BK-5-MAPB

βk-5-MAPB, or BK-5-MAPB, is an entactogen of the benzofuran and cathinone groups which is related to both 5-MAPB and methylone. It was patented by Matthew Baggott and Tactogen and is under investigation by Tactogen for potential medical use.^[1]^[2]^[3]^[4]

Other namesBK-5-MAPB

Routes of
administrationOral

Drug classSerotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT_1B receptor agonist; Entactogen; Stimulant

CAS Number

2855950-94-4^Y

Quick facts Clinical data, Other names ...

BK-5-MAPB
Clinical data

Other names	BK-5-MAPB
Routes of administration	Oral
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT_1B receptor agonist; Entactogen; Stimulant
Identifiers
IUPAC name 1-(1-benzofuran-5-yl)-2-(methylamino)propan-1-one
CAS Number	2855950-94-4^Y
PubChem CID	163585306
ChemSpider	129866921
ChEMBL	ChEMBL5397369
Chemical and physical data
Formula	C₁₂H₁₃NO₂
Molar mass	203.241 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CC2=C(C=C1)OC=C2)NC
InChI InChI=1S/C12H13NO2/c1-8(13-2)12(14)10-3-4-11-9(7-10)5-6-15-11/h3-8,13H,1-2H3 Key:GKZGRACLZFHCFE-UHFFFAOYSA-N

Pharmacology

Pharmacodynamics

βk-5-MAPB acts as a monoamine releaser with selectivity for serotonin and has a similar potency to MDMA.^[1]^[2]^[5]^[3]^[6] In terms of monoamine release, (S)-βk-5-MAPB has shown a DATTooltip dopamine transporter/SERTTooltip serotonin transporter ratio of 0.6 and a DAT/NETTooltip norepinephrine transporter ratio of 2.7, while (R)-βk-5-MAPB has shown a DAT/SERT ratio of 18 and a DAT/NET ratio of 1.9.^[3] In addition, βk-5-MAPB, unlike MDMA, is a potent serotonin 5-HT_1B receptor agonist.^[7]

In rodent drug discrimination tests, (S)-βk-5-MAPB fully substitutes for MDMA whereas (R)-βk-5-MAPB partially substitutes for MDMA and dextroamphetamine at different doses, (R)-βk-5-MAPB and (S)-βk-5-MAPB both generalize to dextroamphetamine, and (S)-βk-5-MAPB but not (R)-βk-5-MAPB substitutes for DOM.^[4] Hence, (S)-βk-5-MAPB shows entactogen-, psychedelic-, and stimulant-like effects, whereas (R)-βk-5-MAPB shows more stimulant-like effects, some entactogen-like effects, and no psychedelic-like effects.^[4] In other tests, both (S)-βk-5-MAPB and (R)-βk-5-MAPB showed stimulant-like pro-impulsive effects, but (S)-βk-5-MAPB was more potent than (R)-βk-5-MAPB.^[8]

References

[1]
WO 2021/252538, Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", published 16 December 2021, assigned to Tactogen Inc.
[2]
WO 2023/107653, Baggott MJ, Lofthus SJ, De Leona XM, Singh A, Hudgins CJ, "Benzofuran salt morphic forms and mixtures for the treatment of mental disorders or mental enhancement", published 21 September 2023, assigned to Tactogen Inc.
[3]
Johnson C, Burroughs R, Walther D, Baggott M, Baumann M, Baker L (June 2023). Behavioral Assessments and Neurochemical Assays Differentiate the Effects of 1-(1-Benzofuran-5-yl)-2-(methylamino) propan-1-one Hydrochloride (BK-5-MAPB) Enantiomers (PDF). June 17-21, 2023: 85th CPDD Scientific Meeting, Denver, CO. Results: S-BK-5-MAPB produced dose-dependent increases in MDMA-lever responses and full substitution at 0.64 and 1.27 mg/kg; R-BK-5-MAPB produced less than 30% MDMA-lever responding. Both enantiomers increased distance traveled in a dose-dependent manner that was statistically significant compared to saline-treated controls (P= 0.0001). Both enantiomers were substrate-type releasers at all three transporters. The S-enantiomer displayed an MDMA-like profile with greater potency at SERT than DAT (DAT/SERT ratio of 0.6), while R-BK-5-MAPB had a typical stimulant profile (DAT/SERT ratio of 18). Both enantiomers had higher potency at DAT than NET (DAT/NET ratios of 2.7 and 1.9 for the S- and R-enantiomer, respectively). [...] Because they have reduced potency at NET, these novel substances may have utility in elucidating the contributions of NET to MDMA-like and typical stimulant effects.
[4]
Burroughs RL, Baggott MJ, Baker LE (March 2024). Enantiomers of a novel benzofuran have distinct discriminative stimulus effects (Poster 18) (PDF). 16th Annual Behavior, Biology, and Chemistry (BBC): Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024.
[5]
WO 2023/107715, Baggott M, Dalziel S, "Specialized combinations for mental disorders or mental enhancement", published 15 June 2023, assigned to Tactogen Inc.
[6]
Johnson C, Burroughs R, Walther D, Baggott M, Baumann M, Baker L (2024). "Behavioral Assessments and Neurochemical Assays Differentiate the Effects of 1-(1-Benzofuran-5-yl)-2-(methylamino) propan-1-one Hydrochloride (BK-5-MAPB) Enantiomers". Drug and Alcohol Dependence. 260 110018. doi:10.1016/j.drugalcdep.2023.110018.
[7]
US 20230150963, Matthew Baggott, "Advantageous benzofuran compositions for mental disorders or enhancement", published 2023 May 18, assigned to Tactogen
[8]
Steck KA, Brabant PD, Baggott MJ, Baker LE (March 2024). Proimpulsive effects of acute treatment with 1-(1-benzofuran-5-yl)-2-(methylamino) propan1-one hydrochloride (BK-5-MAPB) enantiomers in rats (Poster 86) (PDF). 16th Annual Behavior, Biology, and Chemistry (BBC): Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024.

Pharmacology

Pharmacodynamics

See also

References

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