Cited by 362Synthesis and bioactivity of alkaloidsAlkaloids: synthesis and pharmacologyForensic Toxicology and Drug Analysis

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β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)

Herraiz, T., González, D., Ancín-Azpilicueta, C., Arán, V.J., Guillén, H.·2010·Food and Chemical Toxicology

DOI 10.1016/j.fct.2009.12.019

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Abstract

Peganum harmala L. is a multipurpose medicinal plant increasingly used for psychoactive recreational purposes (Ayahuasca analog). Harmaline, harmine, harmalol, harmol and tetrahydroharmine were identified and quantified as the main beta-carboline alkaloids in P. harmala extracts. Seeds and roots contained the highest levels of alkaloids with low levels in stems and leaves, and absence in flowers. Harmine and harmaline accumulated in dry seeds at 4.3% and 5.6% (w/w), respectively, harmalol at 0.6%, and tetrahydroharmine at 0.1% (w/w). Roots contained harmine and harmol with 2.0% and 1.4% (w/w), respectively. Seed extracts were potent reversible and competitive inhibitors of human monoamine oxidase (MAO-A) with an IC(50) of 27 microg/l whereas root extracts strongly inhibited MAO-A with an IC(50) of 159 microg/l. In contrast, they were poor inhibitors of MAO-B. Inhibition of MAO-A by seed extracts was quantitatively attributed to harmaline and harmine whereas inhibition by root extracts came from harmine with no additional interferences. Stems and leaves extracts were poor inhibitors of MAO. The potent inhibition of MAO-A by seed and root extracts of P. harmala containing beta-carbolines should contribute to the psychopharmacological and toxicological effects of this plant and could be the basis for its purported antidepressant actions.

