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6-APDB: Difference between revisions
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'''6-APDB''' (also known as '''6-(2-aminopropyl)-2,3-dihydrobenzofuran''' or '''4-Desoxy-MDA''') is a [[stimulant]] and [[Psychoactive class::entactogen]]ic [[research chemical]] of the [[Chemical class::phenethylamine]] and [[Chemical class::benzofuran|benzofuran]] classes. It is a closely related synthetic analogue of [[MDA]] and [[6-APB]] and broadly shares the characteristics of serotonin-selective triple [[monoamine releasers]] and [[reuptake inhibitors]] associated with other [[entactogen]]ic or [[empathogen]]ic compounds. | '''6-APDB''' (also known as '''6-(2-aminopropyl)-2,3-dihydrobenzofuran''' or '''4-Desoxy-MDA''') is a [[stimulant]] and [[Psychoactive class::entactogen]]ic [[research chemical]] of the [[Chemical class::phenethylamine]] and [[Chemical class::benzofuran|benzofuran]] classes. It is a closely related synthetic analogue of [[MDA]] and [[6-APB]] and broadly shares the characteristics of serotonin-selective triple [[monoamine releasers]] and [[reuptake inhibitors]] associated with other [[entactogen]]ic or [[empathogen]]ic compounds. | ||
6-APDB was first synthesized and studied along with [[5-APDB]] in 1993 by [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]]<ref> | 6-APDB was first synthesized and studied along with [[5-APDB]] in 1993 by [[David E. Nichols]] as a potential non-neurotoxic alternative to [[MDMA]]<ref>{{cite journal | vauthors=((Monte, A. P.)), ((Marona-Lewicka, D.)), ((Cozzi, N. V.)), ((Nichols, D. E.)) | journal=Journal of Medicinal Chemistry | title=Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine | volume=36 | issue=23 | pages=3700–3706 | date=12 November 1993 | issn=0022-2623 | doi=10.1021/jm00075a027}}</ref>. It did not come into popular recreational use until over a decade later, where it briefly entered the rave scene and global research chemicals market, in particular the "legal highs" market in the U.K., before its sale and import were subsequently banned. | ||
Because 6-APDB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity as a substitute or replacement for serotonergic entactogens like MDMA or MDA, and are typically distributed through the online research chemicals grey market. | Because 6-APDB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity as a substitute or replacement for serotonergic entactogens like MDMA or MDA, and are typically distributed through the online research chemicals grey market. | ||
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==Pharmacology== | ==Pharmacology== | ||
6-APDB acts as a [[releasing agent]] and triple [[reuptake inhibitor]] of the monoamine [[neurotransmitters]] known as [[serotonin]], [[dopamine]] and [[noradrenaline]]<ref> | 6-APDB acts as a [[releasing agent]] and triple [[reuptake inhibitor]] of the monoamine [[neurotransmitters]] known as [[serotonin]], [[dopamine]] and [[noradrenaline]]<ref>{{cite journal | vauthors=((Iversen, L.)), ((Gibbons, S.)), ((Treble, R.)), ((Setola, V.)), ((Huang, X.-P.)), ((Roth, B. L.)) | journal=European journal of pharmacology | title=Neurochemical Profiles of some novel psychoactive substances | volume=700 | issue=1–3 | pages=147–151 | date=30 January 2013 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3582025/ | issn=0014-2999 | doi=10.1016/j.ejphar.2012.12.006}}</ref> which are the global [[neurotransmitters]] that modulate the brain's ability to feel pleasure, motivation, reward, planning, attention and focus. This is done by promoting the release and inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse through release into the synaptic cleft, essentially allowing them to accumulate and render them liable for immediate reuse. The net result is excitation in a manner which causes a combination of physically stimulating, relaxing, disinhibiting and euphoric effects.<ref>{{cite journal | vauthors=((Fleckenstein, A. E.)), ((Volz, T. J.)), ((Riddle, E. L.)), ((Gibb, J. W.)), ((Hanson, G. R.)) | journal=Annual Review of Pharmacology and Toxicology | title=New Insights into the Mechanism of Action of Amphetamines | volume=47 | issue=1 | pages=681–698 | date=1 February 2007 | url=https://www.annualreviews.org/doi/10.1146/annurev.pharmtox.47.120505.105140 | issn=0362-1642 | doi=10.1146/annurev.pharmtox.47.120505.105140}}</ref> | ||
The unsaturated benzofuran derivative [[6-APB]], or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between [[6-APB]] and 6-APDB has yet to be fully elucidated. | The unsaturated benzofuran derivative [[6-APB]], or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between [[6-APB]] and 6-APDB has yet to be fully elucidated. | ||
