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Cycasin

HCID 5459896
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Grundinformationen

CAS
14901-08-7
Standard-SMILES
C/[N+]([O-])=N/CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIKey
YHLRMABUJXBLCK-LBCXAKKBSA-N
Summenformel
C8H16N2O7
Durchschnittliche Molmasse
252,22 g/mol
Monoisotopische Masse
252,09575085

Überblick

Cycasin can cause cancer according to an independent committee of scientific and health experts.

Namen und Bezeichner

Bevorzugter Name
Cycasin
IUPAC
(Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium

Namen und Synonyme

CykazineCYCASINbeta-D-Glucosyloxyazoxymethanebeta-D-GlucosyloxyazoxymethaseCycas revoluta glucoside14901-08-7(Methyl-ONN-azoxy)methyl beta-D-glucopyranosideMethylazoxymethanol-beta-D-glucoside9H51HL0E1DMethylazoxymethanol glucosidebeta-D-Glucopyranoside, (methyl-ONN-azoxy)methylDTXSID2057574
Weitere Namen anzeigen
Methylazoxymethyl-b-D-glucopyranosideNSC-15190(Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azaniumCHEBI:17074(Z)-methyl-oxido-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethylimino)azanium(Z)-methyl-oxido-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxymethylimino)ammonium(Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethylimino]ammoniumRefChem:129164

Datenbank-Bezeichner

CAS
14901-08-7
PubChem CID
5459896
DTXSID
DTXSID2057574
UNII
9H51HL0E1D
Nikkaji
J3.130E

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-2,6
Polarare Oberfläche (TPSA)
140 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
4
Schwere Atome
17
Formalladung
0
Komplexität
275

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Plant Toxins
Color/Form · 2 Einträge

COLORLESS, LONG NEEDLES

NEEDLES FROM WATER + ACETONE + ETHER

SolubilityREADILY SOL IN WATER & DILUTE ETHANOL; INSOL IN BENZENE, CHLOROFORM, ETHYL ACETATE, ACETONE; SPARINGLY SOL IN ABSOLUTE ETHANOL
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Optical RotationSPECIFIC OPTICAL ROTATION: -44 DEG @ 18 °C/D (WATER, 0.62%); MAX ABSORPTION (0.4 MOLAR H2SO4): 217 NM
Physical DescriptionColorless solid; [HSDB]
Other Experimental Properties · 2 Einträge

DECOMPOSES @ 154 °C

EASILY HYDROLYZED, ESP UNDER ALKALINE CONDITIONS

Sicherheit und Regulatorisches

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Gefahrenhinweise

Regulatory InformationHazard Traits - Carcinogenicity; Other Toxicological Hazard Traits
Hazards SummaryCarcinogenic in mice, rats, hamsters, guinea pigs, rabbits, and fish producing malignant tumors mainly of the liver, kidney, and intestine; [IARC]
Special Reports · 1 Eintrag

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Cycasin (14901-08-7) is delisted as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/append/appb.pdf]

Shipment Methods and Regulations · 2 Einträge

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

FOLLOWING ITS ORAL ADMIN TO RATS, CYCASIN IS SPLIT BY BETA-GLUCOSIDASE OF BACTERIAL FLORA TO FORM METHYLAZOXYMETHANOL.

ENZYMATIC HYDROLYSIS /OF CYCASIN/ TO METHYLAZOXYMETHANOL ALSO OCCURS IN SC TISSUES OF NEWBORN MICE & RATS, WHICH IN EARLY POSTNATAL PERIOD CONTAIN A GLUCOSIDASE THAT DISAPPEARS AFTER 14TH-25TH DAY OF LIFE.

MeSH Pharmacological Classification · 2 Einträge

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Toxic substances from microorganisms, plants or animals that interfere with the functions of the nervous system. Most venoms contain neurotoxic substances. Myotoxins are included in this concept.

Absorption, Distribution and Excretion · 2 Einträge

CYCASIN & METHYLAZOXYMETHANOL /METABOLITE OF CYCASIN/ CROSS PLACENTA IN RATS & HAMSTERS...

FOLLOWING ORAL ADMIN...TO CONVENTIONAL & GERM-FREE RATS ONLY 24%...RECOVERED IN URINE & FECES OF CONVENTIONAL RATS...100% IN...GERM-FREE RATS. IN RATS GIVEN 45-50 MG/ANIMAL BY STOMACH TUBE, 30-63% OF ADMIN DOSE WAS RECOVERED IN URINE. FOLLOWING IP INJECTION...IN RATS, 95-100%...RECOVERED FROM URINE WITHIN 24 HR.

