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 include MBDB, methylone, 6-APDB, 5-APDB, 6-APB, 5-APB, MDAT, and MDAI, among others.[8][9]
Little formal knowledge exists on 5-MAPB. It does not form the α-methyldopamine metabolite that contributes to the neurotoxicity of MDMA or MDA.[11][12][13][14] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[15]
Legal Status
Canada
5-MAPB is not listed itself in the CDSA but since it is structurally related to MDMA it may be considered illegal in Canada, although this has not been tested in court.[16]
China
As of October 2015 5-MAPB is a controlled substance in China.[17]
Luxembourg
As of July 2021, 5-MAPB is not cited in the list of prohibited substances.[18] Therefore, it is still a legal substance.
United Kingdom
5-MAPB was originally banned in the UK in June 2013 under a Temporary class drug order.[19] 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.[20]
^ 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.
^ abWO 2021/252538, Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", published 16 December 2021, assigned to Tactogen Inc.
^ 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 from the original on 2013-11-22. Retrieved 2014-12-13.
^"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 from the original on 1 October 2015. Retrieved 1 October 2015.
