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Ball-and-stick model of 5-MAPB molecule
Systematic (IUPAC) name
Clinical data
Legal status
  • AU: Analogue of MDMA
  • CA: Analogue of amphetamine
  • UK: Temporary class drug
  • US: Analogue of MDMA
Routes of
Oral, Insufflated, Rectal
CAS Registry Number 1354631-77-8
ChemSpider 32078887
Chemical data
Formula C12H15NO
Molecular mass 189.25 g/mol (freebase)
225.7 g/mol (HCl salt)

5-MAPB (1-(benzofuran-5-yl)-N-methylpropan-2-amine) is an entactogenic designer drug which is structurally related to 5-APB, MDMA and methamphetamine.[1] It has similar effects to these drugs in humans and has been used as a recreational drug.[1] 5-MAPB was temporarily banned in the UK in June 2013 after being detected being used as a street drug and sold online, along with 9 other related compounds.[1]


5-MAPB is not itself listed in the CDSA but since it is an amphetamine and analog thereof it would be considered illegal in Canada.[2]

5-MAPB was originally banned in the UK in June 2013 under a Temporary class drug order.[3] 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.[4]

Metabolism and toxicity[edit]

Little formal knowledge exists on 5-MAPB. User reports suggest effects similar to MDMA, 5-MAPB shares structural relation to MDMA, however it is unlikely to produce the metabolite speculated by some to be the major factor in the neurotoxicity of MDMA; 2,5-bis-(glutathion-S-yl)-alpha-methyldopamine or the major psychedelic metabolite MDA.[5][6][7] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[8]

See also[edit]


  1. ^ a b c "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-07-10. 
  2. ^ "'Schedule I'". Government Of Canada. 2014-12-12. 
  3. ^ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. Retrieved 10 April 2014. 
  4. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11. 
  5. ^ McCann UD, Ricaurte GA; Ricaurte (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. 
  6. ^ Miller RT, Lau SS, Monks TJ; Lau; Monks (1997). "2,5-Bis-(glutathion-S-yl)-alpha-methyldopamine, a putative metabolite of (+/-)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations". Eur J Pharmacol. 323 (2–3): 173–80. doi:10.1016/S0014-2999(97)00044-7. PMID 9128836. 
  7. ^ Conway EL, Louis WJ, Jarrott B; Louis; Jarrott (1978). "Acute and chronic administration of alpha-methyldopa: regional levels of endogenous and alpha-methylated catecholamines in rat brain". Eur J Pharmacol. 52 (3–4): 271–80. doi:10.1016/0014-2999(78)90279-0. PMID 729639. 
  8. ^ Welter, Jessica; Kavanagh, Pierce; Meyer, Markus R.; Maurer, Hans H. (2014). "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)-MSn techniques". Analytical and Bioanalytical Chemistry 407 (5): 1371. doi:10.1007/s00216-014-8360-0. PMID 25471293.