5-MAPB explained

5-MAPB, also known as 5-(N-methyl-2-aminopropyl)benzofuran, is an entactogen and designer drug of the amphetamine family that is similar to MDMA in its structure and effects.[1]

Pharmacology

Pharmacodynamics

5-MAPB acts as a serotonin–norepinephrine–dopamine releasing agent with values for induction of monoamine release of 64nM for serotonin, 24nM for norepinephrine, and 41nM for dopamine.[2] [3] [4] [5] It is also a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[6]

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.[7] [8] 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.

5-MAPB has been marketed as a less- or non-neurotoxic alternative to MDMA.[9] However, 5-MAPB has been found to be a dose-dependent serotonergic neurotoxin in rodents similarly to MDMA, and might also be a dopaminergic neurotoxin.

Pharmacokinetics

Little formal knowledge exists on 5-MAPB. It does not form the α-methyldopamine metabolite that contributes to the neurotoxicity of MDMA or MDA.[10] [11] [12] [13] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[14]

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.[15]

China

As of October 2015 5-MAPB is a controlled substance in China.[16]

Luxembourg

As of July 2021, 5-MAPB is not cited in the list of prohibited substances.[17] 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.[18] 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.[19]

See also

Notes and References

  1. Web site: Temporary class drug order report on 5-6APB and NBOMe compounds . 2013-07-10 . 4 June 2013 . UK Home Office.
  2. Book: Roque Bravo, Rita . Silva . João Pedro . Carmo . Helena . Carvalho . Félix . Dias da Silva . Diana . Handbook of Substance Misuse and Addictions . The Toll of Benzofurans in the Context of Drug Abuse . Springer International Publishing . Cham . 2022 . 978-3-030-67928-6 . 10.1007/978-3-030-67928-6_168-1 . 1–24.
  3. Oeri HE . Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy . Journal of Psychopharmacology . 35 . 5 . 512–536 . May 2021 . 32909493 . 8155739 . 10.1177/0269881120920420 .
  4. Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH . The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats . Psychopharmacology (Berl) . 237 . 12 . 3703–3714 . December 2020 . 32875347 . 7686291 . 10.1007/s00213-020-05648-z .
  5. Sahai MA, Davidson C, Khelashvili G, Barrese V, Dutta N, Weinstein H, Opacka-Juffry J . Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances - The case of the benzofuran 5-MAPB . Progress in Neuro-Psychopharmacology & Biological Psychiatry . 75 . 1–9 . April 2017 . 27890676 . 10.1016/j.pnpbp.2016.11.004 . 30943496 .
  6. Shimshoni JA, Winkler I, Golan E, Nutt D . Neurochemical binding profiles of novel indole and benzofuran MDMA analogues . Naunyn Schmiedebergs Arch Pharmacol . 390 . 1 . 15–24 . January 2017 . 27650729 . 10.1007/s00210-016-1297-4 .
  7. Baggott M . Beyond Ecstasy: Progress in Developing and Understanding a Novel Class of Therapeutic Medicine . PS2023 [Psychedelic Science 2023, June 19-23, 2023, Denver, Colorado] . 23 June 2023 . Multidisciplinary Association for Psychedelic Studies . Denver, CO .
  8. Web site: Better Than Ecstasy: Progress in Developing a Novel Class of Therapeutic with Matthew Baggott, PhD. . YouTube . 6 March 2024 . 20 November 2024.
  9. Johnson CB, Burroughs RL, Baggott MJ, Davidson CJ, Perrine SA, Baker LE . 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 | conference = Society for Neuroscience Conference, Nov. 14, 2022, San Diego, CA | date = 2022 | url = https://www.abstractsonline.com/pp8/#!/10619/presentation/67382 | quote = 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..
  10. Shimshoni JA, Winkler I, Golan E, Nutt D . Neurochemical binding profiles of novel indole and benzofuran MDMA analogues . Naunyn-Schmiedeberg's Archives of Pharmacology . 390 . 1 . 15–24 . January 2017 . 27650729 . 10.1007/s00210-016-1297-4 .
  11. McCann UD, Ricaurte GA . Major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons . Brain Research . 545 . 1–2 . 279–282 . April 1991 . 1860050 . 10.1016/0006-8993(91)91297-E . 2574803 . free .
  12. Miller RT, Lau SS, Monks TJ . 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 . April 1997 . 9128836 . 10.1016/S0014-2999(97)00044-7 .
  13. Conway EL, Louis WJ, Jarrott B . 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 . December 1978 . 729639 . 10.1016/0014-2999(78)90279-0 .
  14. Welter J, Kavanagh P, Meyer MR, Maurer HH . 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 . February 2015 . 25471293 . 10.1007/s00216-014-8360-0 . 20653012 .
  15. Web site: Schedule I . Government Of Canada . 2014-12-12 . 2014-12-13 . https://web.archive.org/web/20131122143804/http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-24.html#h-28 . 2013-11-22 . dead .
  16. Web site: 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" . China Food and Drug Administration . 27 September 2015 . Chinese . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . 1 October 2015 . dead .
  17. Web site: Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie. . Law of February 19, 1973 concerning the sale of medicinal substances and the fight against drug addiction. . French . Journal officiel du Grand-Duché de Luxembourg .
  18. Web site: 'NBOMe' and 'Benzofury' banned . UK Home Office . 2013-06-04 . 10 April 2014.
  19. Web site: The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 . 2014-03-11 . UK Home Office . 2014-03-05 . UK Government.

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