Title: Quatrimycin
CAS Registry Number: 79-85-6
CAS Name: [4R-(4a,4ab,5ab,6a,12ab)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
Additional Names: epitetracycline
Molecular Formula: C22H24N2O8
Molecular Weight: 444.43
Percent Composition: C 59.45%, H 5.44%, N 6.30%, O 28.80%
Literature References: Prepn by epimerization of tetracycline: McCormick et al., J. Am. Chem. Soc. 79, 2849 (1957); Kaplan et al., Antibiot. Chemother. 7, 569 (1957); Remmers et al., J. Pharm. Sci. 52, 752 (1963). Acute toxicity: L. Kung, H. Sun, Yao Hsueh Hsueh Pao 13, 244 (1966), C.A. 65, 7869e (1966).
Derivative Type: Monohydrate
Properties: Crystals, mp 178° dec. [a]D25 -335° (c = 0.5 in 0.03N HCl). uv max (0.01N H2SO4): 216, 255, 270, 355 (e 13,900, 16,400, 15,200, 14,700). LD50 i.v. in mice: 85.8 mg/kg (Kung, Sun).
Melting point: mp 178° dec
Optical Rotation: [a]D25 -335° (c = 0.5 in 0.03N HCl)
Absorption maximum: uv max (0.01N H2SO4): 216, 255, 270, 355 (e 13,900, 16,400, 15,200, 14,700)
Toxicity data: LD50 i.v. in mice: 85.8 mg/kg (Kung, Sun)
Derivative Type: Ammonium salt monohydrate
Molecular Formula: C22H27N3O8.H2O
Molecular Weight: 479.48
Percent Composition: C 55.11%, H 6.10%, N 8.76%, O 30.03%
Properties: Yellow crystals, mp 170° dec. [a]D25 -321° (c = 0.5 in 0.03N HCl). Soly in water >50 mg/kg.
Melting point: mp 170° dec
Optical Rotation: [a]D25 -321° (c = 0.5 in 0.03N HCl)
Derivative Type: Hydrochloride
Molecular Formula: C22H25ClN2O8
Molecular Weight: 480.90
Percent Composition: C 54.95%, H 5.24%, Cl 7.37%, N 5.83%, O 26.62%
Properties: Amorphous yellow solid. [a]D25 -325° (c = 0.58 in 0.2N HCl). Soly in water >100 mg/ml.
Optical Rotation: [a]D25 -325° (c = 0.58 in 0.2N HCl)
Derivative Type: Methiodide
Molecular Formula: C23H27IN2O8
Molecular Weight: 586.37
Percent Composition: C 47.11%, H 4.64%, I 21.64%, N 4.78%, O 21.83%
Properties: Crystals, mp 161-162°. [a]D25 -265° (c = 0.5 in 0.03N HCl).
Melting point: mp 161-162°
Optical Rotation: [a]D25 -265° (c = 0.5 in 0.03N HCl)
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