Verwendung und Herstellung

Uses · 3 Einträge

Toxin derived from seeds of Cycus revoluta and other plants; [Merck Index] No commercial use in the US; Has been used as a food by Aboriginal groups in northern Australia; Soaking plant in water before consumption reduces its toxicity; The metabolite methylazoxymethanol, a biological methylating agent, is the active carcinogen; [HSDB]

NOT USED COMMERCIALLY IN USA

CYCADS HAVE BEEN USED FOR VARIOUS MEDICINAL PURPOSES & ALSO AS HUMAN FOOD. /CYCADS/

U.S. Production · 2 Einträge

(1977) NOT PRODUCED COMMERCIALLY IN US

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Sicherheit und Schutzausrüstung

Storage Conditions · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Cleanup Methods · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Disposal Methods · 5 Einträge

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for CYCASIN (6 total), please visit the HSDB record page.

Preventive Measures · 5 Einträge

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for CYCASIN (9 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

Toxikologische Informationen

Interactions...FOUND, USING A HOST-MEDIATED ASSAY, THAT PRIOR TREATMENT OF SWISS MICE WITH AMPICILLIN, WHICH REDUCES ENTERIC BACTERIA POPULATION, ABOLISHED MUTAGENICITY TO SALMONELLA TYPHIMURIUM G-46.
Adverse EffectsIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Medical Surveillance · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

Natural Pollution SourcesCYCASIN OCCURS IN SEEDS, ROOTS & LEAVES OF CYCAD PLANTS (FAMILY CYCADACEAE) WHICH ARE FOUND IN TROPICAL & SUBTROPICAL REGIONS OF WORLD. AMT OF CYCASIN PRESENT IN CYCAD NUTS DEPENDS ON SPECIES...
Human Toxicity Excerpts · 4 Einträge

DURING 1959 NATIVES OF MIYAKO ISLANDS, OKINAWA, SUBSISTED MAINLY ON CYCADS. CANCER MORTALITY &...HEPATOMA MORTALITY IN THESE ISLANDS BETWEEN 1961 & 1966 DID NOT DIFFER SIGNIFICANTLY FROM THAT IN INTERIOR OF JAPAN & DID NOT INCR APPRECIABLY OVER THAT PERIOD. /CYCADS/

A CARCINOGEN OF WHICH AGLYCONE, METHYLAZOXYMETHANOL, IS ACTIVE COMPONENT...

Despite the known human ingestion of cycad nuts; evidence that cycasin causes human liver disease has been scant, perhaps because the populations that eat the cycad nut have learned to process the fruit in a manner that removes the toxin. Nevertheless; a recent report from Japan described a small epidemic of acute hepatic injury attributable to the ingestion of cycad nuts, and this toxic plant warrants being included among the domestic hepatotoxins.

Exposure to cycad seed kernel is an etiologic factor for the western Pacific amyotrophic lateral sclerosis and parkinsonism-dementia complex. Traditionally processed cycad flours (n = 17) obtained from Chamorro residents of Guam and the adjacent island of Rota at risk for neurodegenerative disease were extracted and analyzed by high-performance liquld chromatography for content of beta-N-methylamino-L-alanine and methyl-azoxymethanol beta-D-glucoside (cycasin). Cycasin (detection limit: picomole) was present in concentrations of 0.004 to 75.93 ug/g (mean, 12.45 + or - 5.0 ug/g) and levels of beta-N-methylamino-L-alanine (detection limit: subpicomole) ranged from 0.00 to 18.39 ug/g (mean 5.44 + or - 1.56 ug/g). On average, cycasin content was approximately 10 times higher than that of beta-N-methylamino-L-alanine. The largest concentrations of cycasin were found in samples from villages with a high reported prevalence of amyotrophic lateral sclerosis/parkinsonism-dementia complex. Ingestion of cycad-derived food would result in estimated human exposure to milligram amounts of cycasin per day. The cytotoxic properties of cycasin merit consideration in relation to the etiology of western Pacific amyotrophic lateral sclerosis/parkinsonism-dementia complex.

Carcinogen Classification · 5 Einträge

Cycasin

Group 2B: Possibly carcinogenic to humans

Volume 10: (1976) Some Naturally Occurring Substances

1987

1987

Non-Human Toxicity Excerpts · 5 Einträge

HIGH INCIDENCE OF LIVER TUMORS...HEPATOMAS & SARCOMAS...OBSERVED IN 62/73 SPRAGUE-DAWLEY RATS OF BOTH SEXES ADMIN CYCASIN IN DRINKING WATER FOR LIFE (AVG INTAKE, 10 MG/KG BODY WT/DAY). LUNG METASTASES OF HEPATOMAS WERE OBSERVED IN 9/35 CASES; 16 KIDNEY TUMORS (9 NEPHROBLASTOMAS & 7 ADENOCARCINOMAS) WERE ALSO OBSERVED...

