title: LC-MS/MS quantitative determination of Tetrapterys mucronata alkaloids, a plant occasionally used in ayahuasca preparation.
abstract: BACKGROUND
  Tetrapterys mucronata Cav. (Malpighiaceae) is a plant used in some regions of Brazil in the preparation of ayahuasca.
  
  
  OBJECTIVE
  To determine the content of the main tryptamine alkaloids in the stem bark of T. mucronata Cav. and assess their possible toxic and hallucinogenic properties based on the doses found in a water decoction that mimics the ayahuasca preparation.
  
  
  METHODS
  Four alkaloids previously described for their toxic and hallucinogenic properties were quantitated by multiple reaction monitoring HPLC combined with electrospray ionisation and tandem MS (HPLC-ESI/MS/MS) in the water decoction and ethanolic extracts from the bark of T. mucronata.
  
  
  RESULTS
  Exhaustive extraction of the stem barks with ethanol revealed the following alkaloid levels: bufotenine (1) 3.26 ± 0.31 mg/g, 5-methoxy-N-methyltryptamine (2) 0.88 ± 0.08 mg/g, 5-methoxy-bufotenine (3) 3.07 ± 0.22 mg/g and 2-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (4) 0.14 ± 0.004 mg/g. The water decoction presented slightly lower levels, ranging between 2.32 ± 0.14, 0.50 ± 0.04, 1.53 ± 0.09 and 0.10 ± 0.01 mg/g for (1), (2), (3) and (4) respectively.
  
  
  CONCLUSIONS
  The HPLC-ESI/MS/MS quantitation revealed significant alkaloid levels, in particular for bufotenine and 5-methoxy-bufotenine. As such compounds are known for their toxic and hallucinogenic properties, these results indicate that the consumption of this plant as an ingredient in ayahuasca preparations may present a risk to consumers.
authors.affiliation: Núcleo de Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais (NuBBE), Instituto de Química, Universidade Estadual Paulista (UNESP), Araraquara, São Paulo, Brazil.
authors.forename: M M F
authors.initials: MM
authors.lastname: Queiroz
authors.forename: G
authors.initials: G
authors.lastname: Marti
authors.forename: E F
authors.initials: EF
authors.lastname: Queiroz
authors.forename: L
authors.initials: L
authors.lastname: Marcourt
authors.forename: I
authors.initials: I
authors.lastname: Castro-Gamboa
authors.forename: V S
authors.initials: VS
authors.lastname: Bolzani
authors.forename: J-L
authors.initials: JL
authors.lastname: Wolfender
mesh_terms: D000470:Alkaloids / Q000032:analysis* / Q000737:chemistry; D001938:Brazil; D002027:Bufotenin / Q000031:analogs & derivatives / Q000032:analysis; D002243:Carbolines / Q000032:analysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006213:Hallucinogens / Q000737:chemistry; D029581:Malpighiaceae / Q000737:chemistry*; D024301:Plant Bark / Q000737:chemistry; D012701:Serotonin / Q000031:analogs & derivatives / Q000032:analysis; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: C000607243:2-methyl-6-methoxy-1,2,3,4-tetrahydro-beta-carboline; C000607240:5-methoxy-bufotenine; D000470:Alkaloids; D002243:Carbolines; D006213:Hallucinogens; D002027:Bufotenin; C026864:5-methoxy-alpha-methyltryptamine; D012701:Serotonin
keywords: 5-methoxy-bufotenine; HPLC-ESI/MS/MS quantitation; Malpighiaceae; Tetrapterys mucronata; ayahuasca; bufotenine