cycasin
 
Notes:
Alkaloid from seeds of the false sago Cycas circinalis and sago cycas Cycas revoluta (Cycadaceae). Carcinogen of significance in human nutrition; but in practice the toxin is present in the seeds of the plant and the pith is used as a food source
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CAS Number: 14901-08-7Picture of molecule3D/inchi
FDA UNII: 9H51HL0E1D
Beilstein Number: 0025396
XlogP3: -2.60 (est)
Molecular Weight: 252.22392000
Formula: C8 H16 N2 O7
NMR Predictor: Predict (works with chrome or firefox)
Category: toxic natural substances
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-guinea pig LD50  20 mg/kg
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 31, Pg. 1493, 1972.

oral-hamster LD50  250 mg/kg
BEHAVIORAL: ATAXIA
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 31, Pg. 1493, 1972.

oral-mouse LD50  500 mg/kg
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 31, Pg. 1493, 1972.

oral-rabbit LD50  30 mg/kg
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 31, Pg. 1493, 1972.

oral-rat LD50  270 mg/kg
Gann. Japanese Journal of Cancer Research. Vol. 62, Pg. 353, 1971.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: toxic natural substances
Recommendation for cycasin usage levels up to:
 not for fragrance use.
 
Recommendation for cycasin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA GENetic TOXicology: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5459896
National Institute of Allergy and Infectious Diseases: Data
 (Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium
Chemidplus: 0014901087
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References:
 (Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5459896
Pubchem (cas): 14901-08-7
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C01418
HMDB (The Human Metabolome Database): HMDB38850
FooDB: FDB018287
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cycas circinalis seed
Search Trop  Picture
 cycas revoluta seed
Search Trop  Picture
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Synonyms:
beta-D-glucopyranoside, (methyl-ONN-azoxy)methyl-
beta-D-glucosyloxyazoxymethane
(methyl-ONN-azoxy)-methyl-beta-D-glucopyranoside
(Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium
 methylazoxymethanolbeta-D-glucoside
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Articles:
PubMed: Toxic phytochemicals and their potential risks for human cancer.
PubMed: Relative seed and fruit toxicity of the Australian cycads Macrozamia miquelii and Cycas ophiolitica: further evidence for a megafaunal seed dispersal syndrome in cycads, and its possible antiquity.
PubMed: Effect of methanolic extract of Vernonia amygdalina (common bitter leaf) on lipid peroxidation and antioxidant enzymes in rats exposed to cycasin.
PubMed: Animal models of brain maldevelopment induced by cycad plant genotoxins.
PubMed: Cycads and their association with certain neurodegenerative diseases.
PubMed: Unraveling 50-Year-Old Clues Linking Neurodegeneration and Cancer to Cycad Toxins: Are microRNAs Common Mediators?
PubMed: Does the cycad genotoxin MAM implicated in Guam ALS-PDC induce disease-relevant changes in mouse brain that includes olfaction?
PubMed: Is neurodegenerative disease a long-latency response to early-life genotoxin exposure?
PubMed: Antileishmanial, antitrypanosomal, and cytotoxic screening of ethnopharmacologically selected Peruvian plants.
PubMed: The cycad genotoxin MAM modulates brain cellular pathways involved in neurodegenerative disease and cancer in a DNA damage-linked manner.
PubMed: Two genera of Aulacoscelinae beetles reflexively bleed azoxyglycosides found in their host cycads.
PubMed: A survey of phytotoxic microbial and plant metabolites as potential natural products for pest management.
PubMed: [Studies on the chemical constituents of the roots of Anemone altaica].
PubMed: Return of the cycad hypothesis - does the amyotrophic lateral sclerosis/parkinsonism dementia complex (ALS/PDC) of Guam have new implications for global health?
PubMed: Molecular networks perturbed in a developmental animal model of brain injury.
PubMed: Azoxyglycoside content and beta-glycosidase activities in leaves of various cycads.
PubMed: Acute Cycas seed poisoning in Taiwan.
PubMed: Western Pacific ALS/PDC and flying foxes: What's next?
PubMed: Cycads: their evolution, toxins, herbivores and insect pollinators.
PubMed: Behavioral and neurological correlates of ALS-parkinsonism dementia complex in adult mice fed washed cycad flour.
PubMed: Toxicology. Fruit bats linked to mystery disease.
PubMed: Cycad neurotoxins, consumption of flying foxes, and ALS-PDC disease in Guam.
PubMed: Effects of single injection of methylazoxymethanol at postnatal day one on cell proliferation in different brain regions of male rats.
