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5-MAPB

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5-MAPB
Clinical data
Other names5-(N-Methyl-2-aminopropyl)benzofuran
Routes of
administration		Oral[1]
Drug classEntactogen; Stimulant; Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT1B receptor agonist; Serotonin 5-HT2 receptor agonist
Legal status
Legal status
Pharmacokinetic data
Duration of action5–6 hours[1]
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 of the phenethylamine, amphetamine, and benzofuran families related to MDMA ("Ecstasy").[1][3][4] It is an analogue of MDMA in which one of the oxygen atoms of the benzodioxole ring has been replaced with a methine group.[1] The drug is said to have the closest-known effects to MDMA of any other MDMA analogue, but is said to be less stimulating in comparison and to have less comedown and hangover.[1][3][5][6] In addition, it is more potent than MDMA and has a longer duration.[1]

The drug acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA) similarly to MDMA.[7][1][8][9] It is also an agonist of several serotonin receptors, including the serotonin 5-HT1B, 5-HT2A, 5-HT2B, and 5-HT2C receptors.[7][1][10][11] Some notable analogues of 5-MAPB besides MDMA include other benzofurans like 5-APB, 5-MAPDB, and 6-MAPB.[1]

5-MAPB was first encountered as a novel designer drug in 2013 and was described in the scientific literature in 2014.[12][13] It is said to have been first synthesized in 2009.[3] The drug has been patented by Tactogen for potential use as a medicine to treat psychiatric disorders.[14] It is openly sold as a legal recreational drug in the United States.[3][15] In addition to its use by itself, 5-MAPB is used as a component of the more closely MDMA-mimicking Borax combo.[16][5][17][18]

Use and effects

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5-MAPB is an entactogen similarly to MDMA.[1][3] Its dose is 30 to 70 mg orally and its duration is 5 to 6 hours.[1] The drug has been described by Matthew Baggott as the MDMA analogue with the closest-known effects and so-called "magic" to MDMA itself.[5][6] However, 5-MAPB is said to be less stimulating than MDMA.[3] In addition, it has been anecdotally claimed to have less of the comedown or hangover of MDMA.[3] It appears to be about 2- or 3-fold more potent than MDMA and to have a duration about twice as long.[1] Other analogues of MDMA that similarly lack its full qualities include MBDB, methylone, 6-APDB, 5-APDB, 6-APB, 5-APB, MDAT, and MDAI, among others.[5][6] Whereas certain other analogues like MDA and 6-APB are said to have mild psychedelic effects, 5-MAPB is said to be purely entactogenic.[1] In addition to its use on its own, 5-MAPB, along with the related entactogen MDAI, is employed as a component of the MDMA-mimicking Borax combo, which is said to more closely mimic the effects of MDMA.[16][5][17][18]

Adverse effects

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Adverse effects of 5-MAPB are similar to those of MDMA and may include dehydration and hyperthermia, among others.[3] It may also cause serotonergic neurotoxicity like MDMA.[3][19] There have been cases of hospitalization and death in association with 5-MAPB.[20][3][21][22]

Interactions

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See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

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.[7][1][8][9] It is also a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[7][1][10] In addition, unlike MDMA, it is a relatively potent agonist of the serotonin 5-HT1B receptor, with EC50 values of 161 nM for (S)-5-MAPB and 981 nM for (R)-5-MAPB.[11]

Monoamine release of 5-MAPB and its enantiomers[14]
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.[14]

5-MAPB has been marketed as a less- or non-neurotoxic alternative to MDMA.[3][19] 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.[3][19]

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.[23][24][25][26] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[27]

Chemistry

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Synthesis

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The chemical synthesis of 5-MAPB has been described.[11]

Analogues

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Analogues of 5-MAPB include 5-APB, 5-APDB, 5-MAPDB, 6-APB, 6-MAPB, bk-5-MAPB, 5-MBPB, and others.[1]

History

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5-MAPB was first encountered as a novel designer drug in 2013 and described in the scientific literature in 2014.[12][13] Ezekiel Golan has claimed that he first synthesized 5-MAPB in 2009.[3]

Society and culture

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Recreational use

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Voyager Labs by Judd Weiss openly sells 5-MAPB as a legal recreational drug in the United States as of the mid-2020s.[3][15][28]

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Canada

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5-MAPB is not an explicitly listed controlled substance in the Controlled Drugs and Substances Act in Canada.[2] However, it is an implicitly controlled substance in this country under the act's phenethylamine and amphetamine catch-all clauses, which bans amphetamines as well as phenethylamine benzofurans.[2]

