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,[2] similar to older compounds such as 5-APDB.[3]

5-MAPDB
Legal status
Legal status
Identifiers
  • 1-(2,3-dihydrobenzofuran-5-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO
Molar mass191.274 g·mol−1
3D model (JSmol)
  • CC(NC)CC1=CC(CCO2)=C2C=C1
  • InChI=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
  • Key:PLQTZOCLUHHCOI-UHFFFAOYSA-N

Legality

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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.[4]

See also

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References

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  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. ^ Rickli A, Kopf S, Hoener MC, Liechti ME (July 2015). "Pharmacological profile of novel psychoactive benzofurans". British Journal of Pharmacology. 172 (13): 3412–25. doi:10.1111/bph.13128. PMC 4500375. PMID 25765500.3412-25&rft.date=2015-07&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4500375#id-name=PMC&rft_id=info:pmid/25765500&rft_id=info:doi/10.1111/bph.13128&rft.aulast=Rickli&rft.aufirst=A&rft.au=Kopf, S&rft.au=Hoener, MC&rft.au=Liechti, ME&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4500375&rfr_id=info:sid/en.wikipedia.org:5-MAPDB" class="Z3988">
  3. ^ 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): 3700–6. doi:10.1021/jm00075a027. PMID 8246240.3700-6&rft.date=1993-11&rft_id=info:doi/10.1021/jm00075a027&rft_id=info:pmid/8246240&rft.aulast=Monte&rft.aufirst=AP&rft.au=Marona-Lewicka, D&rft.au=Cozzi, NV&rft.au=Nichols, DE&rfr_id=info:sid/en.wikipedia.org:5-MAPDB" class="Z3988">
  4. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-07-11.