5-MAPB has been described by Matthew Baggott as the MDMA analogue so far known that has the closest effects and so-called "magic" to MDMA itself.[8][9] Other analogues that lack the full quality of MDMA includeMBDB,methylone,6-APDB,5-APDB,6-APB,5-APB,MDAT, andMDAI, among others.[8][9]
Little formal knowledge exists on 5-MAPB. It does not form theα-methyldopamine metabolite that contributes to theneurotoxicity ofMDMA orMDA.[11][12][13][14] A study in rats indicated that the major metabolites of 5-MAPB are5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[15]
5-MAPB is not listed itself in the CDSA but since it is structurally related toMDMA it may be considered illegal in Canada, although this has not been tested in court.[16]
5-MAPB was originally banned in the UK in June 2013 under aTemporary class drug order.[20] On March 5, 2014, the UK Home Office announced that 5-MAPB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.[21]
^abcWO 2021/252538, Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", published 16 December 2021, assigned to Tactogen Inc.
^abRoque Bravo R, Silva JP, Carmo H, Carvalho F, Dias da Silva D (2022). "The Toll of Benzofurans in the Context of Drug Abuse".Handbook of Substance Misuse and Addictions. Cham: Springer International Publishing. p. 1–24.doi:10.1007/978-3-030-67928-6_168-1.ISBN978-3-030-67928-6.
^Shimshoni JA, Winkler I, Golan E, Nutt D (January 2017). "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues".Naunyn Schmiedebergs Arch Pharmacol.390 (1):15–24.doi:10.1007/s00210-016-1297-4.hdl:10044/1/43622.PMID27650729.
^abJohnson CB, Burroughs RL, Baggott MJ, Davidson CJ, Perrine SA, Baker LE (2022).314.03 / RR6 - Locomotor stimulant effects and persistent serotonin depletions following [1-Benzofuran-5-yl)-N-methylpropan-2-amine (5-MAPB) treatment in Sprague-Dawley rats. Society for Neuroscience Conference, Nov. 14, 2022, San Diego, CA.5-MAPB has been marketed as a less neurotoxic analogue of MDMA, but no studies have addressed whether 5-MAPB can cause the long lasting serotonergic changes seen with high or repeated MDMA dosing. [...] Neurochemical analyses indicated a statistically significant reduction in 5‑HT and 5-HIAA in all brain regions assessed 24 hours and two weeks after 6 mg/kg 5‑MAPB, with no statistically significant differences in monoamine levels between 1.2 mg/kg and saline-treated rats. There were also non-significant trends for reductions in striatal dopamine at both time intervals after 6 mg/kg 5-MAPB. These results show that 5-MAPB can dose-dependently produce persistent changes in 5-HT and 5-HIAA that appear analogous to those produced by MDMA.
^Shimshoni JA, Winkler I, Golan E, Nutt D (January 2017). "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues".Naunyn-Schmiedeberg's Archives of Pharmacology.390 (1):15–24.doi:10.1007/s00210-016-1297-4.hdl:10044/1/43622.PMID27650729.
^Miller RT, Lau SS, Monks TJ (April 1997). "2,5-Bis-(glutathion-S-yl)-alpha-methyldopamine, a putative metabolite of (+/-)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations".European Journal of Pharmacology.323 (2–3):173–180.doi:10.1016/S0014-2999(97)00044-7.PMID9128836.
^Conway EL, Louis WJ, Jarrott B (December 1978). "Acute and chronic administration of alpha-methyldopa: regional levels of endogenous and alpha-methylated catecholamines in rat brain".European Journal of Pharmacology.52 (3–4):271–280.doi:10.1016/0014-2999(78)90279-0.PMID729639.
^Welter J, Kavanagh P, Meyer MR, Maurer HH (February 2015). "Benzofuran analogues of amphetamine and methamphetamine: studies on the metabolism and toxicological analysis of 5-APB and 5-MAPB in urine and plasma using GC-MS and LC-(HR)-MS(n) techniques".Analytical and Bioanalytical Chemistry.407 (5):1371–1388.doi:10.1007/s00216-014-8360-0.PMID25471293.S2CID20653012.
^"Schedule I". Government Of Canada. 2014-12-12. Archived fromthe original on 2013-11-22. Retrieved2014-12-13.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