China

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As of October 2015, 5-MAPB is a controlled substance in China.[29]

Finland

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Scheduled in the "government decree on psychoactive substances banned from the consumer market".[30]

Luxembourg

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As of July 2021, 5-MAPB is not cited in the list of prohibited substances.[31] 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.[32] 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.[33]

United States

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5-MAPB is not an explicitly controlled substance under the United States Controlled Substances Act.[3] It is also not named as a controlled substance under California's Uniform Controlled Substances Act.[34] However, 5-MAPB could be considered a controlled substance as an analogue of MDMA under the United States Federal Analogue Act.[3][15]

See also

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References

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  1. ^ a b c d e f g h i j k l m n o p 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.
  2. ^ a b c "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  3. ^ a b c d e f g h i j k l m n o p McConnell P (4 September 2026). "Is "Gas Station Molly" the Next Big Grey Market Drug?". DoubleBlind Mag. Retrieved 13 September 2026.
  4. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 June 2013. Retrieved 2013-07-10.
  5. ^ a b c d e 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. Archived from the original on 14 January 2025. Retrieved 27 January 2025.
  6. ^ a b c "Better Than Ecstasy: Progress in Developing a Novel Class of Therapeutic with Matthew Baggott, PhD". YouTube. 6 March 2024. Retrieved 20 November 2024.
  7. ^ a b c d 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.
  8. ^ a b 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.
  9. ^ a b 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.
  10. ^ a b 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. PMID 27650729.
  11. ^ a b c US 20230150963, Matthew Baggott, "Advantageous benzofuran compositions for mental disorders or enhancement", published 2023 May 18, assigned to Tactogen 
  12. ^ a b King LA (2014). "New phenethylamines in Europe". Drug Test Anal. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
  13. ^ a b "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA". isomerdesign.com.
  14. ^ a b c WO 2021/252538, Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", published 16 December 2021, assigned to Tactogen Inc. 
  15. ^ a b c Marin M (13 April 2026). "Some Philadelphia-area smoke shops sell unregulated psychedelics that often mislead customers". The Philadelphia Inquirer. Retrieved 24 August 2026.
  16. ^ a b Busby M (18 August 2025). "Pillheads, Rejoice: There's a New, Improved Ecstasy". VICE. Retrieved 13 September 2026.
  17. ^ a b Hamilton Morris (28 November 2023). "POD 92: Understanding and Improving MDMA with Dr. Matthew Baggott". The Hamilton Morris Podcast (Podcast). Patreon. Retrieved 30 November 2024.
  18. ^ a b "Borax Combo (Synonyms: Blue Bliss)". naddi.org. National Association of Drug Diversion Investigators (NADDI). 14 December 2022. Retrieved 21 November 2024.
  19. ^ a b c 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.
  20. ^ Rock KL, Treble R, Copeland CS (2025). "Legislating novel psychoactive substances: lessons from 15 years of UK mortality data (2007-2022)". Front Pharmacol. 16 1708335. doi:10.3389/fphar.2025.1708335. PMC 12894293. PMID 41695988.
  21. ^ Epain M, Cartiser N, Bevalot F, Bottinelli C, Chatenay C, Fanton L (September 2024). "Alpha-methyltryptamine and 5-(2-methylaminopropyl)-benzofuran (5-MAPB) fatal co-intoxication: case report and review of literature". Int J Legal Med. 138 (5): 1813–1820. doi:10.1007/s00414-024-03236-w. PMID 38649548.
  22. ^ Hofer KE, Faber K, Müller DM, Hauffe T, Wenger U, Kupferschmidt H, et al. (January 2017). "Acute Toxicity Associated With the Recreational Use of the Novel Psychoactive Benzofuran N-methyl-5-(2 aminopropyl)benzofuran". Ann Emerg Med. 69 (1): 79–82. doi:10.1016/j.annemergmed.2016.03.042. PMID 27156124.
  23. ^ 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. PMID 27650729.
  24. ^ 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.
  25. ^ 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.
  26. ^ 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.
  27. ^ 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.
  28. ^ Morris H (1 April 2026). "POD 142: An interview with 5-MAPB entrepreneur Judd Weiss of Voyager Labs". The Hamilton Morris Podcast (Podcast). Patreon. Retrieved 24 August 2025.
  29. ^ "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.
  30. ^ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | 1130/2014 | Lainsäädäntö | Finlex".
  31. ^ "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).
  32. ^ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. Retrieved 10 April 2014.
  33. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
  34. ^ Cal. Health & Safety Code §§11054–11055 (2025). https://law.justia.com/codes/california/code-hsc/division-10/chapter-2/section-11054/
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