Chemistry:5-MAPB

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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]

It has been patented by Tactogen as an entactogen for potential use as a medicine.[2]

Pharmacology

Pharmacodynamics

5-MAPB acts as a serotonin–norepinephrine–dopamine releasing agent with EC50 values for induction of monoamine release of 64 nM for serotonin, 24 nM for norepinephrine, and 41 nM for dopamine using rat brain synaptosomes.[3][4][5][6] It is also a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[3][4][7] In addition, unlike MDMA, it is a potent agonist of the serotonin 5-HT1B receptor.[8]

Monoamine release of 5-MAPB and its enantiomers[2]
Compound SERT NET DAT DAT/SERT ratio
(S)-5-MAPB 67 ND 258 0.26
75% (S)-5-MAPB 80 ND 632 0.13
(RS)-5-MAPB 90 ND 459 0.20
75% (R)-5-MAPB 122 ND 794 0.15
(R)-5-MAPB 184 ND 1951 0.09
Note: This assay used Chinese hamster ovary (CHO) cells expressing human monoamine transporters rather than the more typical rat brain synaptosomes assay.[2]

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.[9][10] 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.[9][10]

5-MAPB has been marketed as a less- or non-neurotoxic alternative to MDMA.[11] 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.[11]

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.[12][13][14][15] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[16]

Society and culture

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.[17]

China

As of October 2015, 5-MAPB is a controlled substance in China.[18]

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".[19]

Luxembourg

As of July 2021, 5-MAPB is not cited in the list of prohibited substances.[20] 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.[21] 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.[22]

See also

References

  1. ↑ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 June 2013. https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds. 
  2. ↑ 2.0 2.1 2.2 Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", WO patent 2021/252538, published 16 December 2021
  3. ↑ 3.0 3.1 "The Toll of Benzofurans in the Context of Drug Abuse". Handbook of Substance Misuse and Addictions. Cham: Springer International Publishing. 2022. p. 1–24. doi:10.1007/978-3-030-67928-6_168-1. ISBN 978-3-030-67928-6. 
  4. ↑ 4.0 4.1 "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". Journal of Psychopharmacology 35 (5): 512–536. May 2021. doi:10.1177/0269881120920420. PMID 32909493. 
  5. ↑ "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. doi:10.1007/s00213-020-05648-z. PMID 32875347. 
  6. ↑ "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. doi:10.1016/j.pnpbp.2016.11.004. PMID 27890676. http://openaccess.sgul.ac.uk/108925/1/Combined_in_vitro_and_in_silico_approaches.pdf. 
  7. ↑ "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues". Naunyn Schmiedebergs Arch Pharmacol 390 (1): 15–24. January 2017. doi:10.1007/s00210-016-1297-4. PMID 27650729. 
  8. ↑ Matthew Baggott, "Advantageous benzofuran compositions for mental disorders or enhancement", US patent 20230150963, published 2023 May 18, assigned to Tactogen
  9. ↑ 9.0 9.1 "Beyond Ecstasy: Progress in Developing and Understanding a Novel Class of Therapeutic Medicine". PS2023 [Psychedelic Science 2023, June 19-23, 2023, Denver, Colorado]. Denver, CO: Multidisciplinary Association for Psychedelic Studies. 23 June 2023. https://2023.psychedelicscience.org/sessions/beyond-ecstasy-progress-in-developing-and-understanding-a-novel-class-of-therapeutic-medicine/. 
  10. ↑ 10.0 10.1 "Better Than Ecstasy: Progress in Developing a Novel Class of Therapeutic with Matthew Baggott, PhD.". 6 March 2024. https://www.youtube.com/watch?v=OnhJvKxwfZI&t=1048. 
  11. ↑ 11.0 11.1 "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. 2022. https://www.abstractsonline.com/pp8/#!/10619/presentation/67382. "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." 
  12. ↑ "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues". Naunyn-Schmiedeberg's Archives of Pharmacology 390 (1): 15–24. January 2017. doi:10.1007/s00210-016-1297-4. PMID 27650729. 
  13. ↑ "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. doi:10.1016/0006-8993(91)91297-E. PMID 1860050. 
  14. ↑ "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. doi:10.1016/S0014-2999(97)00044-7. PMID 9128836. 
  15. ↑ "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. doi:10.1016/0014-2999(78)90279-0. PMID 729639. 
  16. ↑ "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. doi:10.1007/s00216-014-8360-0. PMID 25471293. 
  17. ↑ "Schedule I". Government Of Canada. 2014-12-12. http://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-24.html#h-28. 
  18. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  19. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | 1130/2014 | Lainsäädäntö | Finlex". https://finlex.fi/fi/lainsaadanto/2014/1130. 
  20. ↑ "Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie." (in French). Journal officiel du Grand-Duché de Luxembourg. http://legilux.public.lu/eli/etat/leg/loi/1973/02/19/n1/jo. 
  21. ↑ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned. 
  22. ↑ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. http://www.legislation.gov.uk/ukdsi/2014/9780111110904. 



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