PubMed: SOS induction of selected naturally occurring substances in Escherichia coli (SOS chromotest).
PubMed: Damage and repair of nerve cell DNA in toxic stress.
PubMed: The Guam cycad toxin methylazoxymethanol damages neuronal DNA and modulates tau mRNA expression and excitotoxicity.
PubMed: Cycad poisoning in cattle in Japan--studies on spontaneous and experimental cases.
PubMed: Are age-related neurodegenerative diseases linked with various types of magnesium depletion?
PubMed: Na+-dependent and phlorizin-inhibitable transport of glucose and cycasin in brain endothelial cells.
PubMed: ApoE and CYP2D6 polymorphism with and without parkinsonism-dementia complex in the people of Chamorro, guam.
PubMed: Neuroepidemiology of amyotrophic lateral sclerosis: clues to aetiology and pathogenesis.
PubMed: Motor neuron disease on Guam: geographic and familial occurrence, 1956-85.
PubMed: Potential role of environmental genotoxic agents in diabetes mellitus and neurodegenerative diseases.
PubMed: Substrate specificity and transglucosylation catalyzed by cycad beta-glucosidase.
PubMed: A partially purified beta-glucosidase from Bifidobacterium adolescentis converts cycasin to a mutagenic compound.
PubMed: Cycad toxin-induced damage of rodent and human pancreatic beta-cells.
PubMed: Genotoxic activity in vivo of the naturally occurring glucoside, cycasin, in the Drosophila wing spot test.
PubMed: Early biochemical events in mice exposed to cycas and fed a Nigerian-like diet.
PubMed: Transport of cycasin by the intestinal Na+/glucose cotransporter.
PubMed: The magical and medicinal usage of Stangeria eriopus in South Africa.
PubMed: Tumor incidence in a chemical carcinogenesis study of nonhuman primates.
PubMed: Seeds of discovery: a new look at one environmental factor in Alzheimer's disease.
PubMed: Guam ALS-PDC: possible causes.
PubMed: Content of the neurotoxins cycasin (methylazoxymethanol beta-D-glucoside) and BMAA (beta-N-methylamino-L-alanine) in cycad flour prepared by Guam Chamorros.
PubMed: Long-latency neurodegenerative disease in the western Pacific.
PubMed: Slow toxins, biologic markers, and long-latency neurodegenerative disease in the western Pacific region.
PubMed: Dietary protein and chronic toxicity of 1,2-dimethylhydrazine fed to mice.
PubMed: Mutagenicity of methylazoxymethanol acetate in the presence of alcohol dehydrogenase, aldehyde dehydrogenase, and rat liver microsomes in Salmonella typhimurium His G46.
PubMed: Intestinal microflora: metabolism of drugs and carcinogens.
PubMed: Etiology of Alzheimer's disease: a western pacific view.
PubMed: Acquired chemical defense in the lycaenid butterfly,Eumaeus atala.
PubMed: Mutagenic activity of promutagens in plants: indirect evidence of their activation.
PubMed: A poison tree.
PubMed: Statistical analysis of a carcinogen mixture experiment. I. Liver carcinogens.
PubMed: Hepatic and spinal lesions in goats chronically intoxicated with cycasin.
PubMed: On the distribution of genotoxic factors in various organs of mice treated with cycasin.
PubMed: Induction of tumors with cycasin in newborn and preweanling rats.
PubMed: Animal model for colorectal cancer.
PubMed: Diet and nutrition as risk factors for cancer.
PubMed: [Experimental multiple primary malignant tumors induced by chemical carcinogen].
PubMed: Review: putative mutagens and carcinogens in foods. V. Cycad azoxyglycosides.
PubMed: Potentiation of large intestinal tumorigenicity of cycasin derivative by high-fat diet and Lactobacillus in germfree mice.
PubMed: Activation of cycasin to a mutagen for Saccharomyces cerevisiae by rat intestinal flora.
PubMed: Bacterial mutagenicity of natural materials, pyrolysis products and additives in foodstuffs and their association with genotoxic effects in mammals.
PubMed: Cycasin and its mutagenic metabolites.
PubMed: Genetic damage caused by methylazoxymethanol acetate, the aglycone of cycasin. Analysis of sister-chromatid exchange frequency under in vivo conditions and in cell cultures.
PubMed: Comparison of the carcinogenicity of methylazoxymethanol-beta-D-glucosiduronic acid in conventional and germfree Sprague-Dawley rats.
PubMed: Determination of the carcinogen methylazoxymethyl-beta-D-glucosiduronic acid in rat bile and urine.
