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Substance Name: Menadione [USP:BAN]
RN: 58-27-5
UNII: 723JX6CXY5
InChIKey: MJVAVZPDRWSRRC-UHFFFAOYSA-N

Note

  • A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.

Molecular Formula

  • C11-H8-O2

Molecular Weight

  • 172.182
 

Classification Codes

  • Antifibrinolytic Agents
  • Coagulants
  • Drug / Therapeutic Agent
  • Fibrin Modulating Agents
  • Growth Substances
  • Hematologic Agents
  • Hemostatics
  • Micronutrients
  • Mutation Data
  • Reproductive Effect
  • Tumor Data
  • Vitamin (Prothrombogenic)
  • Vitamins

Names and Synonyms

Name of Substance

  • 1,4-Naphthalenedione, 2-methyl-
  • Menadione
  • Menadione [USP:BAN]
  • Vitamin K3

MeSH Heading

  • Vitamin K 3

Synonyms

  • 1,4-Naphthalenedione, 2-methyl-
  • 1,4-Naphthoquinone, 2-methyl-
  • 2-Methyl-1,4-naftochinon
  • 2-Methyl-1,4-naftochinon [Czech]
  • 2-Methyl-1,4-naphthalenedione
  • 2-Methyl-1,4-naphthochinon
  • 2-Methyl-1,4-naphthochinon [German]
  • 2-Methyl-1,4-naphthoquinone
  • 2-Methylnaphthoquinone
  • 3-Methyl-1,4-naphthoquinone
  • AI3-14700
  • Aquakay
  • Aquinone
  • CCRIS 6672
  • EINECS 200-372-6
  • Hemodal
  • HSDB 3354
  • Juva-K
  • K-Thrombyl
  • K-Vitan
  • Kaergona
  • Kanone
  • Kappaxan
  • Kappaxan (VAN)
  • Kappaxin
  • Karcon
  • Kareon
  • Kativ-G
  • Kayklot
  • Kaykot
  • Kayquinone
  • Kipca
  • Kipca-oil soluble
  • Klottone
  • Koaxin
  • Kolklot
  • Memodol
  • Menadion
  • Menadione
  • Menadionum
  • Menaphthon
  • Menaphthone
  • Menaquinone
  • Menaquinone 0
  • Mitenon
  • Mitenone
  • MNQ
  • NSC 4170
  • Panosine
  • Prokayvit
  • Synkay
  • Thyloquinone
  • UNII-723JX6CXY5
  • USAF EK-5185
  • Vitamin K0
  • Vitamin K2(0)
  • Vitamin K3

Systematic Names

  • 1,4-Naphthalenedione, 2-methyl-
  • 1,4-Naphthoquinone, 2-methyl-
  • Menadione

Superlist Name

  • Menadione

Registry Numbers

CAS Registry Number

  • 58-27-5

FDA UNII

  • 723JX6CXY5

System Generated Number

  • 0000058275

Structure Descriptors

InChI

InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

InChIKey

MJVAVZPDRWSRRC-UHFFFAOYSA-N

Smiles

CC1=CC(=O)c2ccccc2C1=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo intraperitoneal 100mg/kg (100mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 500mg/kg (500mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.
mouse LD50 subcutaneous 138mg/kg (138mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.
rabbit LDLo oral 230mg/kg (230mg/kg) VASCULAR: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.
rat LD50 intraperitoneal 75mg/kg (75mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 107 deg C   EXP
log P (octanol-water) 2.2 (none)   EXP
Water Solubility 160 mg/L 30 EXP
Vapor Pressure 1.88E-04 mm Hg 25 EST
Henry's Law Constant 3.09E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.15E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.