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5-MAPB

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5-MAPB
Ball-and-stick model of 5-MAPB molecule
Clinical data
Other names5-(N-Methyl-2-aminopropyl)benzofuran
Routes of
administration		Oral, Insufflated, Rectal
Legal status
Legal status
Identifiers
  • 1-(Benzofuran-5-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15NO
Molar mass189.25 g/mol (freebase)
225.7 g/mol (HCl salt) g·mol−1
3D model (JSmol)
  • CC(NC)CC1=CC(C=CO2)=C2C=C1
  • InChI=1S/C12H15NO/c1-9(13-2)7-10-3-4-12-11(8-10)5-6-14-12/h3-6,8-9,13H,7H2,1-2H3
  • Key:ZOVRTIPCNFERHY-UHFFFAOYSA-N

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

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Pharmacodynamics

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5-MAPB acts as a serotonin–norepinephrine–dopamine releasing agent with EC50Tooltip half-maximal effective concentration values for induction of monoamine release of 64 nM for serotonin, 24 nM for norepinephrine, and 41 nM for dopamine using rat brain synaptosomes.[2][3][4][5] It is also a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[2][3][6]

Monoamine release of 5-MAPB and its enantiomers[7]
Compound SERTTooltip Serotonin transporter NETTooltip Norepinephrine transporter DATTooltip Dopamine transporter 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.[7]

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]

5-MAPB has been marketed as a less- or non-neurotoxic alternative to MDMA.[10] 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.[10]

Pharmacokinetics

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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]

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Canada

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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

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As of October 2015 5-MAPB is a controlled substance in China.[17]

Luxembourg

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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

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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]

See also

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References

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  1. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 June 2013. Retrieved 2013-07-10.
  2. ^ a b Roque 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. ISBN 978-3-030-67928-6.
  3. ^ a b Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". Journal of Psychopharmacology. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
  4. ^ Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020). "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. doi:10.1007/s00213-020-05648-z. PMC 7686291. PMID 32875347.
  5. ^ Sahai MA, Davidson C, Khelashvili G, Barrese V, Dutta N, Weinstein H, et al. (April 2017). "Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances - The case of the benzofuran 5-MAPB" (PDF). Progress in Neuro-Psychopharmacology & Biological Psychiatry. 75: 1–9. doi:10.1016/j.pnpbp.2016.11.004. PMID 27890676. S2CID 30943496.
  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. PMID 27650729.
  7. ^ a b WO 2021/252538, Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", published 16 December 2021, assigned to Tactogen Inc. 
  8. ^ a b Baggott M (23 June 2023). 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.
  9. ^ a b "Better Than Ecstasy: Progress in Developing a Novel Class of Therapeutic with Matthew Baggott, PhD". YouTube. 6 March 2024. Retrieved 20 November 2024.
  10. ^ a b Johnson 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.
  11. ^ 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. PMID 27650729.
  12. ^ McCann UD, Ricaurte GA (April 1991). "Major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons". Brain Research. 545 (1–2): 279–282. doi:10.1016/0006-8993(91)91297-E. PMID 1860050. S2CID 2574803.
  13. ^ 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. PMID 9128836.
  14. ^ 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. PMID 729639.
  15. ^ 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. PMID 25471293. S2CID 20653012.
  16. ^ "Schedule I". Government Of Canada. 2014-12-12. Archived from the original on 2013-11-22. Retrieved 2014-12-13.
  17. ^ "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.
  18. ^ "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.]. Journal officiel du Grand-Duché de Luxembourg (in French).
  19. ^ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. Retrieved 10 April 2014.
  20. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
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