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methyl isothiocyanate
methylimino-sulfanylidenemethane

Supplier Sponsors

Name:methylimino-sulfanylidenemethane
CAS Number: 556-61-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-132-5
FDA UNII:RWE2M5YDW1
Nikkaji Web:J3.295F
Beilstein Number:0605319
MDL:MFCD00004818
XlogP3:0.90 (est)
Molecular Weight:73.11791000
Formula:C2 H3 N S
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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JECFA Food Flavoring:1884 methyl isothiocyanate
FEMA Number:4426 methyl isothiocyanate
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: METHYL ISOTHIOCYANATE
 
Physical Properties:
Appearance:colorless white to orange tan clear liquid to solid (est)
Assay: 96.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.93800 to 0.94200 @ 25.00 °C.
Pounds per Gallon - (est).: 7.805 to 7.838
Refractive Index:1.49500 to 1.49900 @ 20.00 °C.
Melting Point: 34.00 to 36.00 °C. @ 760.00 mm Hg
Boiling Point: 117.00 to 118.00 °C. @ 760.00 mm Hg
Vapor Pressure:31.184999 mm/Hg @ 25.00 °C. (est)
Flash Point: 90.00 °F. TCC ( 32.22 °C. )
logP (o/w): 0.940
Soluble in:
 alcohol
 water, 7600 mg/L @ 20 °C (exp)
Insoluble in:
 water
Similar Items:note
allyl isothiocyanate
amyl isothiocyanate
isoamyl isothiocyanate
benzyl isothiocyanate
3-buten-1-yl isothiocyanate
butyl isothiocyanate
isobutyl isothiocyanate
sec-butyl isothiocyanate
ethyl isothiocyanate
5-hexen-1-yl isothiocyanate
hexyl isothiocyanate
4-methyl thiobutyl isothiocyanate
6-methyl thiohexyl isothiocyanate
5-methyl thiopentyl isothiocyanate
4-pentenyl isothiocyanate
2-phenethyl isothiocyanate
isopropyl isothiocyanate
radish isothiocyanate
 
Organoleptic Properties:
Odor Type: pungent
Odor Strength:very high ,
recommend smelling in a 0.01 % solution or less
pungent mustard horseradish
Odor Description:at 0.01 % in propylene glycol. pungent mustard horseradish
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
methylimino-sulfanylidenemethane >98.0%(GC)
Penta International
METHYL ISOTHIOCYANATE
Sigma-Aldrich: Aldrich
For experimental / research use only.
Methyl Isothiocyanate 97%
TCI AMERICA
For experimental / research use only.
Methyl Isothiocyanate >98.0%(GC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
T N - Toxic, Dangerous for the environment.
R 23/25 - Toxic by inhalation and if swallowed.
R 34 - Causes burns.
R 43 - May cause sensitisation by skin contact.
R 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S 01/02 - Keep locked up and out of the reach of children.
S 36/37 - Wear suitable protective clothing and gloves.
S 38 - In case of insufficient ventlation, wear suitable respiratory equipment.
S 45 - In case of accident or if you feel unwell seek medical advice immediately.
S 60 - This material and its container must be disposed of as hazardous waste.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
 
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-rat LD50 [sex: M] 175 mg/kg

oral-rat LD50 [sex: F] 72 mg/kg

oral-mouse LD50 [sex: M] 90 mg/kg

oral-mouse LD50 [sex: F] 104 mg/kg

oral-duck LD50 136 mg/kg
Pesticide Manual. Vol. 9, Pg. 581, 1991.

intraperitoneal-mouse LD50 82 mg/kg
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

oral-mouse LD50 90 mg/kg
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

intraperitoneal-rat LD50 54 mg/kg
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

oral-rat LD50 72 mg/kg
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

Dermal Toxicity:
skin-rabbit LD50 33 mg/kg
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

skin-rat LD50 2780 mg/kg
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

skin-mouse LD50 1820 mg/kg
"Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.

subcutaneous-mouse LD50 50 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 505, 1955.

skin-rabbit LD50 33 mg/kg
Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.

skin-rat LD50 2780 mg/kg
"Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.

subcutaneous-rat LD50 59 mg/kg
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

Inhalation Toxicity:
inhalation-mouse LCLo 75 mg/m3/4H
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(5), Pg. 33, 1969.

inhalation-rat LC50 1900 mg/m3/1H
Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 297, 1990.

