MINOCYCLINE
minocycline Hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 0 - 5℃; for 1h; pH=1 - 2; Solvent; | 92.7% |
Conditions | Yield |
---|---|
Stage #1: O-benzoyl N,N-dimethylhydroxylamine; C24H26N2O9 With iron(III) chloride In toluene at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 0.5h; | 90% |
dimethyl sulfate
7-amino-6-desmethyl-6-deoxytetracycline
minocycline Hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; 5%-palladium/activated carbon In 2-methoxy-ethanol; water under 5250.53 - 6750.68 Torr; for 3h; | 81.6% |
Conditions | Yield |
---|---|
Stage #1: O-benzoyl N,N-dimethylhydroxylamine; C28H26N2O8 With iron(III) chloride In toluene at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 0.5h; | 81% |
formaldehyd
7-amino-6-desmethyl-6-deoxytetracycline
minocycline Hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; formic acid; 5%-palladium/activated carbon In 2-methoxy-ethanol; water under 5250.53 - 6750.68 Torr; for 3h; Reagent/catalyst; | 77.8% |
minocycline Hydrochloride
Conditions | Yield |
---|---|
Stage #1: C34H49N3O9Si With hydrogen fluoride In water; acetonitrile at 23 - 40℃; Stage #2: With hydrogenchloride In water HPLC; | 24.6 mg |
sancycline
minocycline Hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 5 °C 2.1: iron(III) chloride / toluene / 2 h / 20 °C / Inert atmosphere 2.2: 0.5 h View Scheme |
minocycline Hydrochloride
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 0℃; for 1.5h; | 93% |
Stage #1: minocycline Hydrochloride With sulfuric acid at 0 - 10℃; under 50 - 300 Torr; for 4.75 - 93.75h; nitrogen flow; Stage #2: With nitric acid In water at 0 - 10℃; for 1.66667 - 2.16667h; Product distribution / selectivity; | 93% |
With nitric acid; potassium nitrate In cyclohexane; sulfuric acid | 90% |
minocycline Hydrochloride
(4S,4aS,5aR,12S)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxanaphthacene-2-carboxamide
Conditions | Yield |
---|---|
Stage #1: minocycline Hydrochloride With sulfuric acid at 5℃; under 50 - 760.051 Torr; for 3h; Stage #2: With nitric acid In water at 6℃; for 1.66667h; Product distribution / selectivity; | 93% |
With sulfuric acid; potassium nitrate at 0℃; for 1.5h; | 76.6% |
With sulfuric acid; potassium nitrate at 0 - 5℃; for 2h; Product distribution / selectivity; | |
With sulfuric acid; nitric acid In water for 0.5 - 6h; Product distribution / selectivity; | |
With hydrogenchloride; sulfuric acid; nitric acid In water for 1.66667h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 24 - 40℃; for 24h; Tscherniac-Einhorn reaction; | 76% |
1-Iodooctane
minocycline Hydrochloride
10-O-octyl-7-dimethylamino-6-demethyl-6-deoxytetracycline
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1h; | 65% |
Iododecane
minocycline Hydrochloride
10-O-decyl-7-dimethylamino-6-demethyl-6-deoxytetracycline
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 2h; | 65% |
minocycline Hydrochloride
1-Iodohexane
10-O-hexyl-7-dimethylamino-6-demethyl-6-deoxytetracycline
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1h; | 64% |
1-iodotetradecane
minocycline Hydrochloride
10-O-tetradecyl-7-dimethylamino-6-demethyl-6-deoxytetracycline
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 3h; | 57% |
minocycline Hydrochloride
MINOCYCLINE
Conditions | Yield |
---|---|
With acetic acid In methanol at 42℃; for 3h; Temperature; Reagent/catalyst; Solvent; | 55.4% |
With sodium hydrogencarbonate In water pH=6.5 - 7.0; |
C10H19NO3
minocycline Hydrochloride
A
C32H44N4O9
B
C39H57N5O9
Conditions | Yield |