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Herraiz, T., Sánchez-Arroyo, A., Rivas, B. D. L., Landete, J. M., & Múñoz, R. (2026) · Scientific Reports · doi:10.1038/s41598-026-35162-9 · Cited by 3
The Level of Reactive Carbonyl Derivatives of Proteins, Malondialdehyde, and Catalase Activity in the Brain of Rats after Therapy Following Chronic Unpredictable Moderate Stress
Yepifantseva, Y. V., Абдрахманова, М. Г., Pozdnyakova, Y. V., Semenikhina, P. S., Беляев, Р. А., Stupina, T. A., Beisembayeva, M., & Adekenov, S. M. (2020) · Open Access Macedonian Journal of Medical Sciences · doi:10.3889/oamjms.2020.5396 · Cited by 4
“Beta-carboline alkaloids exhibit a wide range of psychopharmacological effects, binding to benzodiazepine, imidazoline, serotonin, and opiate receptors, as well as inhibiting MAO [11].”
Background
Profiling the volatile compounds of Peganum harmala L. Based on multiple sample preparation coupled with gas chromatography-mass spectrometry analysis and explored its antidepressants-like activity
Zhu, Y., Cheng, F., Lu, X., Ma, X., Reyanggu, A., Bakri, M., & Maiwulanjiang, M. (2024) · Journal of Chromatography B · doi:10.1016/j.jchromb.2024.124232 · Cited by 4
Dissecting the role of SMN multimerization in its dissociation from the Cajal body using harmine as a tool compound
Ohazama, S., Fujimoto, A., Konda, D., Yokoyama, R., Nakagawa, S., & Maita, H. (2024) · Journal of Cell Science · doi:10.1242/jcs.261834 · Cited by 4
Influence of some plant extracts and commercial insecticides on the eggs ofTrialeurodes vaporariorumWestwood (Homoptera: Aleyrodidae)
Dehghani, M., & Ahmadi, K. (2013) · Archives of Phytopathology and Plant Protection · doi:10.1080/03235408.2012.760261 · Cited by 4
“According to the recent studies, Peganum harmala L., a member of the Zygophyllaceae family, known for the exceptional wealth including harmane, harmine, harmaline, harmalol, tetrahydroharmine and peganine (Pulpati et al. 2008; Herraiz et al. 2010).”
BackgroundResult
Polycoccum Hawksworthianum (Polycoccaceae, Trypetheliales), A New Lichenicolous Fungus on Lepra and Varicellaria from India
Joshi, Y. C. (2020) · Acta Botanica Hungarica · doi:10.1556/034.62.2020.3-4.2 · Cited by 4
In vitro anti-parasitic activity and mechanism of β-carboline derivatives isolated from the extracellular product of Salinivibrio proteolyticus strain YCSC6
Du, G., Sun, C., Liu, Y., Dong, Q., Gao, P. H., Li, D., & Qu, L. (2020) · Aquaculture · doi:10.1016/j.aquaculture.2020.736337 · Cited by 4
Peganum harmala: Phytochemistry, Traditional Uses, and Biological Activities
Mamadalieva, N. Z., Ashour, M. L., & Mamedov, N. (2022) · Springer eBooks · doi:10.1007/978-3-030-73943-0_40 · Cited by 4
Ameliorative effects of Pergamum harmala seed extract on obese diabetic rats
Magdy, N., Salama, M., Alsaedy, Y., & El‐Sayed, G. (2020) · Mansoura Veterinary Medical Journal · doi:10.21608/mvmj.2020.21.319 · Cited by 4
“Harmala belongs to zygophylaceae family which has a wide range of medicinal properties due to presence of betacarboline alkaloids as harmine, harmaline, harmalol and harmol [8].”
BackgroundInfluential
Basolateral amygdala cannabinoid CB1 receptors mediate the antinociceptive activity of harmaline in adolescent male mice
Alijanpour, S., Ghasemzadeh, Z., Ebrahimi-Ghiri, M., & Zarrindast, M. (2022) · Physiology & Behavior · doi:10.1016/j.physbeh.2022.113886 · Cited by 5
Analgesic and Antidepressant Activity of 8-Substituted Harmine Derivatives
Сейдахметова, Р. Б., Аманжан, А., Shults, E. E., Goldaeva, K. V., Adekenov, S. M., & Berillo, D. A. (2022) · Chemistry of Heterocyclic Compounds · doi:10.1007/s10593-022-03092-9 · Cited by 4
Potent inhibition of human organic cation transporter 2 (hOCT2) by β-carboline alkaloids
Wagner, D. J., Duan, H., Chapron, A., Lee, R. W., & Wang, J. (2016) · Xenobiotica · doi:10.1080/00498254.2016.1271160 · Cited by 4
“They can be found in well-cooked meats and fish, coffee, chocolate, alcoholic beverages, tobacco smoke, as well as in herbal products used in traditional medicine or for recreational purpose (Herraiz et al., 2010; Herraiz, 2000a,b, 2004; Nussberger et al., 1987; Totsuka et al., 1999).”
Influential
The effect of harmaline on seizures induced by amygdala kindling in rats
Alenajaf, A., Mohebbi, E., Moghimi, A., Fereidoni, M., & Mohammad‐Zadeh, M. (2019) · Neurological Research · doi:10.1080/01616412.2019.1580460 · Cited by 4
