6-MBPB

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
PubChem CID
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 as 6-(2-methylaminobutyl)benzofuran (6-MABB), is a monoamine releasing agent (MRA) and entactogen-like drug of the amphetamine, phenylisobutylamine, and benzofuran families. It is a positional isomer of 5-MBPB (5-MABB).

The drug appears to act as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). The EC50Tooltip half-maximal effective concentration values for induction of monoamine release in rat brain synaptosomes have been reported for the individual enantiomers of 6-MBPB. In the case of (S)-6-MBPB, they were 54 nM for serotonin, 77 nM for norepinephrine, and 41 nM for dopamine, whereas for (R)-6-MBPB, they were 172 nM for serotonin, 227 nM for norepinephrine, and inactive for dopamine. Hence, (S)-6-MBPB is an SNDRA, whereas (R)-MBPB is a serotonin–norepinephrine releasing agent (SNRA). The enantiomers showed a mixed profile of acting as full versus partial releasers. Unlike 5-MAPB, it is a relatively weak serotonin 5-HT1B receptor agonist. 6-MBPB partially substituted for MDMA in animal drug discrimination tests at lower doses and fully substituted for MDMA at the highest dose, suggesting that it has entactogen-like effects.

Along with 5-MBPB, 6-MBPB was patented by Matthew Baggott and Tactogen in 2021. It was first described in the scientific literature by 2022. 6-MBPB, along with other drugs like 5-MBPB, is being investigated as a novel MDMA-like drug for potential therapeutic purposes in medicine.

See also

References

  1. 1 2 3 4 5 Fantegrossi 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. 1 2 3 4 5 6 7 8 9 Johnson 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. 1 2 3 Johnson 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. Retrieved 21 January 2025.
  4. 1 2 3 4 Johnson 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. 1 2 3 "Advantageous benzofuran compositions for mental disorders or enhancement". Google Patents. 8 June 2021. Retrieved 21 January 2025.
  6. ↑ US 20230150963, Matthew Baggott, "Advantageous benzofuran compositions for mental disorders or enhancement", published 2023 May 18, assigned to Tactogen