5-APDB

5-APDB

5-APDB

Chemical compound

5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug of the phenethylamine and amphetamine classes.[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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.[2]

Quick Facts Clinical data, Routes ofadministration ...

In animal 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.[2] 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.[2] In contrast, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.[2]

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.[3][4]

China

As of October 2015 5-APDB is a controlled substance in China.[5]

UK

On June 10, 2013, 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[6] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[7]

References

  1. [1]
    Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. [2]
    Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE (November 1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry. 36 (23): 3700–3706. doi:10.1021/jm00075a027. PMID 8246240.
  3. [3]
    Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM (February 1986). "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 of Medicinal Chemistry. 29 (2): 302–304. doi:10.1021/jm00152a022. PMID 3950910.
  4. [4]
    Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry. 34 (1): 276–281. doi:10.1021/jm00105a043. PMID 1992127.
  5. [5]
    "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  6. [6]
    "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13.
  7. [7]
    "'NBOMe' and 'Benzofury' banned". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13.
Share this article:

This article uses material from the Wikipedia article 5-APDB, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.