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Preferred IUPAC name 4-Amino-2-methylnaphthalen-1-ol | |
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Properties | |
C11H11NO | |
Molar mass | 173.215 g·mol−1 |
Appearance | HCl: white crystalline powder [1] |
Solubility | HCl: soluble in water, poorly soluble in ethanol, insoluble in diethyl ether [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
4-Amino-2-methyl-1-naphthol is a menadione analog. Its hydrochloride (HCl) salt is often called vitamin K5. The HCl salt has been used as a medicine for vitamin K deficiency under tradenames such as Synkamin, [1] [2] which was sold by Parke-Davis, but has since been discontinued. [3]
Vitamin K function of the compound was first noted in 1940. [4] [5]
Oral lethal dose for the HCl salt in rats is 0.7 g/kg. [5]
4-Amino-2-methyl-1-naphthol HCl salt is a vitamin K and prevents bleeding caused by vitamin K deficiency when given via intravenous or intramuscular injections at doses of about 1–3 mg. HCl salt is water-soluble and its parenteral administration requires no emulsifiers [6] [7] unlike fat-soluble phylloquinone for example, which is often in formulations with lecithin or glycocholic acid. [8] Parenterally given 1 mg/ml aqueous solutions and orally taken 4 mg tablets of the HCl salt have been available commercially. [1]
4-Amino-2-methyl-1-naphthol HCl salt has a mass of 209.57 g/mol. [1] It darkens at 262 °C and decays without melting at 280–282 °C. [2]
HCl salt breaks down in aqueous solutions via oxidation which is quite fast at neutral pH. First a pink and later a purple precipitant forms. The colored precipitant is (4-oxy-2-methylnaphtylimine)-2-methyl-1,4-naphthoquinone, which is a condensation reaction product of 4-amino-2-methyl-1-naphthol and menadione. Latter is formed via oxidation and deamination of 4-amino-2-methyl-1-naphthol. [9]
4-Amino-2-methyl-1-naphthol can be made from 2-methylnaphthalene or menadione. [2]
4-Amino-2-methyl-1-naphthol HCl salt prevents the growth of different molds and bacteria. Thus it has been studied as potential food preservative. [10] [9]
HCl salt has been studied as a potential treatment for cancer as it prevents glycolysis in cancer cells, which provides them energy for growth. [11]
Thiamine, also known as thiamin and vitamin B1, is a vitamin, an essential micronutrient, that cannot be made in the body. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thiamine are required for some metabolic reactions, including the breakdown of glucose and amino acids.
Vitamin K refers to structurally similar, fat-soluble vitamers found in foods and marketed as dietary supplements. The human body requires vitamin K for post-synthesis modification of certain proteins that are required for blood coagulation or for controlling binding of calcium in bones and other tissues. The complete synthesis involves final modification of these so-called "Gla proteins" by the enzyme gamma-glutamyl carboxylase that uses vitamin K as a cofactor.
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Methyllycaconitine (MLA) is a diterpenoid alkaloid found in many species of Delphinium (larkspurs). In common with many other diterpenoid alkaloids, it is toxic to animals, although the acute toxicity varies with species. Early research was focused on identifying, and characterizing the properties of methyllycaconitine as one of the principal toxins in larkspurs responsible for livestock poisoning in the mountain rangelands of North America. Methyllycaconitine has been explored as a possible therapeutic agent for the treatment of spastic paralyses in man, and it has been shown to have insecticidal properties. Most recently, it has become an important molecular probe for studying the pharmacology of the nicotinic acetylcholine receptor.
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Menatetrenone (INN), also known as MK-4, is one of the nine forms of vitamin K2.
Dimethylglycine (DMG) is a derivative of the amino acid glycine with the structural formula (CH3)2NCH2COOH. It can be found in beans and liver, and has a sweet taste. It can be formed from trimethylglycine upon the loss of one of its methyl groups. It is also a byproduct of the metabolism of choline.
Remacemide is a drug which acts as a low-affinity NMDA antagonist with sodium channel blocking properties. It has been studied for the treatment of acute ischemic stroke, epilepsy, Huntington's disease, and Parkinson's disease.
N-Methyltyramine (NMT), also known as 4-hydroxy-N-methylphenethylamine, is a human trace amine and natural phenethylamine alkaloid found in a variety of plants. As the name implies, it is the N-methyl analog of tyramine, which is a well-known biogenic trace amine with which NMT shares many pharmacological properties. Biosynthetically, NMT is produced by the N-methylation of tyramine via the action of the enzyme phenylethanolamine N-methyltransferase in humans and tyramine N-methyltransferase in plants.
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