DOTFM Escaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Jimscaline Juncosamine Lophophine Macromerine MDA MDEA MDMA Mescaline Methallylescaline MMA MMDA MMDA-2 MMDA-3a MMDMA NBOMe-mescaline Proscaline TCB-2 TFMFly TMA

Piperazines	pFPP TMFPP mCPP

Tryptamines	1-Methyl-5-methoxy-diisopropyltryptamine 2,N,N-TMT 4,5-DHP-AMT 4,5-DHP-DMT 4-Acetoxy-DALT 4-Acetoxy-DET 4-Acetoxy-DiPT 4-Acetoxy-DMT 4-Acetoxy-DPT 4-Acetoxy-MiPT 4-HO-5-MeO-DMT 4-HO-DBT 4-HO-DPT 4-HO-MET 4-HO-MPMI 4-HO-MPT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-Me-MIPT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-MET 5-MeO-MiPT 5-MeO-MPMI 5-N,N-TMT 7,N,N-TMT α-ET α-MT α,N,N-TMT Aeruginascin Baeocystin Bufotenin DALT DBT DCPT DET DIPT DMT DPT EiPT Ethocin Ethocybin Iprocin MET Miprocin MiPT Norbaeocystin PiPT Psilocin Psilocybin

Others	AL-38022A Elemicin Ibogaine Myristicin Noribogaine Voacangine

Dissociatives
NMDAR antagonists

Adamantanes	Amantadine Memantine Rimantadine

Arylcyclohexylamines	3-MeO-PCP 4-MeO-PCP Dieticyclidine Diphenidine Esketamine Ethketamine Eticyclidine Gacyclidine Ketamine Methoxetamine Methoxyketamine Neramexane PCPr Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Morphinans	Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others	2-MDP 8A-PDHQ Aptiganel Dexoxadrol Dizocilpine Etoxadrol Ibogaine Midafotel NEFA Nitrous oxide Noribogaine Perzinfotel Remacemide Selfotel Xenon

Deliriants
mAChR antagonists

Miscellaneous

Cannabinoids
CB₁R agonists

Phytocannabinoids	Cannabinol THC (Dronabinol) THCV (Cannabidiol has different mechanism of action)

Synthetic	CP 47,497 CP 55,244 CP 55,940 DMHP HU-210 JWH-018 JWH-030 JWH-073 JWH-081 JWH-200 JWH-250 Levonantradol Nabilone Nabitan Parahexyl WIN 55,212-2

D₂R agonists

Aporphine
Bromocriptine
Cabergoline
Lisuride
Memantine
Nuciferine
Pergolide
Piribedil
Pramipexole
Ropinirole
Rotigotine
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_AR agonists

Inhalants
Mixed MOA

κOR agonists

MAO inhibitors

σR agonists

Others

v t e Phenethylamines

Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-17 2C-T-21 2C-TFM 2C-YN 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 N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine 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: 3-FMA 4-MA 4-MMA 4-MTA 5-IT Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Fludorex Furfenorex Gepefrine Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Norfenfluramine L-Norpseudoephedrine Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 5-APB 5-APDB 5-MAPB 6-APB 6-APDB EDA IAP MDA MDEA MDHMA MDMA MDOH MMDMA NAP TAP Others: Amiflamine DFMDA Selegiline (also D-Deprenyl)

Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH

Cathinones	Stimulants: Amfepramone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Flephedrone Methcathinone Mephedrone Methedrone Entactogens: Ethylone Methylone

Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine

Phenylalkylpyrrolidines	Stimulants: a-PBP a-PPP a-PVP MDPBP MDPPP MDPV MOPPP 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	Amidephrine Arbutamine Cafedrine Denopamine Dobutamine Dopexamine Etafedrine Famprofazone Hexapradol Methoxamine Pronethalol Salbutamol (Levosalbutamol) Theodrenaline UWA-101

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6-APB

Pharmacology

Effects

Law

See also

References