| Revision as of 18:35, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Saving copy of the {{drugbox}} taken from revid 472062495 of page 6-APB for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 00:47, 2 November 2024 edit 76.174.0.57 (talk) →Pharmacology: Paragraph split. |
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{{short description|Psychoactive drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Drugbox |
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{{Infobox drug |
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| verifiedrevid = 455351623 |
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| Verifiedfields = changed |
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| IUPAC_name = 6-(2-aminopropyl)benzofuran |
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| Watchedfields = changed |
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| image = 6-APB_structure.png |
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| class = ]; ] |
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| image2 = 6-APB Animation2.gif |
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| verifiedrevid = 477225566 |
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| IUPAC_name = 1-(1-Benzofuran-6-yl)propan-2-amine |
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| image = 6APB.svg |
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| image2 = 6-APB molecule ball.png |
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| alt2 = Ball-and-stick model of the 6-APB molecule |
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<!--Clinical data--> |
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<!--Clinical data-->| tradename = |
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| tradename = |
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| legal_DE = Anlage II |
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| legal_UK = Class B |
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| pregnancy_category = ? |
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| legal_CA = Schedule III |
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| legal_status = Uncontrolled |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data-->| routes_of_administration = ], ] |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| onset = 30–60 minutes |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| duration_of_action = 7–10 hours |
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<!--Identifiers--> |
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| excretion = <!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 286834-85-3 --> |
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| CAS_number = 286834-85-3 |
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| CAS_supplemental = <br /> 286834-84-2 (hydrochloride) |
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| CAS_supplemental = 286834-84-2 (]) |
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| ATC_prefix = none |
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| ATC_prefix = None |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 9794343 |
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| PubChem = 9794343 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7970110 |
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| ChemSpiderID = 7970110 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 285VE60914 |
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<!--Chemical data--> |
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<!--Chemical data-->| C = 11 |
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| C=11 | H=13 | N=1 | O=1 |
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| H = 13 |
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| N = 1 |
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| molecular_weight = 175.23 g/mol |
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| O = 1 |
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| smiles = o2c1cc(ccc1cc2)CC(N)C |
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| smiles = NC(C)CC1=CC(OC=C2)=C2C=C1 |
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| InChI = 1/C11H13NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3 |
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| InChIKey = FQDAMYLMQQKPRX-UHFFFAOYAX |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H13NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3 |
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| StdInChI = 1S/C11H13NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3 |
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| StdInChIKey = FQDAMYLMQQKPRX-UHFFFAOYSA-N |
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| StdInChIKey = FQDAMYLMQQKPRX-UHFFFAOYSA-N |
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}} |
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}} |
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'''6-APB''' ('''6-(2-aminopropyl)benzofuran''') is an ] ] of the ] and ] classes.<ref name="pmid23261499" /> 6-APB and ] are sometimes informally called "Benzofury" in newspaper reports. It is ] to ], but differs in that the 3,4-] ] system has been replaced with a ] ring. 6-APB is also the unsaturated benzofuran derivative of ]. It may appear as a tan grainy powder.{{cn|date=October 2024}} |
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While the drug never became particularly popular, it briefly entered the rave and underground clubbing scene in the UK before its sale and import were banned. It falls under the category of ]s, sometimes called "legal highs” if uncontrolled. Because 6-APB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to its popularity.{{cn|date=October 2024}} |
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== Pharmacology == |
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] |
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=== Pharmacodynamics === |
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6-APB is a ] (SNDRI) with K<sub>i</sub> values of 117, 150, and 2698 nM for the ] (NET), ] (DAT), and ] (SERT), respectively.<ref name="pmid23261499">{{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> In addition, 6-APB not only ]s the ] of these ]s but is also a ] of them; that is, it is a ] (SNDRA).<ref name="pmid25765500">{{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> |
