Cited by 30Psychedelics and Drug StudiesSynthesis and bioactivity of alkaloidsForensic Toxicology and Drug Analysis

New insights into the chemical composition of Ayahuasca

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Rodríguez, Luisina, López, Andrés, Moyna, Guillermo, Seoane, Gustavo A., Davyt, Danilo, Vázquez, Álvaro, Hernández, Gonzalo, Carrera, Ignacio·2022·ACS Omega

Abstract

High Resolution Image Download MS PowerPoint Slide Ayahuasca is a psychedelic beverage originally from the Amazon rainforest used in different shamanic settings for medicinal, spiritual, and cultural purposes. It is prepared by boiling in water an admixture of the Amazonian vine Banisteriopsis caapi, which is a source of β-carboline alkaloids, with plants containing N,N -dimethyltryptamine, usually Psychotria viridis . While previous studies have focused on the detection and quantification of the alkaloids present in the drink, less attention has been given to other nonalkaloid components or the composition of the solids suspended in the beverage, which may also affect its psychoactive properties. In this study, we used nuclear magnetic resonance (NMR) and liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) to study the composition of ayahuasca samples, to determine their alkaloid qualitative and quantitative profiles, as well as other major soluble and nonsoluble components. For the first time, fructose was detected as a major component of the samples, while harmine (a β-carboline previously described as an abundant alkaloid in ayahuasca) was found to be present in the solids suspended in the beverage. In addition, N,N -dimethyltryptamine (DMT), harmine, tetrahydroharmine, harmaline, and harmol were identified as the major alkaloids present in extracts of all samples. Finally, a novel, easy, and fast method using quantitative NMR was developed and validated to simultaneously quantify the content of these alkaloids found in each ayahuasca sample.

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Crossref · 10.1021/acsomega.2c00795

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  • Ayahuasca brew batches have varying levels and ratios of alkaloids due to different recipes, cooking methods, and naturally varying alkaloid levels, complicating standardized dosing protocols.

    “Additionally, ayahuasca brew batches have varying levels and ratios of alkaloids due to different recipes including differences in plant combinations and ratios, variations in cooking duration and method, and naturally varying alkaloid levels in the plants used, which complicates the creation of standardized dosing protocols (6, 50).”

    From Potential therapeutic effects of an ayahuasca-inspired N,N-DMT and harmine formulation: a controlled trial in healthy subjects (2024) · cites this paper as [50]

    The Introduction says alkaloid quantities vary with the plant varieties and species used, and Results and Discussion (Quantitative Analysis of Alkaloids; page unavailable) reports differing concentrations and ratios across samples, possibly reflecting different amounts of plants in the preparations. The cited paper does not establish that cooking duration or method causes this variation, or explicitly connect the variation to difficulties creating standardized dosing protocols. (LLM, conf=0.85)

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Research works printed but not linked: 7

  1. Luna L. E. Ayahuasca: A Powerful Epistemological Wildcard in a Complex Fascinating and Dangerous World. Ethnopharmacol. Search Psychoact. Drugs, Synerg. Press 2017, II, 24– 35.
  2. Apud I. Pharmacology of Consciousness or Pharmacology of Spirituality? A Historical Review of Psychedelic Clinical Studies. J. Transpers. Psychol. 2016, 48, 150– 167.
  3. Langdon E. J. Las Clasificaciones Del Yagé Dentro Del Grupo Siona: Etnobotánica, Etnoquímica e Historia. América Indígena 1986, 46, 101– 116.
  4. Scuro J.; Sánchez Petrone V.; Apud I. Las Tradiciones de La Ayahuasca: Su Eco Mediático y Social En El Uruguay. Anu. Antropol. Soc. y Cult. en Uruguay 2013, 11, 55– 69.
  5. Scuro J. Etnografando, Escribiendo e Imaginando: Notas Sobre El Santo Daime En El Uruguay. Anu. Antropol. Soc. y Cult. en Uruguay 2012, 10, 115– 131.
  6. Callaway J. C. Various Alkaloid Profiles in Decoctions of Banisteriopsis Caapi. J. Psychoact. Drugs 2005, 37, 151– 155. 10.1080/02791072.2005.10399796. 16149328 · DOI
  7. Shulgin A. T.; Shulgin A. Tihkal: The Continuation; Transform Press: Berkeley CA, 1997.

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Authors
Rodríguez, L., López, A., Moyna, G., Seoane, G. A., Davyt, D., Vázquez, Á., Hernández, G., & Carrera, I.
Affiliations
  • Universidad de la República de Uruguay (UY)
  • Laboratorio de Resonancia Magnética Nuclear, Departamento de Química Orgánica, Universidad de la República, Avenue General Flores 2124, Montevideo 11800, Uruguay
Corresponding author
  • Vázquez, Álvaro
  • Carrera, Ignacio
Venue
ACS Omega
Published
2022-04-01
Volume
7
Issue
14
Pages
12307-12317
ISSN
2470-1343 (ISSN-L)
OpenAlex
W4224228883
Cited by
30
References
66
Citations by year
2026: 6 · 2025: 5 · 2024: 13 · 2023: 6
FWCI
5.48
Type
journal article
Language
en
Open access
Locations
  • ACS Omega (publishedVersion, cc-by-nc-nd)
  • PubMed Central (publishedVersion, cc-by-nc-nd)
  • PubMed (publishedVersion)
Funders
  • Universidad de la Rep?blica Uruguay
  • Junta Nacional de Drogas - Presidencia de la Rep?blica- Uruguay
Topics
  • Social Sciences › Psychology › Clinical Psychology › Psychedelics and Drug Studies
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Synthesis and bioactivity of alkaloids
  • Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
Keywords
ayahuasca, chemical composition, β-carbolines, harmine, harmaline, harmol, tetrahydroharmine, N,N-dimethyltryptamine, Psychotria viridis, Banisteriopsis caapi, fructose, quantitative NMR, alkaloid quantification

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