PubMed: Natural carcinogenic products of plant origin.
PubMed: [Occurrence of neoplasms in the large intestine and role of intestinal bacteria].
PubMed: Genotoxicity of cycasin in the hepatocyte primary culture/DNA repair test supplemented with beta-glucosidase.
PubMed: Rapid hepatoma induction in rats by dipentylnitrosamine and its modification by other carcinogens.
PubMed: Effect of phenobarbital on the development of neoplastic lesions in the liver of cycasin-treated rats.
PubMed: [Classification, histochemistry and ultrastructure of experimental renal tumors (author's transl)].
PubMed: Carcinogenicity and hepatotoxicity of cycasin and its aglycone methylazoxymethanol acetate in nonhuman primates.
PubMed: Role of bacteria in human carcinogenesis.
PubMed: Mutagenicity of the naturally occurring carcinogen cycasin and synthetic methylazoxymethanol conjugates in Salmonella typhimurium.
PubMed: Synthesis of the glucuronic acid conjugate of methylazoxymethanol.
PubMed: DNA fragmentation in some organs of rats and mice treated with cycasin.
PubMed: Mutagenicity of alkaloids in the Salmonella/microsome system.
PubMed: Contributions of gnotobiology to nutrition science.
PubMed: Toxins and carcinogens in the environment: an observation in the tropics.
PubMed: A practical procedure for testing DNA damage in vivo, proposed for a pre-screening of chemical carcinogens.
PubMed: [Histology, fine structure and differentiation of experimental Wilms tumors (author's transl)].
PubMed: Naturally occurring compounds Containing a nitrogen-nitrogen bond.
PubMed: Cancer and the environment.
PubMed: Effect of coffee on carcinogenicity of cycasin.
PubMed: PHA response and methylazoxymethanol acetate.
PubMed: Pathogenesis of methylazoxymethanol-induced lesions in the postnatal mouse cerebellum.
PubMed: Carcinogens occurring naturally in foods.
PubMed: Leiomyomas and leiomyosarcomas of the kidney in 4-day-old BUF rats given methylazoxymethanol acetate intraperitoneally.
PubMed: Naturally occuring mutagens.
PubMed: Cycasin.
PubMed: Experimental carcinogenesis in small aquarium fishes.
PubMed: [Microorganisms as indicators of the mutagenic activity of chemical compounds and their metabolites].
PubMed: Intestinal tumors of rats by gastric or intestinal administration of cycad extract and cycasin.
PubMed: Hepatic tumors of rabbits induced by cycad extract.
PubMed: Dendritic growth in vitro.
PubMed: [Ultrastructure of cycasin-induced adenomas of kidney (author's transl)].
PubMed: Renal carcinogenesis.
PubMed: The alkylation of nucleic acids of rat and mouse in vivo by the carcinogen 1,2-dimethylhydrazine.
PubMed: Morphological and biochemical effects of 1,2-dimethylhydrazine and 1-methylhydrazine in rats and mice.
PubMed: [Cycasin carcinogenesis. (5). Carcinogenic properties of cycasin, methylazoxymethanol and methylazoxymethyl benzoate].
PubMed: Acute hepatic lesions induced by cycasin.
PubMed: Induction of a retinal disorder with cycasin in newborn mice and rats.
PubMed: Relations between postnatal days of mice and carcinogenic effect of cycasin.
PubMed: High yield of hepatic tumors in rats by cycasin.
PubMed: Cycasin-induced central nervous system lesions in postnatal mice.
PubMed: Fine structure of cycasin-induced cerebellar alterations.
PubMed: Cycasin in cycad materials used in Japan.
PubMed: Lipid composition of the cerebellum and spinal cord in postnatal cycasin-treated Swiss albino mice: preliminary observations.
PubMed: Carcinogenicity and neurotoxicity of cycasin with sepcial reference to species differences.
PubMed: -Glucosidase modulation in preweanling rats and its association with tumor induction by cycasin.
PubMed: [Natural carcinogens: target organs and species specificity in induction of cancer by single administration of cycasin].
PubMed: [Natural carcinogens: aglycon-methylazoxymethanol in cycasin].
PubMed: [Natural carcinogens: isolation of cycasin].
PubMed: [Natural carcinogens: toxicity and carcinogenicity of cyasin: induction of tumors by cycasin in the seeds of Cycas revoluta].
PubMed: [Natural carcinogens: hepatic disorders in the rat caused by cycasin, with special reference to the induction of hepatic tumors].
