70-25-7

Basic information

• Product Name: 1-Methyl-3-nitro-1-nitrosoguanidine
• Synonyms: Diazomethane precursor, MNNG, N-Methyl-Nμ-nitro-N-nitrosoguanidine;1-Methyl-2-nitro-1-nitrosoguanidine;1-Methyl-3-nitro-1-nitrosoguanidine (wetted with ca. 50% Water, containing 5g on a dry weight basis);N-METHYL-n,n'-NITROSOGUANIDINE;N-Methyl-N'-nitro-N-nitrosoguanidine ,97%;N-METHYL-N'-NITRO-N-NITROSOGUANIDINE, MO ISTENED WITH WATER;3-Methyl-1-nitro-3-nitrosoguanidine;(wetted with ca. 50% Water, containing 5g on a dry weight basis)
• CAS NO: 70-25-7
• Molecular Formula: C₂H₅N₅O₃
• Molecular Weight: 147.09
• EINECS: 200-730-1
• Product Categories: Esterification & Alkylation (GC Derivatizing Reagents);GC Derivatizing Reagents;Mutagenesis Research Chemicals;Diazomethane Precursors & Equivalents (GC Derivatizing Reagents);Analytical Chemistry
• Mol File: 70-25-7.mol

Chemical Properties

• Melting Point: 118°C (dec.)
• Boiling Point: 267.16°C (rough estimate)
• Appearance: /
• Density: 1.7979 (rough estimate)
• Refractive Index: 1.6410 (estimate)
• Storage Temp.: 0-6°C
• Solubility: almost transparency in hot Methanol
• PKA: 3.09±0.50(Predicted)
• Water Solubility: Reacts violently
• Stability: Unstable. Reacts violently with water. May detonate under impact. Heat, light and moisture sensitive. May explode if stored in s
• Merck: 14,6103
• CAS DataBase Reference: 1-Methyl-3-nitro-1-nitrosoguanidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-nitro-1-nitrosoguanidine(70-25-7)
• EPA Substance Registry System: 1-Methyl-3-nitro-1-nitrosoguanidine(70-25-7)

Safety Data

• Hazard Codes: T;N,N,T
• Statements: 45-20-36/38-51/53
• Safety Statements: 53-45-61
• RIDADR: 2926
• RTECS: MF4200000
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 70-25-7(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
1-Methyl-3-nitro-1-nitrosoguanidine is used as a positive control in SHE cell transformation assays, which are crucial for studying the mechanisms of cell transformation and the effects of various agents on cellular processes.
Used in Chemical Synthesis:
In the past, 1-Methyl-3-nitro-1-nitrosoguanidine was also utilized in the preparation of diazomethane, an important reagent in organic chemistry for the methylation of various compounds.
Used in Toxicology and Mutagenesis Studies:
Due to its mutagenic and carcinogenic properties, 1-Methyl-3-nitro-1-nitrosoguanidine is employed in toxicology and mutagenesis research to investigate the effects of genotoxic agents on DNA and the subsequent development of cancer.

Production Methods

MNNG is one of the first chemical mutagens and is a stabilized form of methylnitrosoguanidine, which has not been isolated. It does not occur in nature, and human exposure to it is limited to laboratories.

Air & Water Reactions

Highly flammable. Reacts violently with water .

Reactivity Profile

1-Methyl-3-nitro-1-nitrosoguanidine will detonate under high impact. 1-Methyl-3-nitro-1-nitrosoguanidine is sensitive to heat. A sample has exploded when melted in a sealed capillary tube. Incompatible with acids, bases, oxidizing agents and reducing agents. Reacts with bases to release highly toxic, irritating and explosive gases. Reacts slowly with acids to release nitrous acid. Reacts with various nucleophiles, especially amines and thiols. Reacts with aqueous potassium hydroxide to form a highly reactive compound. The crude product from aqueous nitrosation is pyrophoric but recrystallized material is stable .

Health Hazard

Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Poison by ingestion, intraperitoneal, and intravenous routes. Moderately toxic by subcutaneous route. Experimental reproductive effects. Human mutation data reported. An explosive sensitive to heat or impact. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits very toxic fumes of NOx.