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==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | {{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | ||
Due to only having a short history of human use, the toxicity and harm potential is not exactly known. Due to its similarity to MDMA, it is likely that the administration of repeated or high dosages of 6-APDB can be neurotoxic and cardiotoxic<ref>Drug-induced Valvulopathy: An Update | | Due to only having a short history of human use, the toxicity and harm potential is not exactly known. Due to its similarity to MDMA, it is likely that the administration of repeated or high dosages of 6-APDB can be neurotoxic and cardiotoxic<ref name="Elangbam2010">{{cite journal | vauthors=((Elangbam, C. S.)) | journal=Toxicologic Pathology | title=Drug-induced Valvulopathy: An Update | volume=38 | issue=6 | pages=837–848 | date= October 2010 | url=http://journals.sagepub.com/doi/10.1177/0192623310378027 | issn=0192-6233 | doi=10.1177/0192623310378027}}</ref><ref name="Droogmans2007">{{cite journal | vauthors=((Droogmans, S.)), ((Cosyns, B.)), ((D’haenen, H.)), ((Creeten, E.)), ((Weytjens, C.)), ((Franken, P. R.)), ((Scott, B.)), ((Schoors, D.)), ((Kemdem, A.)), ((Close, L.)), ((Vandenbossche, J.-L.)), ((Bechet, S.)), ((Van Camp, G.)) | journal=The American Journal of Cardiology | title=Possible association between 3,4-methylenedioxymethamphetamine abuse and valvular heart disease | volume=100 | issue=9 | pages=1442–1445 | date=1 November 2007 | issn=0002-9149 | doi=10.1016/j.amjcard.2007.06.045}}</ref> in some form. | ||
The [[Toxicity::exact toxic dosage is unknown]]. It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug. | The [[Toxicity::exact toxic dosage is unknown]]. It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug. | ||
===Short-term health concerns=== | ===Short-term health concerns=== | ||
Short-term physical health risks of 6-APDB consumption include [[dehydration]], [[insomnia]], and hyperthermia.<ref>Drug-induced hyperthermia | | Short-term physical health risks of 6-APDB consumption include [[dehydration]], [[insomnia]], and hyperthermia.<ref>{{cite journal | vauthors=((Nimmo, S. M.)), ((Kennedy, B. W.)), ((Tullett, W. M.)), ((Blyth, A. S.)), ((Dougall, J. R.)) | journal=Anaesthesia | title=Drug-induced hyperthermia | volume=48 | issue=10 | pages=892–895 | date= October 1993 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1365-2044.1993.tb07423.x | issn=0003-2409 | doi=10.1111/j.1365-2044.1993.tb07423.x}}</ref> Continuous activity without sufficient rest or rehydration may cause body temperature to rise to dangerous levels, and loss of fluid via excessive perspiration puts the body at further risk as the stimulatory and euphoric qualities of the drug may render the user oblivious to their energy expenditure for quite some time. Diuretics such as alcohol may exacerbate these risks further, although this is known to be more of a problem for MDMA than it is 6-APDB. | ||
Although it has not been formally studied, like with MDMA, small changes in ambient temperature may cause large changes in 6-APDB-induced serotonin neurotoxicity and core body temperature in the rat.<ref>( | Although it has not been formally studied, like with MDMA, small changes in ambient temperature may cause large changes in 6-APDB-induced serotonin neurotoxicity and core body temperature in the rat.<ref>{{cite journal | vauthors=((Malberg, J. E.)), ((Seiden, L. S.)) | journal=The Journal of Neuroscience: The Official Journal of the Society for Neuroscience | title=Small changes in ambient temperature cause large changes in 3,4-methylenedioxymethamphetamine (MDMA)-induced serotonin neurotoxicity and core body temperature in the rat | volume=18 | issue=13 | pages=5086–5094 | date=1 July 1998 | issn=0270-6474}}</ref><ref>{{cite journal | vauthors=((Wolff, K.)), ((Tsapakis, E. M.)), ((Winstock, A. R.)), ((Hartley, D.)), ((Holt, D.)), ((Forsling, M. L.)), ((Aitchison, K. J.)) | journal=Journal of Psychopharmacology | title=Vasopressin and oxytocin secretion in response to the consumption of ecstasy in a clubbing population | volume=20 | issue=3 | pages=400–410 | date= May 2006 | url=http://journals.sagepub.com/doi/10.1177/0269881106061514 | issn=0269-8811 | doi=10.1177/0269881106061514}}</ref> | ||
===Long-term health concerns=== | ===Long-term health concerns=== | ||