...SINGLE-DOSE EXPT IN WEANLING OSBORNE-MENDEL RATS GIVEN CYCASIN BY STOMACH TUBE, TUMORS OF KIDNEY, INTESTINE, LIVER, LUNG & BRAIN (IN...ORDER OF FREQUENCY...IN ANIMALS THAT SURVIVED 6 MO OR MORE. TUMOR INCIDENCES...4/13 @ 100 MG/KG...13/13 @ 250 MG/KG...6/6 @ 500 MG/KG...0/1 @ 750 MG/KG...2/3 @ 1000 MG/KG BODY WT...

...2-MO-OLD HAMSTERS...SINGLE DOSES...0.15 OR 0.1 MG/G BODY WT CYCASIN BY STOMACH TUBE. ...41 ANIMALS...SURVIVED MORE THAN 150 DAYS, 23 TUMORS...2 LIVER-CELL ADENOMAS, 7 BILE-DUCT CARCINOMAS, 1 HEMANGIOENDOTHELIAL SARCOMA, 5 LUNG ADENOMAS, 4 INTESTINAL TUMORS, 1 KIDNEY CARCINOMA & 3 MALIGNANT LYMPHOMAS.

...IP OR IV INJECTIONS...20 MG/KG BODY WT METHYLAZOXYMETHANOL /METABOLITE OF CYCASIN/ TO FISCHER RATS ON DAYS 14-16 OR 20-21 OF PREGNANCY, GLIOMAS, PULMONARY ADENOMAS, BENIGN TUMORS OF JEJUNUM, COLON & RECTUM, SARCOMAS OF KIDNEY & TRANSITIONAL CELL-CARCINOMA OF KIDNEY WERE OBSERVED IN OFFSPRING.

For more Non-Human Toxicity Excerpts (Complete) data for CYCASIN (22 total), please visit the HSDB record page.

Evidence for Carcinogenicity · 2 Einträge

No data are available in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans.

Cycasin: delisted as reasonably anticipated to be a human carcinogen.

Non-Human Toxicity Values · 2 Einträge

LD50 Rat oral 270 mg/kg

LD50 Mouse oral 500 mg/kg

(1979) NOT PRODUCED COMMERCIALLY IN US

Methods of ManufacturingTOXIC SUBSTANCE FROM SEEDS OF CYCAS REVOLUTA THUMB & C CIRCINALIS L, CYCADACEAE FROM GUAM.
General Manufacturing Information · 4 Einträge

CYCAD STARCH FROM NUTS OF CYCAS CIRCINALIS & CYCAS REVOLUTA IS USED IN MARIANA ISLANDS, ON RYUKYU ISLANDS (JAPAN) & IN INDOCHINA, INDIA & AFRICA. IN THESE SAME AREAS THE SEEDS ARE ALSO PREPARED FOR USE BOTH AS EXTERNAL & INTERNAL MEDICINES. BIOL ACTIVE PART...IS ITS AGLYCONE, METHYLAZOXYMETHANOL...

...TOXIC & CARCINOGENIC ACTIVITY ARISES FROM AGLYCONE METHYLAZOXYMETHANOL WHICH IS RELEASED BY ACTION OF ENZYME BETA-GLUCOSIDASE DERIVED MAINLY FROM INTESTINAL MICROORGANISMS. CARCINOGENIC ENTITY MAY BE METABOLIC OXIDN PRODUCT, METHYLAZOXYFORMALDEHYDE. /CYCASIN & CONGENERS, MACROSAMIN, NEOCYCASIN/

CYCADS HAVE BEEN USED FOR VARIOUS MEDICINAL PURPOSES & ALSO AS HUMAN FOOD. THEIR TOXIC PROPERTIES HAVE BEEN LONG RECOGNIZED & ARE REDUCED BY SOAKING PLANT MATERIAL IN WATER BEFORE CONSUMPTION. /CYCADS/

The seeds of cycad plants are a toxic food used by many Aboriginal groups in northern Australia. Acute symptoms produced after consumption of untreated Cycas seeds are due to azoxyglycosides, especially cycasin, although the toxic dose depends on the animal species tested. There are three traditional methods used to treat these seeds: brief leaching in water; prolonged leaching in water; and aging. Aboriginal people living at Donydii outstation in northeast Arnhem Land, most regularly consume aged seeds of Cycas angulata R.Br. Analyses of fresh seeds and seeds prepared at Donydji and in the laboratory indicate that cycasin is effectively removed by all the traditional preparation techniques, although each technique has an end product with different storage and handling properties. The social implications of processing need further elaboration but these techniques have a long history and archaeological remains of seeds in Australia may date back to the Pleistocene.