Case report : A case of β-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract

Giampietro Frison, Donata Favretto, Flavio Zancanaro, Giorgio Fazzin, Santo Davide Ferrara

Forensic Science International, 2008, 179, e37–e43

doi:10.1016/j.forsciint.2008.05.003

 

Abstract

b-Carboline alkaloids harmine, harmaline, and tetrahydroharmine can stimulate the central nervous system by inhibiting the metabolism of amine neurotransmitters, or by direct interaction with specific receptors; they are found in numerous plants, including Peganum harmala, Passiflora incarnata and Banisteriopsis caapi, and in the entheogen preparation Ayahuasca, which is traditionally brewed using B. caapi to enhance the activity of amine hallucinogenic drugs. The ingestion of plant preparations containing b-carboline alkaloids may result in toxic effects, namely visual and auditory hallucinations, locomotor ataxia, nausea, vomiting, confusion and agitation. We report a case of intoxication following intentional ingestion of P. harmala seed infusion; P. harmala seeds were bought over the Internet. The harmala alkaloids were identified by gas chromatography–mass spectrometry in the seed extract and the patient’s urine. This is, to our knowledge, the first case of P. harmala intoxication corroborated by toxicological findings.

Keywords : Peganum harmala; Intoxication; b-Carboline alkaloids; Harmine; Harmaline; Tetrahydroharmine; Peganine

 

1. Introduction

Peganum harmala, also known as Harmal or Syrian rue, is a perennial herbaceous, glabrous plant, that grows in semi-arid conditions, steppe areas and sandy soils, native to eastern Mediterranean region and widely distributed in Central Asia, North Africa and Middle East. It has been used as a traditional
herbal remedy, mainly as an emmenagogue and an abortifacient agent [1–4]; its employ in tribal rites has been reported [5,6]. Turkey P. harmala is called yu¨zerlik or u¨zerli; dried capsules from this plant are hung in homes to protect against ‘‘the evil eye’’. In Iran, dried capsules (known as espænd or esfændda ¯neh) – mixed with other ingredients – are burnt so as to produce a scented smoke that is used as an air as well as mind purifier and mostly as a charm against ‘‘the evil eye’’. This Persian practice seems to date to pre-Islamic times [6]. Due to the psychoactive and hallucinogenic properties of its active components (see below), the use of Harmal in ancient entheogen preparations has been postulated [7,8]. The plant has also been considered as a possible (although doubtful) candidate for the mysterious Soma described in the Rig-Veda or the Haoma of the old Persian Zoroastrian ceremonies [9,10].

The pharmacologically active compounds of P. harmala include a number of b-carboline and quinazoline alkaloids. The possible use of P. harmala in modern phyto-indole entheogen preparations is correlated to its content of b-carbolines: harmine, harmaline and tetrahydroharmine (THH), collectively known as harmala alkaloids. Their chemical structures are shown in Fig. 1. Harmine and harmaline are competitive and reversible inhibitors of monoamine oxidase type-A (MAO-A) enzymes, whereas THH is believed to inhibit serotonin uptake [11,12]. The harmala alkaloids are found mostly in the seeds and the roots, at a concentration of 2–7% by dry weight and are extracted as a tea formulation (infusion). In
recent years, this preparation has become increasingly popular in North America and Europe and is commonly known as ‘‘Ayahuasca analog’’ since it contains the same harmala alkaloids of Ayahuasca [13–15].

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