 
Safety in Use Information:
Category: flavoring agents
Recommendation for methyl isothiocyanate usage levels up to:
 not for fragrance use.
 
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 23
 average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: 0.050000.25000
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 0.250002.00000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.100000.50000
snack foods: 0.050000.25000
soft candy: --
soups: 0.050000.25000
sugar substitutes: --
sweet sauces: --
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Reasoned opinion on the modification of the existing maximum residue levels (MRLs) for dazomet in several vegetables
View page or View pdf

EPI System: View
NLM Hazardous Substances Data Bank:Search
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):556-61-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11167
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2477
WGK Germany:3
methylimino-sulfanylidenemethane
Chemidplus:0000556616
EPA/NOAA CAMEO:hazardous materials
RTECS:PA9625000 for cas# 556-61-6
 
References:
 methylimino-sulfanylidenemethane
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:556-61-6
Pubchem (cid):11167
Pubchem (sid):134976878
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C18587
HMDB (The Human Metabolome Database):HMDB34106
FooDB:FDB012372
Export Tariff Code:2930.90.5050
Haz-Map:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
Formulations/Preparations:
•usepaopp pesticide code 068103; trade names: trapex, vorlex, component of (with 029001 and 029002), biomet 33. •mitc is formulated as a solidified-melt, where it is a solid at ambient conditions and melts and vaporizes at elevated temperatures found within the pole being treated. •methylisothiocyanate (mitc) (mlpc international): methyl isothiocyanate 97%. •technical grade is greater than 94.5% pure •emulsifiable concentrate •mitc-fume •96% active in aluminum vials.
 
Potential Blenders and core components note
For Odor
fruity
furfuryl acetate
FL/FR
green
green dioxolane
FR
(Z)-3-
hexen-1-yl tiglate
FL/FR
1-
penten-3-ol
FL/FR
sulfurous
dimethyl sulfide
FL/FR
2-
methyl 5-(methyl thio) furan
FL/FR
2-
phenethyl isothiocyanate
FL/FR
For Flavor
No flavor group found for these
4-
methyl thiobutyl isothiocyanate
FL
6-
methyl thiohexyl isothiocyanate
FL
5-
methyl thiopentyl isothiocyanate
FL
4-
pentenyl isothiocyanate
FL
2-
phenethyl isothiocyanate
FL/FR
alliaceous
alliaceous
benzyl mercaptan
FL
cyclopentyl mercaptan
FL
3-
mercapto-2-pentanone
FL
burnt
methyl phenyl disulfide
FL
estery
furfuryl acetate
FL/FR
green
2-
furyl acetone
FL
(Z)-3-
hexen-1-yl tiglate
FL/FR
1-
penten-3-ol
FL/FR
musty
2-
methyl 5-(methyl thio) furan
FL/FR
onion
methyl propyl disulfide
FL
sulfurous
allyl sulfide
FL
dimethyl sulfide
FL/FR
furfuryl methyl sulfide
FL
vegetable
radish isothiocyanate
FL
 
Potential Uses:
FLwasabi
 
Occurrence (nature, food, other):note
 horseradish root
Search Trop Picture
 mustard oil
Search PMC Picture
 
Synonyms:
 biomet 33
 methane, (methylimino)thioxo-
 methane, isothiocyanato-
 methane,isothiocyanato-
 methyl mustard
 methyl mustard oil
 methylimino-sulfanylidenemethane
(methylimino)(thioxo)methane
 methylisothiocyanate
isothiocyanatomethane
isothiocyanic acid methyl ester
isothiocyanic acid, methyl ester
 trapex
 trapexide
 vorlex
 

Articles:

PubMed:Determination of methyl isocyanate in outdoor residential air near metam-sodium soil fumigations.
PubMed:Structural dynamics of phenylisothiocyanate in the light-absorbing excited states: resonance Raman and complete active space self-consistent field calculation study.
PubMed:Residential agricultural pesticide exposures and risk of neural tube defects and orofacial clefts among offspring in the San Joaquin Valley of California.
PubMed:Gas-phase reaction of methyl isothiocyanate and methyl isocyanate with hydroxyl radicals under static relative rate conditions.
PubMed:Community air monitoring for pesticides. Part 3: using health-based screening levels to evaluate results collected for a year.
PubMed:Water and methyl isothiocyanate distribution in soil after drip fumigation.
PubMed:Reduction of methyl isothiocyanate atmospheric emissions after application of metam sodium by shank injection.
PubMed:Dissipation of soil fumigants from soil following repeated applications.
PubMed:Pesticides exposure assessment of kettleman city using the industrial source complex short-term model version 3.
PubMed:Comparison of field methyl isothiocyanate flux following Pacific Northwest surface-applied and ground-incorporated fumigation practices.
PubMed:Nematicidal activity of 2-thiophenecarboxaldehyde and methylisothiocyanate from caper (Capparis spinosa) against Meloidogyne incognita.
PubMed:Fixation of carbon dioxide and related small molecules by a bifunctional frustrated pyrazolylborane Lewis pair.
PubMed:Allergic contact dermatitis due to dazomet absorbed by agricultural rubber boots.
PubMed:Ethyl formate plus methyl isothiocyanate--a potential liquid fumigant for stored grains.
PubMed:Metam sodium intoxication: the specific role of degradation products--methyl isothiocyanate and carbon disulphide--as a function of exposure.
PubMed:Infrared emission following photolysis of methylisothiocyanate and methylthiocyanate.
PubMed:Recent studies of measures to improve basamid soil disinfestation.
PubMed:Absolute kinetics and reaction efficiencies of hydroxyl-radical-induced degradation of methyl isothiocyanate (MITC) in different quality waters.
PubMed:Human chemosensory perception of methyl isothiocyanate: chemesthesis and odor.
PubMed:Complexes of Gilman reagents with C-S and C-N double bonds: sigma or pi bonding?
PubMed:Testing of a new disinfectant process for poultry viruses.
PubMed:Dose response assessment for effects of acute exposure to methyl isothiocyanate (MITC).
PubMed:Surface water seal application to minimize volatilization loss of methyl isothiocyanate from soil columns.
PubMed:Microbial aspects of accelerated degradation of metam sodium in soil.
PubMed:Excessive longitudinal FEV1 decline and risks to future health: a case-control study.
PubMed:Accelerated degradation of metam-sodium in soil and consequences for root-disease management.
PubMed:Combinations of soil fumigants for methyl-bromide replacement.
PubMed:Status of chemical alternatives to methyl bromide for pre-plant fumigation of soil.
PubMed:Determination of methyl isothiocyanate in air downwind of fields treated with metam-sodium by subsurface drip irrigation.
PubMed:Fumigation of wheat using liquid ethyl formate plus methyl isothiocyanate in 50-tonne farm bins.
PubMed:Optimization of metam sodium application by rotary spading injection.
PubMed:Combinations of reduced rates of 1,3-dichloropropene and dazomet as a broad spectrum soil fumigation strategy in view of methyl bromide replacement.
PubMed:Method development study for APR cartridge evaluation in fire overhaul exposures.
PubMed:Distribution and efficacy of drip-applied metam-sodium against the survival of Rhizoctonia solani and yellow nutsedge in plastic-mulched sandy soil beds.
PubMed:Methyl isothiocyanate residential community air assessment for South Franklin County, Washington.
PubMed:Emission, distribution and leaching of methyl isothiocyanate and chloropicrin under different surface containments.
PubMed:Illnesses related to shank application of metam-sodium, Arvin, California, July 2002.
PubMed:Evaluation of volatile low molecular weight insecticides using Drosophila melanogaster as a model.
PubMed:Modeling methyl isothiocyanate soil flux and emission ratio from a field following a chemigation of metam-sodium.
PubMed:Effects of application methods of metam sodium and plastic covers on horizontal and vertical distributions of methyl isothiocyanate in bedded field plots.
PubMed:Fumigant distribution in forest nursery soils under water seal and plastic film after application of dazomet, metam-sodium and chloropicrin.
PubMed:Physical, chemical and environmental properties of selected chemical alternatives for the pre-plant use of methyl bromide as soil fumigant.
PubMed:Ab initio computational insight into the ion-pair S(N)2 reaction of lithium isothiocyanate and methyl fluoride in the gas phase and in acetone solution.
PubMed:The enantioseparation of amino acids on a teicoplanin chiral stationary phase using non-aqueous mobile phases after pre-column derivatization with sulfur-containing reagents: the considerations of mobile phase composition and analyte structure variation on resolution enhancement.
PubMed:Degradation of methyl isothiocyanate and chloropicrin in forest nursery soils.
PubMed:The crucial role of calcium interacting with soil pH in enhanced biodegradation of metam-sodium.
PubMed:Biofumigation: environmental impacts on the biological activity of diverse pure and plant-derived isothiocyanates.
PubMed:[Determination of isothiocyanates in human urine by high performance liquid chromatography].
PubMed:Application of solid phase microextraction for the determination of soil fumigants in water and soil samples.
PubMed:Effect of application variables on emissions and distribution of fumigants applied via subsurface drip irrigation.
PubMed:Effect of combined application of methyl isothiocyanate and chloropicrin on their transformation.
PubMed:Effect of surface tarp on emissions and distribution of drip-applied fumigants.
PubMed:Modeling of methyl isothiocyanate air concentrations associated with community illnesses following a metam-sodium sprinkler application.
PubMed:Developmental toxicity of the dithiocarbamate pesticide sodium metam in zebrafish.
PubMed:Leaching potential of persistent soil fumigant residues.
PubMed:[Synthesis and nNOS inhibitory activity of benzenealkyl isothiourea compounds].
PubMed:Formation and extraction of persistent fumigant residues in soils.
PubMed:Behavior of methyl isothiocyanate in soils under field conditions in Morocco.
PubMed:Behavior of 1,3-dichloropropene and methyl isothiocyanate in undisturbed soil columns.
PubMed:A two-dimensional model for simulating the transport and fate of toxic chemicals in a stratified reservoir.
PubMed:Community exposures to airborne agricultural pesticides in California: ranking of inhalation risks.
PubMed:Does the odor from sponges of the genus Ircinia protect them from fish predators?
PubMed:Identification of a new urinary metabolite of carbon disulfide using an improved method for the determination of 2-thioxothiazolidine-4-carboxylic acid.
PubMed:Determination of N-acetyl-S-(N-methylcarbamoyl)cysteine (AMCC) in the general population using gas chromatography-mass spectrometry.
PubMed:Degradation of soil fumigants as affected by initial concentration and temperature.
PubMed:Impact of fumigants on soil microbial communities.
PubMed:Exudation of low molecular weight compounds (thiobismethane, methyl isocyanide, and methyl isothiocyanate) as a possible chemical defense mechanism in the marine sponge Ircinia felix.
PubMed:Genotoxic effects of methyl isothiocyanate.
PubMed:Advantageous attributes of larval whitefringed weevil, Naupactus leucoloma (Coleoptera: Curculionidae) for bioassaying soil fumigants, and responses to pure and plant-derived isothiocyanates.
PubMed:The influence of metam sodium on soil respiration.
PubMed:Bactericidal activity of isothiocyanate against pathogens on fresh produce.
PubMed:Pesticide tests on humans cause concern.
PubMed:Reversible Insertion of Methyl Isothiocyanate into Copper(I) Aryloxides.
PubMed:Synthesis and Characterization of Rhenium(V) Oxo Complexes with a New Thiol-Amide-Thiourea Ligand System. X-ray Crystal Structure of [1-Phenyl-3-[2-((2-thioacetyl)amino)ethyl]thioureato]oxorhenium(V).