Carcinogenicity

N-Methyl-N-nitro-N-nitrosoguanidine (MNNG) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Synthetic route

N-methyl-N'-nitroguanidine (4245-76-5) → N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7)

Conditions	Yield
With nitric acid; sodium nitrite at 10℃;

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (2E,4E)-5-Bromo-2,4-dimethyl-penta-2,4-dienoic acid (400736-91-6) → (2E,4E)-5-bromo-2,4-dimethyl-penta-2,4-dienoic acid methyl ester (400736-94-9)

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; for 0.25h; Stage #2: (2E,4E)-5-Bromo-2,4-dimethyl-penta-2,4-dienoic acid In diethyl ether	99%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + C17H21FO3 (1009365-40-5) → methyl 2-(9-(4-fluorophenyl)-3-hydroxybicyclo[3.3.1]nonan-9-yl)acetate (1009367-58-1)

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.0833333h; Stage #2: C17H21FO3 In diethyl ether; dichloromethane at 0℃; for 0.166667h;	99%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + 5-benzoylaminopentanoic acid (15647-47-9) → methyl N-benzoyl-5-aminopentanoate (17079-25-3)

Conditions	Yield
With sodium hydroxide In methanol; diethyl ether at 0℃;	99%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + trans-methyl 4-(4-bromophenyl)but-2-enoate (1310810-17-3) → trans-methyl 2-(4-bromobenzyl)cyclopropanecarboxylate

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; for 0.25h; Stage #2: trans-methyl 4-(4-bromophenyl)but-2-enoate With palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h;	98%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (4aR,6S,8S,8aR)-6-(3-azidopropoxy)-2,2-di-tert-butyl-8-(((4aR,6R,7S,8S,8aR)-2,2-di-tert-butyl-7,8-bis((tert-butyldimethylsilyl)oxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)oxy)tetrahydropyrano[3,2-d][1,3,2]dioxasilin-7(6H)-one → (2S,4a’R,6’S,8’S,8a’R)-6’-(3-azidopropoxy)-2’,2’-di-tert-butyl-8’-(((4aR,6R,7S,8S,8aR)-2,2-di-tert-butyl-7,8-bis((tert-butyldimethylsilyl)oxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)oxy)tetrahydro-6’H-spiro[oxirane-2,7’-pyrano[3,2-d][1,3,2]dioxasiline]

Conditions	Yield
With potassium hydroxide In diethyl ether; ethanol; water for 0.166667h; Inert atmosphere;	98%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + Mrz 2/138 (110916-46-6) → N-[2-(3,5-dimethyl-1-adamantyl)ethyl]-nitroguanidine

Conditions	Yield
In diethyl ether; water at 22℃; for 1.5h;	96.5%
In diethyl ether; water at 20 - 22℃; for 0.5h;	96.5%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (E)-methyl 4-(4-((3-phenoxybenzyl)oxy)bicyclo[2.2.1]heptan-1-yl)but-2-enoate → methyl 2-((4-((3-phenoxybenzyl)oxy)bicyclo[2.2.1]heptan-1-yl)methyl)cyclopropanecarboxylate

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With palladium diacetate; potassium hydroxide In diethyl ether; water at 0℃; for 0.333333h; Stage #2: (E)-methyl 4-(4-((3-phenoxybenzyl)oxy)bicyclo[2.2.1]heptan-1-yl)but-2-enoate With palladium diacetate In tetrahydrofuran at 0 - 20℃; for 1h;	95%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (2E)-N-benzylbut-2-enamide (89232-30-4) → N-benzyl-2-methylcyclopropanecarboxamide

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With water; potassium hydroxide In diethyl ether at 0℃; for 0.25h; Stage #2: (2E)-N-benzylbut-2-enamide With palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h;	94%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + N-benzoyl-N-((E)-2-butenyl)-5-aminopentanoic acid → methyl N-benzoyl-N-((E)-2-butenyl)-5-aminopentanoate

Conditions	Yield
With sodium hydroxide In diethyl ether at 0℃;	94%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + 3-amino-1H-1,2,4-triazole-5-carbohydrazide (3641-15-4) → N-(5'-amino-1H,1'H-[3,3'-bi(1,2,4-triazol)]-5-yl)nitramide

Conditions	Yield
In methanol; water at 80℃; for 2h;	93%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (E)-methyl-cis-3-(3-(4-bromophenyl)cyclobutyl)acrylate → methyl trans-2-(cis-3-(4-bromophenyl)cyclobutyl)cyclopropanecarboxylate

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With water; potassium hydroxide In diethyl ether at 0℃; for 0.333333h; Stage #2: (E)-methyl-cis-3-(3-(4-bromophenyl)cyclobutyl)acrylate With palladium diacetate In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h;	92%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (E)-5-(4-bromophenyl)pent-2-enoic acid ethyl ester → trans-ethyl 2-(4-bromophenethyl)cyclopropanecarboxylate

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at -78 - 0℃; for 0.5h; Stage #2: (E)-5-(4-bromophenyl)pent-2-enoic acid ethyl ester With palladium diacetate In diethyl ether; water at 0 - 20℃; Stage #3: With acetic acid In diethyl ether at 20℃; for 0.5h;	91%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (4-amino-furazan-3-yl)-acetic acid hydrazide → C5H6N8O3