“Moreover, the proconvulsant effect of harmaline can be due to the inhibition of MAO-A and MAO-B [30] activity and the consequent increase in dopaminergic transmission [31], and in serotonin level [32] in nerve synapses.”
Background
[Psychoactive plant species--actual list of plants prohibited in Poland].
Simonienko, K., Waszkiewicz, N., & Szulc, A. (2013) · PubMed · Cited by 4
Effect of Alkaloids Belong to β-Carbolines Family in Peganum Harmala on Cancer Cells
Roostaee, Z. (2017) · Sarem Journal of Reproductive Medicine · doi:10.29252/sjrm.2.2.73 · Cited by 4
Six-membered N-heterocyclic alkaloids as ChE inhibitors in alzheimer’s disease treatment
Yadav, P., Dabas, A., & Singh, R. (2025) · Metabolic Brain Disease · doi:10.1007/s11011-025-01740-5 · Cited by 3
“The seeds of P. harmala contain 4.3% harmine, whereas roots contain 2% of this alkaloid (Herraiz et al. 2010).”
Influential
Safety and Efficacy of Monoamine Oxidase Inhibitors in Patients Who Use Psychoactive Substances: Potential Drug Interactions and Substance Use Disorder Treatment Data
Rached, G., Campana, A. M., Fiani, D., Nguyen, C. Y., den Eynde, V. V., Gillman, P. K., & Barnett, B. S. (2026) · CNS Drugs · doi:10.1007/s40263-025-01256-7 · Cited by 3
Identification, Occurrence, and Mechanism of Formation of 1-Acetyl-β-carbolines Derived from l -Tryptophan and Methylglyoxal
Herraiz, T., Salgado, A., & Peña, A. (2025) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.4c09130 · Cited by 3
Chemoselective aminomethylation of harmol
Bondarenko, S. P., Іщенко, В. М., & Frasinyuk, M. S. (2018) · Chemistry of Heterocyclic Compounds · doi:10.1007/s10593-018-2392-x · Cited by 3
Pharmacology and Structure-Activity Relationship of Natural Products With Psychoactive Effects From Salvia divinorum, Mitragyna speciosa, and Ayahuasca
Phipps, S. M., & Grundmann, O. (2017) · Studies in natural products chemistry · doi:10.1016/b978-0-444-63930-1.00001-6 · Cited by 3
LC‐HRMS for the Identification of β‐Carboline and Canthinone Alkaloids Isolated from Natural Sources
Amaral, A. C. F., Ramos, A. D. S., Ferreira, J. L. P., dos Santos, A. R., da Cruz, J. D., de Luna, A. V., Nery, V. V. C., Lima, I. C., Chaves, M. H. D. C., & Silva, J. R. D. A. (2017) · InTech eBooks · doi:10.5772/68075 · Cited by 3
Ayahuasca, Harmala Alkaloids, and Dimethyltryptamines
Barceloux, D. G. (2012) · doi:10.1002/9781118105955.ch53 · Cited by 3
Heterocyclic aromatic amines (HAAs) target mitochondrial physiologyPreprint
Sammi, S. R., Syeda, T., Foguth, R. M., & Cannon, J. R. (2022) · bioRxiv (Cold Spring Harbor Laboratory) · doi:10.1101/2022.03.17.484822 · Cited by 3
Enhancing mindfulness and compassion through an ayahuasca-inspired formulation containing N,N-DMT and harmine: A randomized controlled trial in healthy subjects
Aicher, H., Wicki, I. A., Meling, D., Mueller, M. J., Dornbierer, D., & Scheidegger, M. (2025) · Journal of Psychopharmacology · doi:10.1177/02698811251344689 · Cited by 2
“This finding could be explained via the nonspecific serotonergic stimulation effects that are described for the MAO-A inhibitor harmine (Herraiz et al., 2010).”
Comprehensive review of β-carbolines from microbes and their biosynthesis
Twumasi, M. A., Kusche, M. P., Baig, A. F., Nybo, S. E., & Kharel, M. K. (2026) · European Journal of Medicinal Chemistry Reports · doi:10.1016/j.ejmcr.2026.100330 · Cited by 2
Phytochemical Characterization and Antioxidant Potential of Peganum harmala L. Seeds: A Natural Source of Bioactive Compounds.
Tepe, M. (2026) · Türk doğa ve fen dergisi :/Türk doğa ve fen dergisi · doi:10.46810/tdfd.1761584 · Cited by 2
Simple naturally occurring β-carboline alkaloids – role in sustainable theranostics
Bhattacharya, P., & De, S. (2022) · Physical Sciences Reviews · doi:10.1515/psr-2022-0132 · Cited by 2
Rumors of Psychedelics, Psychotropics and Related Derivatives in Vachellia and Senegalia in Contrast with Verified Records in Australian Acacia
Sadgrove, N. J. (2022) · Plants · doi:10.3390/plants11233356 · Cited by 2
“Because harmala alkaloids are poor inhibit s of MAO-B [40], phenethylami s are ge erally not capable f being substituted for tryp amines in ayahuasca preparations.”
BackgroundInfluential
Comparison of five DNA extraction methods in three medicinal plants: Peganum harmala L., Tamarix ramosissima Ledeb., and Potentilla reptans L.
Salehi, Z., Amirahmadi, A., Rezaei, A., Farrokh, P., & Ghasemian, J. (2023) · PubMed Central · doi:10.22099/mbrc.2023.45131.1798 · Cited by 2