PubMed:Philip Morris cigarettes recall, May 1995-March 1996. From the Centers for Disease Control and Prevention.
PubMed:Role of decomposition products in sodium methyldithiocarbamate-induced immunotoxicity.
PubMed:Recall of Philip Morris cigarettes, May 1995-March 1996.
PubMed:S-methylation as a bioactivation mechanism for mono- and dithiocarbamate pesticides as aldehyde dehydrogenase inhibitors.
PubMed:Analogues of disaccharides and glycosides containing a cyclic guanidinium structure show varying inhibitory effects on glycoside hydrolases.
PubMed:Gas phase photolysis of methyl isothiocyanate.
PubMed:Characterization of protein adducts produced by N-methyldithiocarbamate and N-methyldithiocarbamate esters.
PubMed:Possible side effects of airborne pesticides on fungi and vascular plants in The Netherlands.
PubMed:[Chemical modification of myoglobin by isothiocyanate reagents. The effect of modifying the N-terminal amino group on protein conformation].
PubMed:Analysis of methyl isothiocyanate in wine by gas chromatography with dual detection.
PubMed:Plant-natural enemy association in tritrophic system,Cotesia rubecula-Pieris rapae-brassicaceae (Cruciferae). III: Collection and identification of plant and frass volatiles.
PubMed:Persistent respiratory health effects after a metam sodium pesticide spill.
PubMed:Dose-response assessment of airborne methyl isothiocyanate (MITC) following a metam sodium spill.
PubMed:Quantum Yield for Production of CH3NC in the Photolysis of CH3NCS.
PubMed:Chemotaxis away from thiocyanic and isothiocyanic esters in Pseudomonas aeruginosa.
PubMed:Effects of fumigant nematicides on yield and quality of paste tomatoes grown in southwestern ontario.
PubMed:Methyl isothiocyanate in wine.
PubMed:Spring or Fall Fumigation for Control of Meloidogyne spp. on Tobacco.
PubMed:Soil fumigation: principles and application technology.
PubMed:Ethylene-like activity of isocyanides.
PubMed:Efficacy of Fumigant and Nonfurmigant Nematicides for Control of Meloidogyne arenaria on Peanut.
PubMed:Screening of a Granular Chelate of Metham-Zinc for Nematicidal Activity Using Citrus and Root-knot Nematodes.
PubMed:Determination of sodium N-methyldithiocarbamate (metham sodium) and methyl isothiocyanate in aqueous samples by high-performance liquid chromatography using a micellar mobile phase.
PubMed:Ultrastructural changes in the respiratory tract of rats following methyl isocyanate inhalation.
PubMed:The public health implications of the Bhopal disaster. Report to the Program Development Board, American Public Health Association. Bhopal Working Group.
PubMed:Methyl isocyanate subchronic vapor inhalation studies with Fischer 344 rats.
PubMed:A simple and reliable device for monitoring fumigant residues in soil.
PubMed:Control of Heterodera carotae, Ditylenchus dipsaci, and Meloidogyne javanica with Fumigant and Nonfumigant Nematicides.
PubMed:Effects of minute doses of ethylenebisdithiocarbamate disodium salt (nabam) and its degradative products on connective tissue envelopes of the notochord in Xenopus: an ultrastructural study.
PubMed:Effect of anion-specific inhibitors on the utilization of sugar nucleotides for N-linked carbohydrate unit assembly by thyroid endoplasmic reticulum vesicles.
PubMed:Metabolism of some naturally occurring isothiocyanates in the rat.
PubMed:Fatal poisoning with methyl isothiocyanate.
PubMed:Allergic contact dermatitis from methylisothiocyanate in soil disinfectants.
PubMed:Chemical Control of Nematodes and Soil-borne Plant-Pathogenic Fungi on Cabbage Tranplants.
PubMed:Gas-liquid chromatographic determination of methyl isothiocyanate in soils.
PubMed:Studies on the reaction of proteins and peptides with methyl isothiocyanate and identification of the methylthiohydantoins by gas-liquid chromatography.
PubMed:Amino acid sequence analysis with methyl isothiocyanate. Resolution of the methylthiohydantoins by gas-liquid partition chromatography.
 
Notes:
Isol. from mustard oil, present as glucoside (Methyl glucosinolate LBB66-Y)
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