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine; (4-amino-furazan-3-yl)-acetic acid hydrazide In methanol; water for 2h; Heating; Stage #2: With potassium hydroxide In water for 2h; Stage #3: With nitric acid In water at 50℃; pH=3;	90%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + silver nitrate → silver (I) nitro cyanamide (20236-50-4)

Conditions	Yield
In sodium hydroxide solvation of 16 g NaOH in 600 ml H2O and addition of 44.1 g of the guanidine under stirring at 0°C within 10 minutes, shaking for another 20 minutes and addition of 36 ml concentrated HNO3 in 150 ml H2O and 51 g AgNO3 in 150 ml H2O;; precipitation; washing with hot H2O;;	89.4%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + 3-methyl-4-(1-methyl-7-oxo-3-(pyridin-2-yl)-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-4-yl)benzoic acid (1616364-26-1) → methyl 3-methyl-4-(1-methyl-7-oxo-3-(pyridin-2-yl)-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-4-yl)benzoate (1616364-27-2)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; diethyl ether; water at 0℃; Inert atmosphere;	88%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (E)-methyl 5-(4-bromophenyl)pent-2-enoate → trans-methyl 2-(4-bromophenethyl)cyclopropanecarboxylate

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.25h; Stage #2: (E)-methyl 5-(4-bromophenyl)pent-2-enoate With palladium diacetate In tetrahydrofuran; diethyl ether; water at 20℃; for 1h;	88%

tert-butyl (3R,5R,6S)-3-(2-methylprop-2-enyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate (681128-21-2) + N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) → tert-butyl (3R,5R,6S)-3-[(1-methylcyclopropyl)methyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate (681128-22-3)

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.0833333h; Stage #2: tert-butyl (3R,5R,6S)-3-(2-methylprop-2-enyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate; palladium diacetate In tetrahydrofuran; diethyl ether at 0℃;	86%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + 3-Aminofurazan-4-carboxylic acid hydrazide → 2-(4-aminofurazan-3-carbonyl)-N'-nitrohydrazine-1-carboximidamide

Conditions	Yield
With water In methanol for 2h; Heating;	86%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + furoxancarboxylic acid hydrazide (37895-46-8) → C5H5N7O4

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine; furoxancarboxylic acid hydrazide In methanol; water for 2h; Heating; Stage #2: With potassium hydroxide In methanol; water for 2h; Stage #3: With nitric acid at 50℃; pH=3;	85%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (2E)-N-benzylbut-2-enamide (89232-30-4) → N-benzyl-2-methylcyclopropane-1-carboxamide

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 20℃; for 0.166667h; Stage #2: (2E)-N-benzylbut-2-enamide; palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h;	83%
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at -78 - 20℃; for 0.0833333h; Stage #2: (2E)-N-benzylbut-2-enamide; palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h;

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + ethyl (E)-3-(3-fluoro-4-methoxyphenyl)acrylate (187872-44-2) → 2-(3-fluoro-4-methoxyphenyl)cyclopropanecarboxylic acid ethyl ester (1234845-29-4)

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With water; potassium hydroxide In diethyl ether at 0℃; for 0.0333333h; Stage #2: ethyl (E)-3-(3-fluoro-4-methoxyphenyl)acrylate; palladium diacetate In diethyl ether at 0 - 5℃; for 4h; Stage #3: With acetic acid In diethyl ether	83%
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; Stage #2: ethyl (E)-3-(3-fluoro-4-methoxyphenyl)acrylate; palladium diacetate In diethyl ether; water at 0 - 5℃; Stage #3: With acetic acid In diethyl ether; water	83%

diazomethane (186581-53-3, 908094-01-9) + N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + 3-(2-isopropylphenyl)propanoyl chloride (365554-36-5) → 1-diazo-4-(2-isopropylphenyl)butan-2-one (365554-38-7)

Conditions	Yield
In dichloromethane	82%

N-[5-(N-4-toluenesulfonyl-amino)pyrimidin-4-yl]-L-4-(N,N-dimethylcarbarnyloxy)phenylalanine tert-butyl ester (285139-32-4) + N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) → N-[5-(N-methyl-N-4-toluenesulfonylamino)pyrimidin-4-yl]-L-4-(N,N-dimethylcarbarnyloxy)phenylalanine tert-butyl ester (285139-33-5)