“P. harmala, known as espand in Persian, is a perennial herbaceous plant native to the arid regions of North Africa, the Mediterranean, the Middle East, Pakistan, and India [11].”
BackgroundInfluential
Impact of Peganum harmala/Zinc Oxide Nanoparticles on Thyroid and Pancreatic Function in Obese Rats: A Biochemical and Physiological Analysis
Abdelsatta, M., Elseady, Y., Hendawy, A., Diab, A. E.-A. A., Awadin, W. F., & Eldesoqui, M. B. (2024) · International Journal of Pharmacology · doi:10.3923/ijp.2024.981.990 · Cited by 3
Total Synthesis of 6‑Hydroxymetatacarboline‑ d Discovered from Mycena metata via the Pictet–Spengler Reaction Followed by the Horner–Wadsworth–Emmons Reaction
Kumar, D., Vaya, D., & Chundawat, T. S. (2021) · ACS Omega · doi:10.1021/acsomega.0c06202 · Cited by 2
MODULATORY EFFECT OF HARMINE ON SPATIAL MEMORY, FERTILITY VIA MAO INHIBITION, PREVENTING ANEMIA AND ANTI-NOCICEPTION UPON FOOTSHOCK STRESS AT THREE STAGES OF PREGNANT RATS
Benatoui, R., Bairi, A., & Tahraoui, A. (2021) · Universal Journal of Pharmaceutical Research · doi:10.22270/ujpr.v6i5.671 · Cited by 3
Assay of MAO Inhibition by Chromatographic Techniques (HPLC/HPLC-MS)
Herraiz, T. (2022) · Methods in molecular biology · doi:10.1007/978-1-0716-2643-6_8 · Cited by 2
Innovative spectrofluorometric method for determination of harmaline and harmine in different matrices
Abdelazim, A. H., Algarni, M. A., & Almalki, A. H. (2023) · Scientific Reports · doi:10.1038/s41598-023-46041-y · Cited by 2
Neuropharmacological evaluation of selected Jordanian traditional herbal medicines
Abuhamdah, S. M. A., Abuhamdah, R. M. A., Shakya, A. K., Al-Olimat, S., & Chazot, P. L. (2014) · African Journal of Pharmacy and Pharmacology · doi:10.5897/ajpp2014.4097 · Cited by 2
“This result indicates that AChE is inhibited reversibly by A. citrodora and irreversibly by P. harmala (Cao et al., 2007; Herraiz et al., 2010; Sobhani et al., 2002).”
Result
Chemical Analysis of Population Variability in Peganum Harmala (var. Harmala)
Gholami, T., Peyvandi, M., Abbaspour, H., Noormohammadi, Z., & Sharifnia, F. (2020) · Acta Botanica Hungarica · doi:10.1556/034.62.2020.3-4.1 · Cited by 1
The Antinociceptive Effects of Central and Peripheral Administration of Peganum harmala L. Extracts in Animal Models
Aboufatima, R., Farouk, L., Laaradia, M. A., Oufquir, S., Laadraoui, J., Alami, A. E., Gabbas, Z. E., Bezza, K., Marhoume, F., Sokar, Z., et al. (2021) · OnLine Journal of Biological Sciences · doi:10.3844/ojbsci.2021.267.279 · Cited by 1
“Harmine, Harmala, Harmaline, Harmalol and Harman alkaloids are the psychological active ingredients of P. harmala seeds, which are also found widely in a variety of herbal medicines (Cao et al., 2007; Herraiz et al., 2010).”
Background
EXPLORATION OF HALLUCINOGENIC COMPOUNDS IN PEGANUM HARMALA, A POPULAR INCENSE IN FOLK CULTURE, COUPLED WITH ANATOMICAL ANALYSIS
Akdoğan, M., Tekman, E., Yuca, H., Karakaya, S., Bona, G. E., & Kazaz, C. (2025) · Ankara Universitesi Eczacilik Fakultesi Dergisi · doi:10.33483/jfpau.1532753 · Cited by 1
EVALUATION OF CHEMICAL COMPONENTS, ANTI-OXIDANT PROPERTIES, AND LETHAL TOXICITY OF ALKALOIDS EXTRACTED FROM ESPAND (Peganum harmala)
Saeedeh, F., Oryan, S., Ahmadi, R., & Eidi, A. (2022) · Journal of Applied Biological Sciences · doi:10.71336/jabs.971 · Cited by 1
“Harmaline is found in seeds, but Harmol is found in roots and stems [8].”
An Update to Alkaloids Derived from Tryptophan: Harmine and Relative Alkaloids
Nikam, T. D., Nitnaware, K. M., Mali, A. A., & Ahire, M. L. (2025) · Springer eBooks · doi:10.1007/978-3-642-36202-6_20-1 · Cited by 1
Herbs Acting in the CNS
León, F., Zakid, A. A., Gupta, S., Mukhopadhyay, S., Tarawneh, A. H., Obeng, S., Cutler, S. J., & McCurdy, C. R. (2025) · Elsevier eBooks · doi:10.1016/b978-0-323-95702-1.00490-5 · Cited by 1
Chemical fingerprinting of Peganum harmala seeds via UV–Vis, XRD, TGA, FTIR, and GC-MS techniques; In vitro assessment of cytotoxic properties
Sunil, S., & Amruth, P. (2025) · Toxicon · doi:10.1016/j.toxicon.2025.108606 · Cited by 1
Ultrasensitive spectrofluorimetric analysis of harmalacidine HCl: A potent underexplored MAO-A inhibitor from Peganum harmala L
Alossaimi, M. A., ElNaggar, M. H., Magdy, G., Mourenza, Á., Mateos, L. M., Letek, M., & Bar, F. M. A. (2025) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2025.127056 · Cited by 1

