BK-5-MAPB
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = 1-(1-benzofuran-5-yl)-2-(methylamino)propan-1-one
| image = Bk5MAPB_structure.png
| width = 240px
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| class = Serotonin–norepinephrine–dopamine releasing agent; Entactogen; Stimulant
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2855950-94-4
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| PubChem = 163585306
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| synonyms = BK-5-MAPB
| C=12 | H=13 | N=1 | O=2
| SMILES = CC(C(=O)C1=CC2=C(C=C1)OC=C2)NC
| StdInChI = 1S/C12H13NO2/c1-8(13-2)12(14)10-3-4-11-9(7-10)5-6-15-11/h3-8,13H,1-2H3
| StdInChIKey = GKZGRACLZFHCFE-UHFFFAOYSA-N
}}
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.
Pharmacology
It acts as a monoamine releaser with selectivity for serotonin and has a similar potency to MDMA.{{cite patent | country = WO | number = 2021/252538 | title = Advantageous benzofuran compositions for mental disorders or enhancement | inventor = Baggott M | assign = Tactogen Inc. | pubdate = 16 December 2021 | url = https://patents.google.com/patent/WO2021252538A2/en?oq=WO2021252538 }}{{cite patent | country = WO | number = 2023/107653 | title = Benzofuran salt morphic forms and mixtures for the treatment of mental disorders or mental enhancement | pubdate = 21 September 2023 | inventor = Baggott MJ, Lofthus SJ, De Leona XM, Singh A, Hudgins CJ | assign = Tactogen Inc. | url = https://patents.google.com/patent/WO2023107653A2/en?oq=WO2023107653 }}{{cite patent | country = WO | number = 2023/107715 | title = Specialized combinations for mental disorders or mental enhancement | inventor = Baggott M, Dalziel S | assign = Tactogen Inc. | url = https://patents.google.com/patent/WO2023107715A1/en?oq=WO2023%2f107715 | pubdate = 15 June 2023 }}{{cite conference | vauthors = Johnson C, Burroughs R, Walther D, Baggott M, Baumann M, Baker L | title = Behavioral Assessments and Neurochemical Assays Differentiate the Effects of 1-(1-Benzofuran-5-yl)-2-(methylamino) propan-1-one Hydrochloride (BK-5-MAPB) Enantiomers | conference = June 17-21, 2023: 85th CPDD Scientific Meeting, Denver, CO | date = June 2023 | url = https://cpdd.org/wp-content/uploads/2023/07/Oral_Communications_Abstract_Book_Final.pdf#page=27 | conference-url = https://cpdd.org/meetings/past-meeting-recaps/ | quote = 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.}}{{cite journal | vauthors = Johnson C, Burroughs R, Walther D, Baggott M, Baumann M, Baker L | title=Behavioral Assessments and Neurochemical Assays Differentiate the Effects of 1-(1-Benzofuran-5-yl)-2-(methylamino) propan-1-one Hydrochloride (BK-5-MAPB) Enantiomers | journal=Drug and Alcohol Dependence | volume=260 | date=2024 | doi=10.1016/j.drugalcdep.2023.110018 | page=110018 }} In terms of monoamine release, (S)-βk-5-MAPB has shown a {{Abbrlink|DAT|dopamine transporter}}/{{Abbrlink|SERT|serotonin transporter}} ratio of 0.6 and a {{Abbr|DAT|dopamine transporter}}/{{Abbrlink|NET|norepinephrine transporter}} ratio of 2.7, while (R)-βk-5-MAPB has shown a {{Abbr|DAT|dopamine transporter}}/{{Abbr|SERT|serotonin transporter}} ratio of 18 and a {{Abbr|DAT|dopamine transporter}}/{{Abbr|NET|norepinephrine transporter}} ratio of 1.9.
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.{{cite conference | vauthors = Burroughs RL, Baggott MJ, Baker LE | title = Enantiomers of a novel benzofuran have distinct discriminative stimulus effects (Poster 18) | conference = 16th Annual Behavior, Biology, and Chemistry (BBC): Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024 | date = March 2024 | url = https://ww2.uthscsa.edu/ARTT/BBC/print/2024Program.pdf#page=20 }} 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. 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.{{cite conference | vauthors = Steck KA, Brabant PD, Baggott MJ, Baker LE | title = Proimpulsive effects of acute treatment with 1-(1-benzofuran-5-yl)-2-(methylamino) propan1-one hydrochloride (BK-5-MAPB) enantiomers in rats (Poster 86) | conference = 16th Annual Behavior, Biology, and Chemistry (BBC): Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024 | date = March 2024 | url = https://ww2.uthscsa.edu/ARTT/BBC/print/2024Program.pdf#page=37 }}
References
{{Reflist}}
{{Entactogens}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
Category:5-Benzofuranethanamines