6-MAPB

6-MAPB (1-(benzofuran-6-yl)-N-methylpropan-2-amine) is a psychedelic and entactogenic drug which is structurally related to 6-APB and MDMA.[1][2][3][4] It is not known to have been widely sold as a "designer drug" but has been detected in analytical samples taken from individuals hospitalised after using drug combinations that included other benzofuran derivatives. 6-MAPB was banned in the UK in June 2013, along with 9 other related compounds which were thought to produce similar effects.[5]

6-MAPB
Legal status
Legal status
Identifiers
IUPAC name
  • 1-(Benzofuran-6-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H15NO
Molar mass189.258 g·mol−1
3D model (JSmol)
SMILES
  • CC(NC)CC1=CC(OC=C2)=C2C=C1
InChI
  • InChI=1S/C12H15NO/c1-9(13-2)7-10-3-4-11-5-6-14-12(11)8-10/h3-6,8-9,13H,7H2,1-2H3
  • Key:QLAAURQYEAEHBO-UHFFFAOYSA-N

References
  1. Welter J, Brandt SD, Kavanagh P, Meyer MR, Maurer HH (May 2015). "Metabolic fate, mass spectral fragmentation, detectability, and differentiation in urine of the benzofuran designer drugs 6-APB and 6-MAPB in comparison to their 5-isomers using GC-MS and LC-(HR)-MS(n) techniques". Analytical and Bioanalytical Chemistry. 407 (12): 3457–3470. doi:10.1007/s00216-015-8552-2. PMID 25711990.
  2. Welter-Luedeke J, Maurer HH (February 2016). "New Psychoactive Substances: Chemistry, Pharmacology, Metabolism, and Detectability of Amphetamine Derivatives With Modified Ring Systems". Therapeutic Drug Monitoring. 38 (1): 4–11. doi:10.1097/FTD.0000000000000240. PMID 26327309.
  3. Shimshoni JA, Winkler I, Golan E, Nutt D (January 2017). "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues". Naunyn-Schmiedeberg's Archives of Pharmacology. 390 (1): 15–24. doi:10.1007/s00210-016-1297-4. PMID 27650729.
  4. Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology. 237 (12): 3703–3714. doi:10.1007/s00213-020-05648-z. PMC 7686291. PMID 32875347.
  5. "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-07-10.
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