5-MAPDB
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = 1-(2,3-dihydrobenzofuran-5-yl)-N-methylpropan-2-amine
| image = 5-MAPDB_structure.png
| width = 240
| legal_AU = Analogue of MDMA
| 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_US = analogue
| legal_US_comment = (MDMA)
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| CAS_number = 1354631-78-9
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| PubChem = 112500533
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| UNII = FS5Z21939Z
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| ChemSpiderID = 52085108
| chemical_formula = | C=12 | H=17 | N=1 | O=1
| smiles = CC(NC)CC1=CC(CCO2)=C2C=C1
| StdInChI = 1S/C12H17NO/c1-9(13-2)7-10-3-4-12-11(8-10)5-6-14-12/h3-4,8-9,13H,5-7H2,1-2H3
| StdInChIKey = PLQTZOCLUHHCOI-UHFFFAOYSA-N
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5-MAPDB (1-(2,3-dihydrobenzofuran-5-yl)-N-methylpropan-2-amine) is a chemical compound which acts as an entactogenic drug. It is structurally related to drugs like 5-APDB and 5-MAPB, which have similar effects to MDMA and have been used as recreational drugs. 5-MAPDB has been studied to determine its pharmacological activity, and was found to be a relatively selective serotonin releaser, though with weaker actions as a releaser of other monoamines and 5-HT2 receptor family agonist,{{cite journal | vauthors = Rickli A, Kopf S, Hoener MC, Liechti ME | title = Pharmacological profile of novel psychoactive benzofurans | journal = British Journal of Pharmacology | volume = 172 | issue = 13 | pages = 3412–25 | date = July 2015 | pmid = 25765500 | pmc = 4500375 | doi = 10.1111/bph.13128 }} similar to older compounds such as 5-APDB.{{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 = 3700–6 | date = November 1993 | pmid = 8246240 | doi = 10.1021/jm00075a027 }}
Legality
5-MAPDB was banned in the UK in June 2013 as a temporary class drug along with 9 other related compounds, despite having never been sold as a street drug itself. This was due to concerns that it would have similar effects to drugs such as 5-APB that had been widely sold already, and 5-MAPDB might therefore be likely to become used recreationally also, if it were not banned preemptively.{{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 = 2013-07-11 | date = 4 Jun 2013 | publisher = UK Home Office}}
See also
References
{{Reflist}}
{{Entactogens|state=expanded}}
{{Serotonergics}}
{{Phenethylamines}}