6-APDB
{{Short description|Stimulant designer drug}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 477225590
| image = 4-desoxy-MDA.svg
| width =
| image2 = 6-APDB molecule ball.png
| alt2 = Ball-and-stick model of the 6-APDB molecule
| width2 =
| tradename =
| legal_CA = Schedule I
| legal_DE = NpSG
| legal_UK = Class B
| legal_status =
| routes_of_administration = By mouth
| class = Empathogen–entactogen; Stimulant
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 152623-93-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O72F3CP4O8
| ATC_prefix = None
| ATC_suffix =
| PubChem = 192599
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 167141
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 124055
| synonyms =
| IUPAC_name = 1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
| C = 11 | H = 15 | N = 1 | O = 1
| SMILES = O2c1cc(ccc1CC2)CC(N)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H15NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-3,7-8H,4-6,12H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VRNGXHJGMCJRSQ-UHFFFAOYSA-N
}}
6-(2-Aminopropyl)-2,3-dihydrobenzofuran (6-APDB, 4-Desoxy-MDA, EMA-3) is a stimulant and entactogen drug of the phenethylamine and amphetamine classes.{{cite journal | vauthors = Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE | title = Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine | journal = Journal of Medicinal Chemistry | volume = 36 | issue = 23 | pages = 3700–6 | date = November 1993 | pmid = 8246240 | doi = 10.1021/jm00075a027 }} It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene bridge. 5-APDB (3-Desoxy-MDA) is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 6-APDB, along with 5-APDB, was first synthesized by David E. Nichols in the early 1990s while investigating non-neurotoxic MDMA analogues.
Pharmacology
In animal drug discrimination studies, 6-APDB fully substitutes for MBDB and MMAI but not for amphetamine or LSD. In vitro, 6-APDB has been shown to inhibit the reuptake of serotonin, dopamine, and norepinephrine with IC50 values of 322 nM, 1,997 nM, and 980 nM, respectively. These values are very similar to those of MDA, but with those for the catecholamines slightly lower in comparison, perhaps more similarly to MDMA. Though 6-APDB does not substitute for amphetamine in rats at the doses used in referenced study, based on its in vitro profile it can be suggested that it may have amphetamine-like effects at higher doses. It also has activities at serotonin receptors.{{cite journal | vauthors = Rickli A, Kopf S, Hoener MC, Liechti ME | title = Pharmacological profile of novel psychoactive benzofurans | journal = Br J Pharmacol | volume = 172 | issue = 13 | pages = 3412–3425 | date = July 2015 | pmid = 25765500 | pmc = 4500375 | doi = 10.1111/bph.13128 | url = https://pmc.ncbi.nlm.nih.gov/articles/PMC4500375/pdf/bph0172-3412.pdf}}
In subsequent animal studies, 6-APDB produced robust hyperlocomotion and, in drug discrimination tests, fully substituted for MDMA, partially substituted for DOM and cocaine, and failed to substitute for methamphetamine.{{cite journal | vauthors = Dolan SB, Forster MJ, Gatch MB | title = Discriminative stimulus and locomotor effects of para-substituted and benzofuran analogs of amphetamine | journal = Drug Alcohol Depend | volume = 180 | issue = | pages = 39–45 | date = November 2017 | pmid = 28865391 | pmc = 6463889 | doi = 10.1016/j.drugalcdep.2017.07.041 | url = https://pmc.ncbi.nlm.nih.gov/articles/PMC6463889/pdf/nihms-1016834.pdf}}
Chemistry
=Analogues=
Society and culture
=Legal status=
==United Kingdom==
6-APDB is a class B drug in the United Kingdom since June 10, 2013. It is banned by a blanket law on benzofurans and related compounds.{{cite web | url = http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | title = The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | access-date = 2014-03-11 | author = UK Home Office | date = 2014-03-05 | publisher = UK Government | archive-date = 2014-12-04 | archive-url = https://web.archive.org/web/20141204041058/http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | url-status = live }}
References
{{Reflist}}
{{Entactogens}}
{{Psychedelics}}
{{Monoamine releasing agents}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}
Category:6-Benzofuranethanamines
Category:Psychedelic phenethylamines
Category:Serotonin-norepinephrine-dopamine releasing agents