---|---|
Stage #1: C10H19NO3; minocycline Hydrochloride With trifluorormethanesulfonic acid at 22℃; for 72h; Tscherniac-Einhorn reaction; Stage #2: C10H19NO3 With trifluorormethanesulfonic acid at 35 - 40℃; for 24h; Tscherniac-Einhorn reaction; | A 53% B 39% |
C10H19NO3
minocycline Hydrochloride
A
C24H29N3O8
B
C31H42N4O8
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 22℃; for 72h; Tscherniac-Einhorn reaction; | A 33% B 50% |
1-Iodododecane
minocycline Hydrochloride
10-O-dodecyl-7-dimethylamino-6-demethyl-6-deoxytetracycline
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 3h; | 46% |
minocycline Hydrochloride
(4S,4aS,5aR,12aS)-4-Dimethylamino-3,7,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide; hydrochloride
Conditions | Yield |
---|---|
With ascorbic acid; potassium hexacyanoferrate(III) 1) 2) H2O; |
minocycline Hydrochloride
Conditions | Yield |
---|---|
With hydrazine hydrate In water at 20℃; for 16h; |
minocycline Hydrochloride
[((5aR,6aS,7S,10aS)-9-Carbamoyl-4,7-bis-dimethylamino-1,8,10a,11-tetrahydroxy-10,12-dioxo-5,5a,6,6a,7,10,10a,12-octahydro-naphthacen-2-ylcarbamoyl)-methyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 93 percent / KNO3, H2SO4 / 1.5 h / 0 °C 2: 96 percent / H2, 2 N aq. H2SO4 / 10percent Pd/C / 2-methoxy-ethanol / 1.5 h / 2068.6 Torr 3: 65 mg / AcONa / tetrahydrofuran; H2O / 2 h View Scheme |
minocycline Hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 93 percent / KNO3, H2SO4 / 1.5 h / 0 °C 2: 96 percent / H2, 2 N aq. H2SO4 / 10percent Pd/C / 2-methoxy-ethanol / 1.5 h / 2068.6 Torr View Scheme | |
Stage #1: minocycline Hydrochloride With sulfuric acid; potassium nitrate at -5 - -1℃; Stage #2: With hydrogen; palladium 10% on activated carbon at 20 - 25℃; under 2585.81 Torr; |
minocycline Hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 93 percent / KNO3, H2SO4 / 1.5 h / 0 °C 2: 96 percent / H2, 2 N aq. H2SO4 / 10percent Pd/C / 2-methoxy-ethanol / 1.5 h / 2068.6 Torr 3: 65 mg / AcONa / tetrahydrofuran; H2O / 2 h 4: 65 mg / 5 h / Ambient temperature View Scheme |
minocycline Hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 93 percent / KNO3, H2SO4 / 1.5 h / 0 °C 2: 96 percent / H2, 2 N aq. H2SO4 / 10percent Pd/C / 2-methoxy-ethanol / 1.5 h / 2068.6 Torr 3: Na2CO3, N,N-dimethylpropyleneurea / acetonitrile / 0.5 h / Ambient temperature View Scheme |
minocycline Hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 93 percent / KNO3, H2SO4 / 1.5 h / 0 °C 2: 96 percent / H2, 2 N aq. H2SO4 / 10percent Pd/C / 2-methoxy-ethanol / 1.5 h / 2068.6 Torr 3: Na2CO3, N,N-dimethylpropyleneurea / acetonitrile / 0.5 h / Ambient temperature View Scheme |
minocycline Hydrochloride
Conditions | Yield |
---|---|
Stage #1: minocycline Hydrochloride With hydrazine In water at 20℃; Stage #2: With trifluoroacetic acid In water; acetonitrile Stage #3: With triethylamine In water |
minocycline Hydrochloride
Conditions | Yield |
---|---|
With ammonia In ethanol at 20℃; for 4h; Heating / reflux; |
C10H13F6NO3
minocycline Hydrochloride
A
C24H29N3O8
B
C32H41F3N4O9
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 22℃; Tscherniac-Einhorn reaction; | A 50 %Chromat. B 30 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: C10H13F6NO3; minocycline Hydrochloride With trifluorormethanesulfonic acid at 22℃; Tscherniac-Einhorn reaction; Stage #2: In trifluorormethanesulfonic acid at 22℃; for 18h; |
C10H13Cl6NO3
minocycline Hydrochloride
A
C26H31N3O9
B
C26H33N3O10
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid