5-MAPB

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5-MAPB
5-MAPB.svg
Systematic (IUPAC) name
1-(Benzofuran-5-yl)-N-methylpropan-2-amine
Clinical data
Legal status
  • AU: Analogue of MDMA
  • CA: Analogue of amphetamine
  • UK: Temporary class drug
  • US: Analogue of MDMA
Routes Oral, Insufflated, Rectal
Identifiers
CAS number 1354631-77-8
ATC code ?
ChemSpider 32078887
Chemical data
Formula C12H15NO 
Mol. 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 and MDMA.[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]

Effects[edit]

Effects of 5-MAPB are generally similar to those of MDMA but with less stimulation, making its effects most closely related to those of MDAI, MMAI, and MBDB. This likely reflects the greater selectivity of 5-MAPB for the serotonin transporter relative to the dopamine or norepinephrine transporter. Users typically report profound empathy and compassion, increased comfort with and acceptance of oneself, lowering of social barriers, and peaceful euphoria.

Legality[edit]

5-MAPB was originally banned in the UK in June 2013 under a Temporary class drug order.[2] 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.[3]

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.[4][5][6] At this time it remains unclear what types of metabolism this molecule experiences in vivo.

See also[edit]

References[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. ^ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. Retrieved 10 April 2014. 
  3. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11. 
  4. ^ McCann UD, Ricaurte GA (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. 
  5. ^ Miller RT, Lau SS, Monks TJ (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. 
  6. ^ Conway EL, Louis WJ, Jarrott B (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.