5-MAPB

From Wikipedia, the free encyclopedia
Jump to: navigation, search
5-MAPB
5-MAPB.svg
Systematic (IUPAC) name
1-(Benzofuran-5-yl)-N-methylpropan-2-amine
Clinical data
Legal status Analogue of MDMA (AU) Analogue of amphetamine (CA) Temporary class drug (UK) Analogue of MDMA (US)
Routes Oral, Insufflated, Rectal
Identifiers
CAS number 1354631-77-8
ATC code ?
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]

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 striking similarity with 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.[4][5][6] If the two carbons between the oxygen and benzyl ring were cleaved from this structure, the resulting molecule would be pholedrine and the metabolic path would produce 4-Hydroxyamphetamine (alpha-methyltyramine) and then through beta-oxidation para-hydroxynorephedrine. At this time it is 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.