title: Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications.
abstract: Preparations of the plant Acorus calamus (calamus or sweet flag) (A. calamus) are available via internet trade and marketed as being hallucinogenic. In 2003-2006, the Swedish Poisons Information Centre received inquiries about 30 clinical cases of intentional intoxication with A. calamus products. The present investigation aimed to identify alpha- and beta-asarone, considered active components of A. calamus, and metabolites thereof in urine samples collected in seven of these cases. To further aid the identification of asarone biotransformation products, a calamus oil preparation was incubated with the fungus Cunninghamella elegans, which is used as a microbial model of mammalian drug metabolism. Using gas chromatography-mass spectrometry (GC-MS) analysis in selected ion monitoring mode, alpha-asarone was detected in five urine samples at concentrations ranging between approximately 11 and 1150 microg/L and beta-asarone in four of those at approximately 22-220 microg/L. A previously identified asarone metabolite, trans-2,4,5-trimethoxycinnamic acid (trans-TMC), was detected in the fungus broth by liquid chromatography-tandem mass spectrometry whereas cis-TMC was tentatively identified in the human urine samples. Using GC-MS, a hydroxylated asarone metabolite was identified both in fungus broth and urine samples. However, this study demonstrated no evidence for the presence of 2,4,5-trimethoxyamphetamine, claimed as a hallucinogenic component of A. calamus. The main clinical symptom reported by the patients was prolonged vomiting that sometimes lasted more than 15 h.
authors.affiliation: Alcohol Laboratory, Department of Clinical Neuroscience, Karolinska Institutet, Stockholm, Sweden.
authors.forename: Kristian
authors.initials: K
authors.lastname: Björnstad
authors.forename: Anders
authors.initials: A
authors.lastname: Helander
authors.forename: Peter
authors.initials: P
authors.lastname: Hultén
authors.forename: Olof
authors.initials: O
authors.lastname: Beck
mesh_terms: D029023:Acorus; D000293:Adolescent; D000328:Adult; D000081248:Allylbenzene Derivatives; D000662:Amphetamines / Q000652:urine; D000840:Anisoles / Q000633:toxicity* / Q000652:urine; D001711:Biotransformation; D002853:Chromatography, Liquid; D002934:Cinnamates / Q000652:urine; D020093:Cunninghamella / Q000378:metabolism; D003640:Dealkylation; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006213:Hallucinogens / Q000633:toxicity* / Q000652:urine; D006801:Humans; D006900:Hydroxylation; D008297:Male; D010938:Plant Oils / Q000378:metabolism / Q000633:toxicity*; D011041:Poisoning / Q000652:urine; D053719:Tandem Mass Spectrometry; D014839:Vomiting / Q000139:chemically induced / Q000652:urine; D055815:Young Adult
chemical_list: D000081248:Allylbenzene Derivatives; D000662:Amphetamines; D000840:Anisoles; D002934:Cinnamates; D006213:Hallucinogens; D010938:Plant Oils; C012195:asarone; C521830:2,4,5-trimethoxyamphetamine