5-MAPBT

5-MAPBT
Clinical data
Other names	5-(2-(Methylamino)propyl)-1-benzothiophene; MY400; MY-400
Drug class	Monoamine releasing agent; Serotonin 5-HT1B receptor agonist; Entactogen
ATC code	None;
Identifiers
	IUPAC name 1-(1-benzothiophen-5-yl)-N-methylpropan-2-amine;
CAS Number	2613382-32-2 ;
PubChem CID	165889699;
ChemSpider	103843875;
Chemical and physical data
Formula	C12H15NS
Molar mass	205.32 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC2=C(C=C1)SC=C2)NC;
	InChI InChI=1S/C12H15NS/c1-9(13-2)7-10-3-4-12-11(8-10)5-6-14-12/h3-6,8-9,13H,7H2,1-2H3; Key:SKSFWFUEBKJIAJ-UHFFFAOYSA-N;

5-MAPBT, also known as 5-(2-(methylamino)propyl)-1-benzothiophene, is a possible entactogen of the phenethylamine, amphetamine, and benzothiophene families.^[2]^[3] ^[4] It is closely related to 5-MAPB, but with the oxygen atom replaced by sulfur, changing the core ring structure to benzothiophene rather than benzofuran.^[4]

The drug acts as a potent monoamine releasing agent, including of serotonin and dopamine, and as a potent serotonin 5-HT_1B receptor agonist and serotonin 5-HT_2B receptor antagonist.^[4] It is also a monoamine oxidase A (MAO-A) inhibitor, with an IC₅₀Tooltip half-maximal inhibitory concentration of 765 nM.^[4]

It produces anxiolytic-like and antiobsessional-like effects in the marble burying test in rodents.^[4] However, benzothiophenes like 5-MAPBT, despite their induction of dopamine release, are said to lack hyperlocomotion or stimulant-like effects in rodents.^[3]^[5]

5-MAPBT has been studied and patented by Matthew J. Baggott at Tactogen.^[4] The drug has also been patented by Mydecine and given the developmental code name MY400.^[6]

References

^ Mydecine (5 January 2024). "Novel short-acting psychoactive compounds of the mdma class". Google Patents. Retrieved 23 October 2024.
^ Halford, Bethany (16 June 2025). "Drug companies are investing big in psychedelics, but can they engineer out the trip?". Chemical & Engineering News. 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.
^ ^a ^b Moosmann B, Niendorf LM (2022). "Analytica 2022 conference report on toxicological and forensic chemistry". 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.
^ ^a ^b ^c ^d ^e ^f WO 2022/010937, Baggott M, "Advantageous benzothiophene compositions for mental disorders or enhancement.", published 13 January 2022, assigned to Tactogen Inc.
^ Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, Kavanagh PV, Dowling G, Holy M, Jaentsch K, Walther D, Brandt SD, Stockner T, Baumann MH, Halberstadt AL, Sitte HH (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.
^ "Novel short-acting psychoactive compounds of the mdma class". Google Patents. 5 January 2024. Retrieved 1 November 2025.

External links

5-MAPBT - Isomer Design

[US20240197679A1-1] Mydecine (5 January 2024). "Novel short-acting psychoactive compounds of the mdma class". Google Patents. Retrieved 23 October 2024.

[Halford2025-2] Halford, Bethany (16 June 2025). "Drug companies are investing big in psychedelics, but can they engineer out the trip?". Chemical & Engineering News. 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.

[MoosmannNiendorf2022-3] Moosmann B, Niendorf LM (2022). "Analytica 2022 conference report on toxicological and forensic chemistry". 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.

[WO2022010937A1-4] ^ ^a ^b ^c ^d ^e ^f WO 2022/010937, Baggott M, "Advantageous benzothiophene compositions for mental disorders or enhancement.", published 13 January 2022, assigned to Tactogen Inc.

[RudinMcCorvyGlatfelter2022-5] Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, Kavanagh PV, Dowling G, Holy M, Jaentsch K, Walther D, Brandt SD, Stockner T, Baumann MH, Halberstadt AL, Sitte HH (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.

[US20240197679-6] "Novel short-acting psychoactive compounds of the mdma class". Google Patents. 5 January 2024. Retrieved 1 November 2025.

[1]

[2]

[3]

[4]

[5]

[6]

See also

References

External links