5-MAPB

5-MAPB
Ball-and-stick model of 5-MAPB molecule
Systematic (IUPAC) name
1-(Benzofuran-5-yl)-N-methylpropan-2-amine
Clinical data
Routes of
administration		 Oral, Insufflated, Rectal
Legal status
Legal status
Identifiers
CAS Number 1354631-77-8
ChemSpider 32078887
Chemical data
Formula C12H15NO
Molar 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 similar to MDMA on its structure and effects.[1]

Legality

Canada

5-MAPB is not listed itself in the CDSA but since it is structurally related to MDMA it would be considered illegal in Canada.[2]

China

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

UK

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]

Metabolism and toxicity

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]

See also

References

  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; 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.
  7. ↑ 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.
  8. ↑ 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.
  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.
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