Authors: Herraiz, T., González, D., Ancín-Azpilicueta, C., Arán, V. J., & Guillén, H.
Affiliations: Consejo Superior de Investigaciones Científicas (ES)
Instituto de Química Médica (ES)
Corresponding author: Herraiz, T.
ORCID: Herraiz, T.
Arán, V.J.
Guillén, H.
Venue: Food and Chemical Toxicology
Publisher: Elsevier BV
Published: 2010-03
Volume: 48
Issue: 3
Pages: 839-845
ISSN: 0278-6915 (ISSN-L)
DOI: 10.1016/j.fct.2009.12.019
OpenAlex: W2169624105
Cited by: 357
References: 59
Citations by year: 2026: 31 · 2025: 24 · 2024: 16 · 2023: 25 · 2022: 27 · 2021: 25 · 2020: 26 · 2019: 26 · 2018: 18 · 2017: 19 · 2016: 21 · 2015: 18 · 2014: 23 · 2013: 23 · 2012: 12
FWCI: 4.69
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Food and Chemical Toxicology (publishedVersion)
PubMed (publishedVersion)
DIGITAL.CSIC (Spanish National Research Council (CSIC)) (submittedVersion)
Funders: Spanish government (AGL2006-02414)
CSIC (200470E658)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Synthesis and bioactivity of alkaloids
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Alkaloids: synthesis and pharmacology
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
Keywords: Peganum harmala, β-carbolines, harmine, harmaline, harmol, tetrahydroharmine, harmalol, monoamine oxidase A inhibition, monoamine oxidase B inhibition, seeds, roots, antidepressant effects, psychopharmacology, toxicology
MeSH terms: Carbolines, Chromatography, High Pressure Liquid, Harmaline, Harmine, Humans, Kinetics, Monoamine Oxidase, Monoamine Oxidase Inhibitors, Plant Extracts, Seeds, Spectrophotometry, Ultraviolet, Plant Roots, Spectrometry, Mass, Electrospray Ionization, Peganum

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β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)

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