5-APDB explained
| Verifiedfields: | changed |
| Watchedfields: | changed |
| Verifiedrevid: | 477223997 |
| Iupac Name: | 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine |
| Legal Br: | F2 |
| Legal Br Comment: | [1] |
| Legal Ca: | Schedule I |
| Legal De: | NpSG |
| Legal Uk: | Class B |
| Routes Of Administration: | Oral |
| Cas Number: | 152624-03-8 |
| Atc Prefix: | none |
| Unii: | UI10BAJ8SH |
| Pubchem: | 192601 |
| Chemspiderid: | 167143 |
| C: | 11 |
| H: | 15 |
| N: | 1 |
| O: | 1 |
| Smiles: | Cl.CC(N)Cc1cc2CCOc2cc1 |
| 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: | 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classes.[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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]
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]
Legal status
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]
Notes and References
- Web site: Anvisa . Brazilian Health Regulatory Agency . 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. live . 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 . 2023-08-27 . 2023-08-27 . . pt-BR . 2023-07-25.
- Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE . 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 . 8246240 . 10.1021/jm00075a027 .
- Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM . 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 . 3950910 . 10.1021/jm00152a022 .
- Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM . 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines . Journal of Medicinal Chemistry . 34 . 1 . 276–281 . January 1991 . 1992127 . 10.1021/jm00105a043 .
- Web site: 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" . China Food and Drug Administration . 27 September 2015 . zh . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . 1 October 2015 . dead .
- Web site: Temporary class drug order report on 5-6APB and NBOMe compounds . 2013-06-13 . 4 Jun 2013 . UK Home Office . 2017-08-24 . https://web.archive.org/web/20170824221356/https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds . live .
- News: 'NBOMe' and 'Benzofury' banned . 4 Jun 2013 . UK Home Office . 2013-06-13 . 2013-09-21 . https://web.archive.org/web/20130921060922/https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned . live .
