5-APDB
{{Short description|Chemical compound}}
{{Infobox drug
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| verifiedrevid = 477223997
| image = 3-desoxy-MDA.svg
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| pregnancy_category =
| routes_of_administration = Oral
| class =
| legal_BR = F2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}
| legal_CA = Schedule I
| legal_DE = NpSG
| legal_UK = Class B
| legal_status =
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| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 152624-03-8
| ATC_prefix = None
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = UI10BAJ8SH
| ATC_suffix =
| PubChem = 192601
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 167143
| synonyms =
| IUPAC_name = 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine
| C=11 | H=15 | N=1 | O=1
| SMILES = Cl.CC(N)Cc1cc2CCOc2cc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H15NO.ClH/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11;/h2-3,7-8H,4-6,12H2,1H3;1H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BZKLFXQUBIRXAK-UHFFFAOYSA-N
}}
5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative 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 = 3700–3706 | date = November 1993 | pmid = 8246240 | doi = 10.1021/jm00075a027 }} It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge. 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead. 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDMA.
Pharmacology
In animal drug discrimination studies, 5-APDB's effects generalize most closely to non-stimulant MDMA analogues such as MBDB and MMAI, while producing no substitution for LSD or amphetamine. In vitro studies show that 5-APDB acts as a highly selective serotonin releasing agent (SSRA), with IC50 values of 130 nM, 7,089 nM, and 3,238 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively. 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}}
Chemistry
=Analogues=
In contrast to 5-APDB, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.
Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM in animal tests, although they were around one tenth as potent as DOM.{{cite journal | vauthors = Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM | title = Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats | journal = Journal of Medicinal Chemistry | volume = 29 | issue = 2 | pages = 302–304 | date = February 1986 | pmid = 3950910 | doi = 10.1021/jm00152a022 }}{{cite journal | vauthors = Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM | title = 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines | journal = Journal of Medicinal Chemistry | volume = 34 | issue = 1 | pages = 276–281 | date = January 1991 | pmid = 1992127 | doi = 10.1021/jm00105a043 }}
Society and culture
=Legal status=
==China==
As of October 2015 5-APDB is a controlled substance in China.{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | trans-title = Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances" | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}
==United Kingdom==
On June 10, 2013, 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.{{cite web | url = https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | title = Temporary class drug order report on 5-6APB and NBOMe compounds | access-date = 2013-06-13 | date = 4 Jun 2013 | publisher = UK Home Office | archive-date = 2017-08-24 | archive-url = https://web.archive.org/web/20170824221356/https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | url-status = live }} This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.{{cite news | title = 'NBOMe' and 'Benzofury' banned | date = 4 Jun 2013 | url = https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned | work = UK Home Office | access-date = 2013-06-13 | archive-date = 2013-09-21 | archive-url = https://web.archive.org/web/20130921060922/https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned | url-status = live }}
References
{{Reflist}}
{{Entactogens}}
{{Psychedelics}}
{{Monoamine releasing agents}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}
{{DEFAULTSORT:Aminopropyl)-2, 3-dihydrobenzofuran, 5-(2-}}
Category:5-Benzofuranethanamines
Category:Psychedelic phenethylamines
Category:Serotonin receptor modulators