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In addition to actions at the ]s, 6-APB is a ] ] of the ] ] (K<sub>i</sub> = 3.7 nM),<ref name="pmid23261499" /> with higher ] for this ] than any other site.<ref name="pmid27903793">{{cite journal | vauthors = Canal CE, Murnane KS | title = 2C receptor and the non-addictive nature of classic hallucinogens | journal = Journal of Psychopharmacology | volume = 31 | issue = 1 | pages = 127–143 | date = January 2017 | pmid = 27903793 | pmc = 5445387 | doi = 10.1177/0269881116677104 }}</ref> Moreover, unlike ], 6-APB shows 100-fold ] for the 5-HT<sub>2B</sub> receptor over the ] and ]s.<ref name="pmid27903793" /><ref name="Briner_2000">{{cite patent | country = US | number = 7045545 | status = patent | title = Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists | pubdate = 19 January 2000 | gdate = 16 May 2006 | inventor = Briner K, Burkhart JP, Burkholder TP, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu YC, Xu Y | assign1 = Eli Lilly Co. }}</ref> It is notably both more potent and more selective as an agonist of the 5-HT<sub>2B</sub> receptor than the reference 5-HT<sub>2B</sub> receptor agonist, ], which is commonly used for research into the 5-HT<sub>2B</sub> receptor.{{Citation needed|date=January 2016}} Aside from the 5-HT<sub>2B</sub> receptor, 6-APB has also been found to bind with high affinity to the ] subtype (K<sub>i</sub> = 45 nM), although the clinical significance of this action is unknown.<ref name="pmid23261499" /> 6-APB showed little other affinity at a wide selection of other sites.<ref name="pmid23261499" /> |
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The potent agonism of the 5-HT<sub>2B</sub> receptor makes it likely that 6-APB would be ] with chronic or long-term use, as seen with other 5-HT<sub>2B</sub> receptor agonists such as the ] ] ] ].<ref name="pmid23261499" /><ref name="ACMD report" /> |
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=== Pharmacokinetics === |
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The ] of 6-APB have not been studied, however, some information can be extracted from user reports. These suggest a slow onset of 40–120 minutes. The drugs peak effects last 7 hours, followed by a comedown phase of approximately 2 hours, and after effects for up to 24 hours.<ref>{{cite book | title=Novel Psychoactive Substances: Classification, Pharmacology and Toxicology Chapter 16 – Benzofurans and Benzodifurans | publisher=Academic Press | author=Shaun L. Greene | date=2013 | location=Boston | pages=383–392 | isbn=978-0-12-415816-0 | doi=10.1016/B978-0-12-415816-0.00016-X}}</ref> |
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==== Metabolism ==== |
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Although limited literature is available, there is some data on ] of 6-APB in rats. Its Phase I metabolism involves ] of the ] ring, then cleavage of the ring, followed by a ] of the unsaturated ] from the previous step. The resulting aldehyde may then take two paths. It is either oxidized to a ] or reduced to an ], and then ]. Phase II metabolism consists of ]. The most prevalent metabolites in rats were ] and ].<ref>{{cite journal | vauthors = Nugteren-van Lonkhuyzen JJ, van Riel AJ, Brunt TM, Hondebrink L | title = Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans | journal = Drug and Alcohol Dependence | volume = 157 | pages = 18–27 | date = December 2015 | pmid = 26530501 | doi = 10.1016/j.drugalcdep.2015.10.011 }}</ref> |
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===Adverse effects=== |
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Acute ] has been associated with recreational use of 6-APB in combination with the synthetic cannabinoid JWH-122.<ref>{{cite journal | vauthors = Chan WL, Wood DM, Hudson S, Dargan PI | title = Acute psychosis associated with recreational use of benzofuran 6-(2-aminopropyl)benzofuran (6-APB) and cannabis | journal = Journal of Medical Toxicology | volume = 9 | issue = 3 | pages = 278–81 | date = September 2013 | pmid = 23733714 | pmc = 3770991 | doi = 10.1007/s13181-013-0306-y }}</ref> |
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== Reagents results == |
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6-APB and its structural isomer ] have been tested with a series of agents including: ], ], ], and ] reagents.<ref>{{Cite web|title=Results|url=https://www.protestkit.eu/results/|access-date=2021-06-01|website=PRO Test|language=en-US}}</ref> Exposing compounds to the reagents gives a colour change which is indicative of the compound under test. |
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{| class="wikitable" |
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!Compound |
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!] |
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!] |
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!] |
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!] |
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!] |
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!Gallic |
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!] |
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!Hofmann |
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!] |
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!] |
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|- |
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|6-APB |
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|Purple |
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|Purple to black |
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|Purple to black |
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|Black |
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|Purple |
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|Brown |
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|Orange |
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|Light orange |
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|No reaction |
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|Light orange |
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|6-APB succinate |
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|Purple |
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|Purple to black |
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|Purple to black |
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|Black |
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|Purple |
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|Brown |
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|Faint orange |
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|No reaction |
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|No reaction |
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|Light orange |
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6-APB succinate is reported to be practically insoluble in ] as well as very minimally soluble in cold ]. A batch seized by the DEA contained a 2:1 ratio of succinate to 6-APB.<ref name="Casale_2012">{{cite journal | url=https://www.dea.gov/pr/microgram-journals/2012/mj9_61-74.pdf | title=The Characterization of 6-(2-Aminopropyl)benzofuran and Differentiation from its 4-, 5-, and 7-Positional Analogues | vauthors = Casale JF, Hays PA | journal=Microgram Journal | date=January 2012 | volume=9 | issue=2 | pages=61–74 | access-date=2016-06-08 | archive-date=2016-11-05 | archive-url=https://web.archive.org/web/20161105053635/https://www.dea.gov/pr/microgram-journals/2012/mj9_61-74.pdf | url-status=dead }}</ref> |
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== Synthesis == |
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] |
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The synthesis by Briner ''et al''.<ref name="Briner_2000" /> entailed refluxing ] with bromoacetaldehyde diethylacetal and ] to give the diethyl ], which then was heated with ] to give a mixture of bromobenzofuran ]s: 4-bromo-1-benzofuran and 6-bromo-1-benzofuran. The isomers were separated by ] ], then converted to their respective propanone derivatives, and then reductively aminated to give 6-APB and 4-APB, both of which were converted to their ] ]s for further examination. |
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== Dosage and duration == |
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{{Citations needed section|date=October 2024}} |
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6-APB can be found in ], ], and ] form. The freebase is purportedly 20% stronger than the ] and 65% stronger than the succinate. This means 100 mg of 6-APB HCl is equivalent to 83 mg of 6-APB freebase and 100 mg of 6-APB succinate is equivalent to 60 mg of 6-APB freebase. Different production batches may have impurities and should be treated with care.{{cn|date=October 2024}} |
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Based on anecdotal reports, the dosages for 6-APB hydrochloride are the following: |
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{| class="wikitable" |
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|+Dosage |
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!Oral |
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|Threshold |
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|15 mg |
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|Light |
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|15–60 mg |
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|Common |
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|60–90 mg |
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|Strong |
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|90–120 mg |
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|Heavy |
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|120 mg + |
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{| class="wikitable" |
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|+Duration |
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!Oral |
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|Onset |
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|30–60 minutes (or more) |
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|Come up |
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|60–120 minutes |
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|Peak |
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|3–4 hours |
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|Offset |
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|2–3 hours |
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|Total |
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|7–10 hours |
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|After effects |
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|6–48 hours |
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The dosages for freebases or succinates have to be adjusted accordingly. |
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== Law == |
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=== North America === |
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==== Canada ==== |
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In 1999, amphetamines were changed from ] to ] as a result of the ]. Some have speculated that 6-APB's structure qualifies it as a Schedule I drug as an ] of MDA.<ref>{{Cite web|url=https://isomerdesign.com/Cdsa/definitions.php?structure=C|title=Controlled Drugs and Substances Act : Definitions and Interpretations|website=isomerdesign.com|access-date=2019-11-11}}</ref>{{Unreliable source?|date=November 2019}} |
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In 2014, a study funded by the ] noted that 6-APB "may or may not be legal in Canada depending on how one interprets the current Act"<ref>{{Cite journal| vauthors = Hudson AL, Lalies MD, Baker GB, Wells K, Aitchison KJ |date=2014-04-16|title=Ecstasy, legal highs and designer drug use: A Canadian perspective|journal= ] |language=en|volume=1|pages=2050324513509190|doi=10.1177/2050324513509190|s2cid=159675835|issn=2050-3245|doi-access=free}}</ref> and that it could be purchased for academic purposes without an exemption from Health Canada. The study also noted how, unlike the MDMA it often serves as a replacement for in countries like the US, 6-APB's ] structure does not make it a direct analogue of ] despite similarities in effects. |
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==== United States ==== |
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6-APB is not scheduled at the federal level in the ],<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. |access-date=2018-04-10 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }}</ref>{{Failed verification|date=June 2019}} but it may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the ].<ref>{{cite journal | vauthors = Casale JF, Hays PA | title = The characterization of 5-and 6-(2-aminopropyl)-2, 3-dihydrobenzofuran. | journal = Microgram J. | date = January 2011 | volume = 8 | issue = 2 | pages = 62–74 | url = https://www.researchgate.net/publication/258111445 }}</ref> |
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=== Finland === |
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6-APB is scheduled in government decree on narcotic substances, preparations and plants and hence is illegal.<ref>{{Cite web |title=Ajantasa |url=https://finlex.fi/fi/laki/ajantasa/2008/20080543 |website=finlex.fi}}</ref> |
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=== France === |
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6-APB is illegal in ].<ref>{{cite web | url=https://www.legifrance.gouv.fr/loda/id/JORFTEXT000000533085/2023-06-23/ | title=Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants }}</ref> |
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=== Germany === |
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6-APB is illegal in ] since the 17th of July, 2013, when it was added to ] of the ].{{cn|date=October 2024}} |
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=== Italy === |
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6-APB is illegal in ].<ref>{{cite web | url=http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf | title=Nuove tabelle delle sostanze stupefacenti e psicotrope (DPR 309/90) | publisher=Ministero della Salute | language=it | access-date=2016-05-31 | archive-date=2016-02-06 | archive-url=https://web.archive.org/web/20160206033837/http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf | url-status=dead }}</ref> |
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=== Luxembourg === |
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In ], 6-APB is not cited in the list of prohibited substances.<ref>{{Cite web|title=Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie. - Legilux|url=http://legilux.public.lu/eli/etat/leg/loi/1973/02/19/n1/jo|access-date=2021-06-01|website=legilux.public.lu}}</ref> Therefore, it is still a legal substance. |
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=== Netherlands === |
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6-APB is not listed under the ] or the Medicine Act in the ], and thus currently legal.{{cn|date=October 2024}} |
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=== New Zealand and Australia === |
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Certain countries contain a "substantially similar" catch-all clause in their drug law, such as ] and ]. This includes 6-APB as it is similar in chemical structure to the class A drug ], meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.<ref>{{cite web | url=http://www.legislation.govt.nz/act/public/1975/0116/latest/DLM436101.html | title=Misuse of Drugs Act 1975 | date=7 November 2015 | publisher=New Zealand Legislation}}</ref> |
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=== Sweden === |
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In ], as of 27 December 2009 6-APB is classified as "health hazard" under the act ] (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'').<ref>{{cite web | url=http://www.notisum.se/rnp/sls/fakta/a9990058.HTM | title=Förordning (1999:58) om förbud mot vissa hälsofarliga varor | publisher=Lagbevakning med Notisum och Rättsnätet | date=24 November 2009 | language=sv | access-date=15 September 2013 | archive-date=4 October 2013 | archive-url=https://web.archive.org/web/20131004215233/http://www.notisum.se/rnp/sls/fakta/a9990058.HTM | url-status=dead }}</ref> |
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=== UK === |
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On June 10, 2013 6-APB and a number of analogues were classified as ] in the UK following an ACMD recommendation.<ref name="ACMD report">{{cite web | url=https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | title=Temporary class drug order on benzofury and NBOMe compounds - letter from ACMD | publisher=GOV.UK | date=4 June 2013 | work = Advisory Council on the Misuse of Drugs | vauthors = Browne J }}</ref> This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.<ref>{{cite news | url=https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned | title='NBOMe' and 'Benzofury' banned | date=4 June 2013 | agency=GOV.UK | work = Home Office | vauthors = Browne J }}</ref> On November 28, 2013 the ACMD recommended that 6-APB and related benzofurans should become ], ] substances.<ref name="ACMD report" /> 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.<ref>{{cite web | url=http://www.legislation.gov.uk/uksi/2014/1106/contents/made | title=The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | publisher=The National Archives | date=28 April 2014 | author=UK Home Office}}</ref> |
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=== China === |
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6-APB has been a controlled substance in China since 1 July 2024<ref>{{Cite web |last=National Medical Products Administration (NMPA) of China |date=July 22, 2024 |title=关于将溴啡等46种物质列入《非药用类麻醉药品和精神药品管制品种增补目录》的公告 |url=https://www.nmpa.gov.cn/xxgk/ggtg/ypggtg/ypqtggtg/20240619150650124.html}}</ref> |
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== References == |
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{{Reflist}} |
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{{Entactogens|state=expanded}} |
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{{Hallucinogens}} |
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{{Phenethylamines}} |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |