Toxicokinetics and Toxicodynamics of Ayahuasca alkaloids N,N-dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: clinical and forensic impact

Brito-da-Costa, Andreia Machado; Dias-da-Silva, Diana; Gomes, Nelson G. M.; Dinis-Oliveira, Ricardo Jorge; Madureira-Carvalho, Áurea

doi:10.3390/ph13110334

Cited by 119Psychedelics and Drug StudiesForensic Toxicology and Drug AnalysisAlkaloids: synthesis and pharmacology

Toxicokinetics and Toxicodynamics of Ayahuasca alkaloids N,N-dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: clinical and forensic impact

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Brito-da-Costa, Andreia Machado, Dias-da-Silva, Diana, Gomes, Nelson G. M., Dinis-Oliveira, Ricardo Jorge, Madureira-Carvalho, Áurea·2020·Pharmaceuticals

DOI 10.3390/ph13110334PMC PMC7690791

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Abstract

Ayahuasca is a hallucinogenic botanical beverage originally used by indigenous Amazonian tribes in religious ceremonies and therapeutic practices. While ethnobotanical surveys still indicate its spiritual and medicinal uses, consumption of ayahuasca has been progressively related with a recreational purpose, particularly in Western societies. The ayahuasca aqueous concoction is typically prepared from the leaves of the N,N-dimethyltryptamine (DMT)-containing Psychotria viridis, and the stem and bark of Banisteriopsis caapi, the plant source of harmala alkaloids. Herein, the toxicokinetics and toxicodynamics of the psychoactive DMT and harmala alkaloids harmine, harmaline and tetrahydroharmine, are comprehensively covered, particularly emphasizing the psychological, physiological, and toxic effects deriving from their concomitant intake. Potential therapeutic utility, particularly in mental and psychiatric disorders, and forensic aspects of DMT and ayahuasca are also reviewed and discussed. Following administration of ayahuasca, DMT is rapidly absorbed and distributed. Harmala alkaloids act as potent inhibitors of monoamine oxidase A (MAO-A), preventing extensive first-pass degradation of DMT into 3-indole-acetic acid (3-IAA), and enabling sufficient amounts of DMT to reach the brain. DMT has affinity for a variety of serotonergic and non-serotonergic receptors, though its psychotropic effects are mainly related with the activation of serotonin receptors type 2A (5-HT2A). Mildly to rarely severe psychedelic adverse effects are reported for ayahuasca or its alkaloids individually, but abuse does not lead to dependence or tolerance. For a long time, the evidence has pointed to potential psychotherapeutic benefits in the treatment of depression, anxiety, and substance abuse disorders; and although misuse of ayahuasca has been diverting attention away from such clinical potential, research onto its therapeutic effects has now strongly resurged.

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Harmine was chosen as MAO-I because it is a major psychoactive molecule of ayahuasca with a favorable side effect profile, lower toxicity compared to harmaline, and is selective and reversible.
“Harmine as a MAO-I was chosen, because it’s a major psychoactive molecule of the ayahuasca brew with a favorable side effect profile, e.g., lower toxicity compared to harmaline, and because it’s selective and reversible (55).”
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 [55]

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Authors: Brito-da-Costa, A. M., Dias-da-Silva, D., Gomes, N. G. M., Dinis-Oliveira, R. J., & Madureira-Carvalho, Á.
Affiliations: Cooperativa de Ensino Superior Politécnico e Universitário (PT)
Department of Sciences, IINFACTS-Institute of Research and Advanced Training in Health Sciences and Technologies, University Institute of Health Sciences (IUCS), CESPU, CRL, 4585-116 Gandra, Portugal
Universidade do Porto (PT)
ORCID: Brito-da-Costa, Andreia Machado
Dias-da-Silva, Diana
Gomes, Nelson G. M.
Dinis-Oliveira, Ricardo Jorge
Madureira-Carvalho, Áurea
Venue: Pharmaceuticals
Publisher: MDPI AG
Published: 2020-10-23
Volume: 13
Issue: 11
Pages: 334
ISSN: 1424-8247 (ISSN-L)
DOI: 10.3390/ph13110334
PMC: PMC7690791
OpenAlex: W3094461574
Cited by: 117
References: 218
Citations by year: 2026: 13 · 2025: 24 · 2024: 25 · 2023: 22 · 2022: 25 · 2021: 7 · 2012: 1
FWCI: 1.06
Type: journal article
Language: en
Open access: gold
doi.org
Licence: cc-by
creativecommons.org/licenses/by/4.0/ (vor)
Locations: Pharmaceuticals (publishedVersion, cc-by)
PubMed Central (publishedVersion, cc-by)
PubMed (publishedVersion)
DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Topics: Social Sciences › Psychology › Clinical Psychology › Psychedelics and Drug Studies
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Alkaloids: synthesis and pharmacology
Keywords: ayahuasca, N,N-dimethyltryptamine, harmine, harmaline, tetrahydroharmine, harmala alkaloids, toxicokinetics, toxicodynamics, monoamine oxidase A inhibition, Psychotria viridis, Banisteriopsis caapi, 5-HT2A receptor, forensic toxicology, psychedelic therapy, depression, anxiety, substance use disorders

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Toxicokinetics and Toxicodynamics of Ayahuasca alkaloids N,N-dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: clinical and forensic impact

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