5-MAPB

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5-MAPB
5-MAPB.svg
Ball-and-stick model of 5-MAPB molecule
Clinical data
Routes of
administration
Oral, Insufflated, Rectal
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C12H15NO
Molar mass 189.25 g/mol (freebase)
225.7 g/mol (HCl salt)
3D model (JSmol)

5-MAPB (1-(benzofuran-5-yl)-N-methylpropan-2-amine) is an entactogenic designer drug similar to MDMA on its structure and effects.[1]

Legal Status[edit]

Canada[edit]

5-MAPB is not listed itself in the CDSA but since it is structurally related to MDMA it may be considered illegal in Canada, although this has not been tested in court.[2]

China[edit]

As of October 2015 5-MAPB is a controlled substance in China.[3]

United Kingdom[edit]

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

Pharmacokinetics[edit]

Metabolism and toxicity[edit]

Little formal knowledge exists on 5-MAPB. It does not share the neurotoxicity of MDA caused by the alpha-methyldopamine metabolite.[6][7][8] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[9]

Pharmacodynamics[edit]

5-MAPB binds to the dopamine transporter in rat brain cells with a lower potency than cocaine. In silico data suggests that the primary action on dopamine is through reversal of the transporter to release dopamine. This is consistent with the effects and it is likely that it exerts a similar action on serotonin and norepinephrine transporters.[10]

References[edit]

  1. ^ "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. ^ "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. Retrieved 1 October 2015. 
  4. ^ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. Retrieved 10 April 2014. 
  5. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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): 1371–88. doi:10.1007/s00216-014-8360-0. PMID 25471293. 
  10. ^ Sahai, Michelle A; Davidson, Colin; Khelashvili, George (2016). "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 and Biological Psychiatry. 75: 1–9. doi:10.1016/j.pnpbp.2016.11.004.