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With sodium hydroxide In diethyl ether at 0℃; for 0.416667h; Stage #2: Stage #3: N-[5-(N-4-toluenesulfonyl-amino)pyrimidin-4-yl]-L-4-(N,N-dimethylcarbarnyloxy)phenylalanine tert-butyl ester In diethyl ether; dichloromethane at 0℃; for 0.25h;	82%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + 3-Aminofurazan-4-carboxylic acid hydrazide → 3-amino-4-(5-nitramino-1,2,4-triazol-3-yl)furazan monohydrate

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine; 3-Aminofurazan-4-carboxylic acid hydrazide In methanol; water for 2h; Heating; Stage #2: With potassium hydroxide In water for 2h; Stage #3: With nitric acid In water at 50℃; pH=3;	82%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (R)-3-phenylbutanehydrazide → (R)-N-(5-(2-phenylpropyl)-1H-1,2,4-triazol-3-yl)nitramide

Conditions	Yield
With nitric acid; potassium hydroxide In water Reflux;	82%

C29H38BrN3O5 + N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) → methyl 4-[[(3S)-3-(4-bromophenylureido)-3-(tert-butoxycarbonyl)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butyrate

Conditions	Yield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.166667h; Stage #2: C29H38BrN3O5 In diethyl ether; dichloromethane; water at 0℃; for 0.5h;	81%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (2S,3R)-4-benzyl 1-tert-butyl 2-allyl-3-(3,3,3-trifluoropropyl)succinate (1581734-68-0) → (2R,3S)-1-benzyl 4-tert-butyl 3-(cyclopropylmethyl)-2-(3,3,3-5 trifluoropropyl)succinate (1581734-69-1)

Conditions	Yield
With palladium diacetate; potassium hydroxide In diethyl ether; water at 0℃; for 3h;	81%
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; Stage #2: (2S,3R)-4-benzyl 1-tert-butyl 2-allyl-3-(3,3,3-trifluoropropyl)succinate With palladium diacetate In diethyl ether; water at 0℃; for 3h;	81%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) → diazomethane (186581-53-3, 908094-01-9)

Conditions	Yield
With potassium hydroxide at -20.1℃;	80%
With potassium hydroxide
With potassium hydroxide In diethyl ether; water for 0.25h;

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (4-amino-furazan-3-yl)-acetic acid hydrazide → C5H8N8O4

Conditions	Yield
In methanol; water for 2h; Heating;	80%

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + (4aR,6S,8S,8aR)-6-(3-azidopropoxy)-2,2-di-tert-butyl-8-(((4aR,6R,7R,8S,8aR)-2,2-di-tert-butyl-7,8-bis((tert-butyldimethylsilyl)oxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)oxy)tetrahydropyrano[3,2-d][1,3,2]dioxasilin-7(6H)-one → (2S,4a’R,6’S,8’S,8a’R)-6’-(3-azidopropoxy)-2’,2’-di-tert-butyl-8’-(((4aR,6R,7R,8S,8aR)-2,2-di-tert-butyl-7,8-bis((tert-butyldimethylsilyl)oxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)oxy)tetrahydro-6’H-spiro[oxirane-2,7’-pyrano[3,2-d][1,3,2]dioxasiline]

Conditions	Yield
With potassium hydroxide In diethyl ether; ethanol; water for 0.166667h; Inert atmosphere;	78%

Upstream product

• 4245-76-5 N-methyl-N'-nitroguanidine 
• 4245-76-5 N-Methyl-N'-nitroguanidine 

Downstream Products

• 53913-64-7 piperidine-1-carbonimidic acid nitroamide 
• 855926-49-7 N-(2-acetylamino-ethyl)-N'-nitro-guanidine 
• 93071-35-3 N-(3-amino-4-methyl-phenyl)-N'-nitro-guanidine 
• 6937-92-4 N-(2-chloro-ethyl)-N'-nitro-guanidine 
• 14955-36-3 1-[2]naphthylazo-[2]naphthylamine 
• 18588-16-4 5-nitroaminotetrazole 
• 35089-66-8 1-(t-Butyl)-3-nitroguanidin 
• 52662-73-4 N-(3-methoxy-phenyl)-N'-nitro-guanidine 
• 6272-68-0 N-cyclohexyl-N'-nitro-guanidine 
• 6318-13-4 N-(4-methoxy-phenyl)-N'-nitro-guanidine 
• 42216-32-0 N-(N''-nitrocarbamimidoylamino)benzamide 
• 6317-95-9 3-Nitro-1-<2-hydroxy-ethyl>-guanidin 
• 6266-34-8 2-(2-nitroamino-4,5-dihydro-imidazol-1-yl)-ethanol 
• 6266-33-7 N-nitro-N'-phenethyl-guanidine 

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