Chemistry:5-APDB
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| Routes of administration | Oral |
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| Formula | C11H15NO |
| Molar mass | 177.247 g·mol−1 |
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5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug of the phenethylamine and amphetamine classes.[1] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[1] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[1] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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.[1]
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.[1] 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.[1] In contrast, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.[1]
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.[2][3]
Legal status
China
As of October 2015 5-APDB is a controlled substance in China.[4]
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.[5] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[6]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry 36 (23): 3700–3706. November 1993. doi:10.1021/jm00075a027. PMID 8246240.
- ↑ "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. February 1986. doi:10.1021/jm00152a022. PMID 3950910.
- ↑ "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry 34 (1): 276–281. January 1991. doi:10.1021/jm00105a043. PMID 1992127.
- ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.
- ↑ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds.
- ↑ "'NBOMe' and 'Benzofury' banned". UK Home Office. 4 Jun 2013. https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned.
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