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6-MBPB

From Wikipedia, the free encyclopedia

Pharmaceutical compound
6-MBPB
Clinical data
Other names6-MABB; 6-(2-Methylaminobutyl)benzofuran
Drug classSerotonin–norepinephrine–dopamine releasing agent;Entactogen
Identifiers
  • 1-(1-benzofuran-6-yl)-N-methylbutan-2-amine
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H17NO
Molar mass203.285 g·mol−1
3D model (JSmol)
  • CCC(CC1=CC2=C(C=C1)C=CO2)NC
  • InChI=1S/C13H17NO/c1-3-12(14-2)8-10-4-5-11-6-7-15-13(11)9-10/h4-7,9,12,14H,3,8H2,1-2H3
  • Key:LVDZDORQOMAGGH-UHFFFAOYSA-N

6-MBPB, also known as6-(2-methylaminobutyl)benzofuran (6-MABB), is amonoamine releasing agent (MRA) andentactogen-likedrug of theamphetamine,phenylisobutylamine, andbenzofuran families.[1][2][3][4][5] It is apositional isomer of5-MBPB (5-MABB).[1][2][3][4][5]

The drug appears to act as aserotonin–norepinephrine–dopamine releasing agent (SNDRA).[1][2] TheEC50Tooltip half-maximal effective concentration values for induction of monoamine release in rat brainsynaptosomes have been reported for the individualenantiomers of 6-MBPB.[2] In the case of (S)-6-MBPB, they were 54 nM forserotonin, 77 nM fornorepinephrine, and 41 nM fordopamine, whereas for (R)-6-MBPB, they were 172 nM for serotonin, 227 nM for norepinephrine, and inactive for dopamine.[2] Hence, (S)-6-MBPB is an SNDRA, whereas (R)-MBPB is aserotonin–norepinephrine releasing agent (SNRA).[2] The enantiomers showed a mixed profile of acting as full versuspartial releasers.[2] Unlike5-MAPB, it is a relatively weakserotonin5-HT1B receptoragonist.[6] 6-MBPB partially substituted forMDMA in animaldrug discrimination tests at lower doses and fully substituted for MDMA at the highest dose, suggesting that it has entactogen-like effects.[1][2][4]

Along with 5-MBPB, 6-MBPB waspatented byMatthew Baggott andTactogen in 2021.[5] It was first described in thescientific literature by 2022.[3][4] 6-MBPB, along with other drugs like 5-MBPB, is being investigated as a novel MDMA-like drug for potential therapeutic purposes in medicine.[1][2]

See also

[edit]

References

[edit]
  1. ^abcdeFantegrossi WE, Gannon BM (September 2024). "A "Furious" Effort to Develop Novel 3,4-Methylenedioxymethamphetamine-Like Therapeutics".J Pharmacol Exp Ther.391 (1):18–21.doi:10.1124/jpet.124.002183.PMID 39293859.
  2. ^abcdefghiJohnson CB, Walther D, Baggott MJ, Baker LE, Baumann MH (September 2024)."Novel Benzofuran Derivatives Induce Monoamine Release and Substitute for the Discriminative Stimulus Effects of 3,4-Methylenedioxymethamphetamine".J Pharmacol Exp Ther.391 (1):22–29.doi:10.1124/jpet.123.001837.PMC 11413916.PMID 38272669.
  3. ^abcJohnson C (10 November 2022)."Benzofuran Derivatives Substitute for the Discriminative Stimulus Effects of 3,4-Methylenedioxymethamphetamine (MDMA) in Male Sprague-Dawley Rats".ScholarWorks at WMU. Retrieved21 January 2025.
  4. ^abcdJohnson CB, Walther D, Matthew BJ, Baumann MH, Baker LE (February 2022).Poster 28: Benzofuran derivatives substitute for the discriminative stimulus effects of MDMA in male Sprague-Dawley rats(PDF). 14th Annual Behavior, Biology, and Chemistry [(BBC]): Translational Research in Addiction, San Antonio Texas, Embassy Landmark, 26-27 February 2022. p. 20.Stimulus substitution tests were conducted with (RS) 5-MAPB, (R)-5-MAPB, (S)-5-MAPB, (R)-5-MBPB, (S)-5-MBPB, (R)-6-MBPB, and (S)-6-MBPB. All substances produced full substitution for MDMA. In separate experiments, serotonin release and reuptake assays with rat synaptosomes indicated these substances are substrate releasers of serotonin with nanomolar potency; slightly higher potency was observed with the S-enantiomers. The benzofuran scaffold may allow development of substances that retain MDMA-like therapeutic effects while reducing toxicities associated with MDMA.
  5. ^abc"Advantageous benzofuran compositions for mental disorders or enhancement".Google Patents. 8 June 2021. Retrieved21 January 2025.
  6. ^US 20230150963, Matthew Baggott, "Advantageous benzofuran compositions for mental disorders or enhancement", published 2023 May 18, assigned toTactogen 

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