6-MAPBT

Last updated

6-MAPBT
6-MAPBT.svg
Clinical data
Other names6-(2-(Methylamino)propyl)-1-benzothiophene; MY300; MY-300
Drug class Monoamine releasing agent; Serotonin 5-HT1B receptor agonist; Entactogen
ATC code
  • None
Identifiers
  • 1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine
PubChem CID
Chemical and physical data
Formula C12H15NS
Molar mass 205.32 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)C=CS2)NC
  • InChI=1S/C12H15NS/c1-9(13-2)7-10-3-4-11-5-6-14-12(11)8-10/h3-6,8-9,13H,7H2,1-2H3
  • Key:ZTCVZGKXXWDMJJ-UHFFFAOYSA-N

6-MAPBT, also known as 6-(2-(methylamino)propyl)-1-benzothiophene, is a possible entactogen of the phenethylamine, amphetamine, and benzothiophene families related to MDMA. [1] [2] [3]

Contents

It acts as a monoamine releasing agent and serotonin receptor modulator. [3] The drug's EC50 Tooltip half-maximal effective concentration values for monoamine release are 57 nM for serotonin and 71 nM for dopamine. [3] It is also a potent agonist of the serotonin 5-HT1B receptor, with an EC50 of 24 nM, and is a potent antagonist of the serotonin 5-HT2B receptor, with an IC50 Tooltip half-maximal inhibitory concentration of 72 nM. [3] Conversely, it is far weaker as an agonist of the serotonin 5-HT2A receptor (EC50 = 959 nM) and is inactive at the serotonin 5-HT1A receptor. [3] In addition to the preceding actions, the drug is a monoamine oxidase A (MAO-A) inhibitor, with an IC50 of 945 nM. [3]

It produces anxiolytic-like and antiobsessional-like effects in the marble burying test in rodents. [3] However, benzothiophenes like 6-MAPBT, despite their induction of dopamine release, are said to lack hyperlocomotion or stimulant-like effects in rodents. [2] [4]

6-MAPBT has been studied and patented by Matthew J. Baggott at Tactogen. [1] [3] The drug has also been patented by Mydecine and given the developmental code name MY300. [5]

See also

References

  1. 1 2 Halford B (16 June 2025). "Drug companies are investing big in psychedelics, but can they engineer out the trip?". Chemical & Engineering News. 100 (9): 28. Retrieved 1 November 2025. What Tactogen is trying to do, Baggott says, is make novel molecules that share MDMA's core therapeutic effects but have fewer undesirable effects, such as acute hypertension, overuse liability, and decreased therapeutic effects with repeated use. "We're trying to make molecules that engineer away some of those things," he says. To accomplish that, Tactogen scientists use machine learning to model how changes to MDMA's structure might affect the drug's biochemistry. They synthesize the molecules that seem most interesting, such as 5-MAPBT and 6-MAPBT, test them in assays, and then feed that information back into their machine learning system.
  2. 1 2 Moosmann B, Niendorf LM (7 October 2022). "Analytica 2022 conference report on toxicological and forensic chemistry". Lab Automation News. Using (2-aminopropyl)benzo[b]thiophene analogs (APBTs) as a representative example and moving from synthesis to pharmacological evaluation Prof. Brandt discussed that the differentiation between various NPS isomers can be a challenge. APBT isomers, e.g., 5-MAPBT, 6-MAPBT, and many others are new monoamine transporter ligands that are similar to MDMA in both its structure and effects and bind to the 5-HT2A receptor subtype. He pointed out that despite having shown activity in vitro, they interestingly, and above all unexpectedly, lack stimulant effects as APBT isomers failed to trigger locomotor activity in mice. This suggests psychedelic and entactogenic effects combined with a low abuse potential, which, in turn, could be used as a therapeutic approach in drug-assisted psychotherapy and is worth investigating further.
  3. 1 2 3 4 5 6 7 8 WO 2022010937A1,Baggott M,"Advantageous benzothiophene compositions for mental disorders or enhancement",published 13 January 2022, assigned to Tactogen Inc.
  4. ↑ Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, et al. (March 2022). "(2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice". Neuropsychopharmacology. 47 (4): 914–923. doi:10.1038/s41386-021-01221-0. PMC   8882185 . PMID   34750565.
  5. ↑ US 20240197679,Hoyer DW, Roscow RF, Ling R, Gao C,"Novel short-acting psychoactive compounds of the MDMA class",published 20 June 2024, assigned to Mydecine Innovations Group Inc.
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