PubMed: Decomposition of methylazoxymethanol, the aglycone of cycasin, in D 2 O.
PubMed: An electron microscopic study of cycasin-induced cerebellar alterations.
PubMed: Shift of target organs in cycasin carcinogenesis.
PubMed: Dose related effects of cycasin induced renal and hepatic tumors.
PubMed: Carcinogenic effects of cycasin in Syrian golden hamsters and the transplantability of induced tumors.
PubMed: High incidence of pulmonary tumors in dd mice by a single injection of cycasin.
PubMed: [Carcinogenesis by cycasin, with special reference to the target organs].
PubMed: Tumor induction in C57BL-6 mice by a single administration of cycasin.
PubMed: Induction of a cerebellar disorder with cycasin in newborn mice and hamsters.
PubMed: Cycling of cycasin from newborn rats to their mother and back to the newborn.
PubMed: Cycasin: detection of associated mutagenic activity in vivo.
PubMed: [Cycasin-induced renal tumors in the Wistar rat with special consideration of the adenoma].
PubMed: Toxicology of cycasin.
PubMed: Toxicology of cycasin.
PubMed: Effect of cycasin on protein synthesis.
PubMed: Induction of mammary cancer in rats with cycasin: a preliminary report.
PubMed: Tumor induction in Fischer and Osborne-Mendel rats by a single administration of cycasin.
PubMed: Transplantability of cycasin-induced tumors in rats, with emphasis on nephroblastomas.
PubMed: Evidence for transplacental passage of the natural carcinogen cycasin and its aglycone.
PubMed: Induction of a neurological disorder by cycasin in mice.
PubMed: Similarities between the biochemical actions of cycasin and dimethylnitrosamine.
PubMed: Tumor induction in germfree rats with methylazoxymethanol (MAM) and synthetic MAM acetate.
PubMed: Mutation in Drosophila by methylazoxymethanol, the aglycone of cycasin.
PubMed: Cycasin synthesis in Seirarctia echo (Lepidoptera) larvae fed methylazoxymethanol.
PubMed: Role of intestinal microorganisms in determining cycasin toxicity.
PubMed: [Histological-histochemical studies on the "interstitial cycasin tumor" of rat kidneys].
PubMed: Mutagenicity of cycasin aglycone (methylazoxymethanol), a naturally occurring carcinogen.
PubMed: Effect of boiling and storing on cycasin content of Cycas circinalis L.
PubMed: Studies on methylazoxymethanol, the aglycone of cycasin: methylation of nucleic acids in vitro.
PubMed: Cycasin excretion in conventional and germfree rats.
PubMed: Naturally occurring toxicants in foods.
PubMed: The induction of intestinal neoplasms in rats with the glycoside cycasin and its aglycone.
PubMed: CYCASIN: RADIOMIMETIC EFFECT.
PubMed: Cycasin content of Cycas circinalis.
PubMed: STUDIES ON METHYLAZOXYMETHANOL, THE AGLYCONE OF CYCASIN. ISOLATION, BIOLOGICAL, AND CHEMICAL PROPERTIES.
PubMed: STUDIES ON METHYLAZOXYMETHANOL, THE AGLYCONE OF CYCASIN: A SYNTHESIS OF METHYLAZOXYMETHYL ACETATE.
PubMed: RESPONSE OF LIVER NUCLEIC ACIDS AND LIPIDS IN RATS FED CYCAS CIRCINALIS L. ENDOSPERM OR CYCASIN.
PubMed: EFFECT OF INGESTED CYCASIN ON RAT BLOOD PLASMA CHOLINESTERASE.
PubMed: CARCINOGENIC EFFECTS OF CYCAD MEAL AND CYCASIN, METHYLAZOXYMETHANOL GLYCOSIDE, IN RATS AND EFFECTS OF CYCASIN IN GERMFREE RATS.
PubMed: EFFECTS OF CYCAD MEAL AND CYCASIN ON HISTOCHEMICALLY DEMONSTRABLE LIVER PHOSPHATASES AND NON SPECIFIC ESTERASES.
PubMed: RATES AND KINETICS OF CATALASE SYNTHESIS AND DESTRUCTION IN RATS FED CYCAD AND CYCASIN IN VIVO.
PubMed: EFFECT OF CYCAD AND CYCASIN FEEDING ON LIVER RNA, DNA, SUCCINIC OXIDASE, AND LIPIDS IN THE RAT.
PubMed: EFFECTS OF CYCASIN AND CYCAD MEAL.
PubMed: METHYLAZOXYMETHANOL, THE AGLYCONE OF CYCASIN.
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