Chemistry:5-MAPB

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5-MAPB, also known as 5-(N-methyl-2-aminopropyl)benzofuran, as well as by nicknames such as "MDMA 2.0" and "Gas Station Molly", is an entactogen of the phenethylamine, amphetamine, and benzofuran families related to MDMA ("Ecstasy").[1][2][3] It is an analogue of MDMA in which one of the oxygen atoms of the benzodioxole ring has been replaced with a carbon atom.[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][2][4][5] 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.[6][1][7][8] It is also an agonist of several serotonin receptors, including the serotonin 5-HT1B, 5-HT2A, 5-HT2B, and 5-HT2C receptors.[6][1][9][10] 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.[11][12] It is said to have been first synthesized in 2009.[2] The drug has been patented by Tactogen for potential use as a medicine to treat psychiatric disorders.[13] It is openly sold as a legal recreational drug in the United States.[2][14] In addition to its use by itself, 5-MAPB is used as a component of the more closely MDMA-mimicking Borax combo.[15][4][16][17]

Use and effects

5-MAPB is an entactogen similarly to MDMA.[1][2] 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.[4][5] However, 5-MAPB is said to be less stimulating than MDMA.[2] In addition, it has been anecdotally claimed to have less of the comedown or hangover of MDMA.[2] 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.[4][5] 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.[15][4][16][17]

Adverse effects

Adverse effects of 5-MAPB are similar to those of MDMA and may include dehydration and hyperthermia, among others.[2] It may also cause serotonergic neurotoxicity like MDMA.[2][18] There have been cases of hospitalization and death in association with 5-MAPB.[19][2][20][21]

Interactions

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.[6][1][7][8] It is also a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[6][1][9] 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.[10]

Monoamine release of 5-MAPB and its enantiomers[13]
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.[13]

5-MAPB has been marketed as a less- or non-neurotoxic alternative to MDMA.[2][18] 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.[2][18]

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.[22][23][24][25] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[26]

Chemistry

Synthesis

The chemical synthesis of 5-MAPB has been described.[10]

Analogues

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

History

5-MAPB was first encountered as a novel designer drug in 2013 and described in the scientific literature in 2014.[11][12] Ezekiel Golan has claimed that he first synthesized 5-MAPB in 2009.[2]

Society and culture

Recreational use

Voyager Labs by Judd Weiss openly sells 5-MAPB as a legal recreational drug in the United States as of the mid-2020s.[2][14][27]

Canada

5-MAPB is not an explicitly listed controlled substance in the Controlled Drugs and Substances Act in Canada.[28] 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.[28]

China

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

Finland

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

Luxembourg

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

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

5-MAPB is not an explicitly controlled substance under the United States Controlled Substances Act.[2] 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.[2][14]

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 "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. 
  2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 2.11 2.12 2.13 2.14 2.15 McConnell, Patrick (4 September 2026). "Is "Gas Station Molly" the Next Big Grey Market Drug?". https://doubleblindmag.com/is-gas-station-molly-the-next-big-grey-market-drug/. 
  3. ↑ "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. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 "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/. Retrieved 27 January 2025. 
  5. ↑ 5.0 5.1 5.2 "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. 
  6. ↑ 6.0 6.1 6.2 6.3 "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. 
  7. ↑ 7.0 7.1 "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. 
  8. ↑ 8.0 8.1 "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. 
  9. ↑ 9.0 9.1 "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. 
  10. ↑ 10.0 10.1 10.2 Matthew Baggott, "Advantageous benzofuran compositions for mental disorders or enhancement", US patent 20230150963, published 2023 May 18, assigned to Tactogen
  11. ↑ 11.0 11.1 "New phenethylamines in Europe". Drug Test Anal 6 (7–8): 808–818. 2014. doi:10.1002/dta.1570. PMID 24574327. 
  12. ↑ 12.0 12.1 "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA". https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013. 
  13. ↑ 13.0 13.1 13.2 Baggott M, "Advantageous benzofuran compositions for mental disorders or enhancement", WO patent 2021/252538, published 16 December 2021
  14. ↑ 14.0 14.1 14.2 Marin, Max (13 April 2026). "Some Philadelphia-area smoke shops sell unregulated psychedelics that often mislead customers". The Philadelphia Inquirer. https://www.inquirer.com/news/a/magic-mushrooms-smoke-shop-drugs-20260412.html. 
  15. ↑ 15.0 15.1 Busby, Mattha (18 August 2025). "Pillheads, Rejoice: There's a New, Improved Ecstasy". VICE. https://www.vice.com/en/article/new-improved-ecstasy-blue-bliss/. 
  16. ↑ 16.0 16.1 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.
  17. ↑ 17.0 17.1 "Borax Combo (Synonyms: Blue Bliss)". National Association of Drug Diversion Investigators (NADDI). 14 December 2022. https://www.naddi.org/glossary/borax-combo/. 
  18. ↑ 18.0 18.1 18.2 "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." 
  19. ↑ "Legislating novel psychoactive substances: lessons from 15 years of UK mortality data (2007-2022)". Front Pharmacol 16. 2025. doi:10.3389/fphar.2025.1708335. PMID 41695988. 
  20. ↑ "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. September 2024. doi:10.1007/s00414-024-03236-w. PMID 38649548. 
  21. ↑ "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. January 2017. doi:10.1016/j.annemergmed.2016.03.042. PMID 27156124. 
  22. ↑ "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. 
  23. ↑ "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. 
  24. ↑ "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. 
  25. ↑ "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. 
  26. ↑ "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. 
  27. ↑ 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.
  28. ↑ 28.0 28.1 "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  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" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  30. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | 1130/2014 | Lainsäädäntö | Finlex". https://finlex.fi/fi/lainsaadanto/2014/1130. 
  31. ↑ "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. 
  32. ↑ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned. 
  33. ↑ 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. 
  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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