The neurotoxicity of 6-APDB is controversial. It was specifically designed to be less neurotoxic than MDA or MDMA by circumventing the production of certain metabolic byproducts thought to underlie their toxicity (specifically alpha-methyl-dopamine).{{Citation needed}} Although it is likely to be physically safe to try in a responsible context, it is completely possible that the administration of repeated or high dosages of 6-APDB could result in neurotoxic effects in some form, possibly manifesting as deficits in cognitive, affective and psychomotor function. | The neurotoxicity of 6-APDB is controversial. It was specifically designed to be less neurotoxic than MDA or MDMA by circumventing the production of certain metabolic byproducts thought to underlie their toxicity (specifically alpha-methyl-dopamine).{{Citation needed}} Although it is likely to be physically safe to try in a responsible context, it is completely possible that the administration of repeated or high dosages of 6-APDB could result in neurotoxic effects in some form, possibly manifesting as deficits in cognitive, affective and psychomotor function. | ||
As with MDMA, long-term heavy use of 6-APDB is likely cardiotoxic and thought to lead to valvulopathy through its actions on the 5-HT2B receptor.<ref | As with MDMA, long-term heavy use of 6-APDB is likely cardiotoxic and thought to lead to valvulopathy through its actions on the 5-HT2B receptor.<ref name="Elangbam2010"/><ref name="Droogmans2007"/> | ||
===Tolerance and addiction potential=== | ===Tolerance and addiction potential=== | ||
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There is an increased risk of serotonin syndrome when 6-APDB is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if 6-APDB is taken with SSRIs and SNRIs, the 6-APDB will be significantly less powerful or may have no distinguishable effects at all. | There is an increased risk of serotonin syndrome when 6-APDB is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if 6-APDB is taken with SSRIs and SNRIs, the 6-APDB will be significantly less powerful or may have no distinguishable effects at all. | ||
==Legal | ==Legal status== | ||
*'''Australia and New Zealand''': Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APDB as it is similar in chemical structure to the class A drug MDA, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.{{citation needed}} | |||
*'''Canada | *'''Canada''': 6-APDB is Schedule III in Canada as it is an analogue of MDA. The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.{{citation needed}} | ||
*'''United Kingdom | *'''France''': 6-APDB is classified as a narcotic since May 9, 2018, alongside other substances derived from benzofuran.<ref>{{cite web|url=https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000043529751|title=Article Annexe IV - Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants|publisher=Légifrance|access-date=September 23, 2022|language=fr}}</ref> | ||
*'''United States | *'''Germany''': 6-APDB is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 18, 2019|language=de}}</ref> as of November 26, 2016.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 18, 2019|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 18, 2019|language=de}}</ref> | ||
*'''Italy''': 6-APDB is a prohibited substance in Italy.<ref>http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref> | |||
*'''Sweden''': 6-APDB is prohibited in Sweden as a "health hazard" as of 2009.{{citation needed}} | |||
*'''Switzerland''': 6-APDB is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | |||
*'''United Kingdom''': On June 10, 2013, 6-APDB and a number of analogues were classified as Temporary Class Drugs in the U.K. following an ACMD recommendation. On March 5, 2014, the U.K. Home Office announced that 6-APDB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.<ref>{{Citation | title=The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | url=https://www.legislation.gov.uk/uksi/2014/1106/contents/made}}</ref> | |||
*'''United States''': 6-APDB is unscheduled in the United States. It may be considered an analog of [[MDA]] (which is a Schedule I drug under the Controlled Substances Act). As such, the sale and possession for the purposes of human consumption or could be prosecuted as crimes under the Federal Analog Act.{{citation needed}} | |||
==See also== | ==See also== | ||
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[[Category:Entactogen]] | [[Category:Entactogen]] | ||
[[Category:Stimulant]] | [[Category:Stimulant]] | ||
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