5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, also known as 3-Desoxy-MDA or EMA-4) is a potential entactogenic substance belonging to the phenethylamine and amphetamine classes. It is derived from MDA, where a methylene bridge has replaced the oxygen atom at the 3-position of the 3,4-methylenedioxy ring. Another related compound is 6-APDB, which differs from 5-APDB by having a methylene bridge at the 4-position instead of an oxygen atom. The development of 5-APDB can be attributed to a research team led by David E. Nichols at Purdue University, with a focus on creating non-neurotoxic analogs of MDMA.
In animal studies, 5-APDB’s effects most closely resemble those of non-stimulant MDMA analogs like MBDB and MMAI without exhibiting similarities to LSD or amphetamine. In vitro experiments have revealed that 5-APDB functions as a highly selective serotonin-releasing agent (SSRA), with inhibition values of 130 nM, 7,089 nM, and 3,238 nM for serotonin, dopamine, and norepinephrine reuptake, respectively. On the other hand, 6-APDB has a more balanced influence on the three monoamine neurotransmitters and behaves more like MDA and MDMA.
Methoxy-substituted derivatives of 5-APDB and 6-APDB have also been synthesized and assessed in animal tests, where they substituted for DOM, although they demonstrated lower potency, roughly one-tenth that of DOM.
As of October 2015, 5-APDB has been categorized as a controlled substance in China.
On June 10, 2013, 5-APDB and several analogs were designated as Temporary Class Drugs in the United Kingdom, in line with a recommendation from the ACMD (Advisory Council on the Misuse of Drugs). This classification renders the sale and import of these specified substances illegal and subject to the same legal treatment as class B drugs.
1. What is 5-APDB?
5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB) is a putative entactogen drug that belongs to the phenethylamine and amphetamine classes. It is a structural analog of MDA (3,4-methylenedioxyamphetamine) with some modifications.
2. How is 5-APDB different from MDA and MDMA?
5-APDB is similar in structure to MDA but has a methylene bridge replacing the 3-position oxygen in the 3,4-methylenedioxy ring. This structural difference gives 5-APDB unique pharmacological properties compared to MDA and MDMA.
3. Who developed 5-APDB, and for what purpose?
5-APDB was developed by a research team led by David E. Nichols at Purdue University. Their goal was to create non-neurotoxic analogs of MDMA for scientific research.
4. What effects does 5-APDB produce in animal studies?
In animal studies, the effects of 5-APDB most closely resemble those of non-stimulant MDMA analogs like MBDB and MMAI. It doesn’t substitute for LSD or amphetamine in these studies.
5. How does 5-APDB affect neurotransmitters in the brain?
In vitro studies have shown that 5-APDB acts as a highly selective serotonin-releasing agent (SSRA). It has moderate effects on inhibiting the reuptake of serotonin, dopamine, and norepinephrine.
6. Is 5-APDB legally controlled in any country?
Yes, 5-APDB is a controlled substance in certain countries. For example, China categorized it as a controlled substance in October 2015. In the United Kingdom, 5-APDB was classified as a Temporary Class Drug in 2013, making its sale and import illegal.
7. Are there any analogs or derivatives of 5-APDB?
Yes, 6-APDB is an analog of 5-APDB, where the 4-position oxygen has been replaced by a methylene bridge instead.
8. Are there methoxy-substituted analogs of 5-APDB and 6-APDB?
Yes, methoxy-substituted analogs of 5-APDB and 6-APDB have been synthesized and tested in animal studies. They were found to substitute for DOM but were less potent, approximately one-tenth as complete.
Please note that 5-APDB and related substances are subject to legal restrictions in many places and should only be used for legitimate scientific research purposes.
- Anvisa (2023-07-24). “Resolution No. 804 by the Collegiate Board – Compilation of Substances under Special Control” [Official Gazette of the Union, 2023-07-25]. Retrieved on 2023-08-27. (Original source archived until 2023-08-27) – This is an official document from the Brazilian Health Regulatory Agency (Anvisa) regarding the classification of substances under special control.
- Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE (November 1993). “Development and Pharmacological Assessment of Benzofuran, Indan, and Tetralin Analogues of 3,4-(Methylenedioxy)amphetamine” published in the Journal of Medicinal Chemistry, Volume 36, Issue 23, Pages 3700-3706. DOI: 10.1021/jm00075a027. PMID: 8246240 – This research paper discusses the synthesis and pharmacological examination of analogues of a specific amphetamine derivative.
- Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM (February 1986). “Synthesis and Assessment of 2,3-Dihydrobenzofuran Analogues of the Hallucinogen 1-(2,5-Dimethoxy-4-Methylphenyl)-2-Aminopropane” published in the Journal of Medicinal Chemistry, Volume 29, Issue 2, Pages 302-304. DOI: 10.1021/jm00152a022. PMID: 3950910 – This paper focuses on the synthesis and evaluation of analogues of a hallucinogenic substance.
- Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). “2,3-Dihydrobenzofuran Analogues of Hallucinogenic Phenethylamines” published in the Journal of Medicinal Chemistry, Volume 34, Issue 1, Pages 276-281. DOI: 10.1021/jm00105a043. PMID: 1992127 – This research discusses analogues of hallucinogenic phenethylamines.
- “Notice on Printing and Distributing the ‘Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances'” (in Chinese). Issued by the China Food and Drug Administration on 27 September 2015. Retrieved on 1 October 2015. (Original source archived until 1 October 2015) – This is an official notice from the China Food and Drug Administration regarding the scheduling of non-pharmaceutical narcotic drugs and psychotropic substances.
- “Report on the Temporary Classification of 5-6APB and NBOMe Compounds” published by the UK Home Office on 4 June 2013. Retrieved on 2013-06-13 – This report discusses the temporary classification of specific compounds by the UK Home Office.
- “Ban on ‘NBOMe’ and ‘Benzofury'” announced by the UK Home Office on 4 June 2013. Retrieved on 2013-06-13 – This announcement pertains to the ban on substances known as ‘NBOMe’ and ‘Benzofury’ by the UK Home Office.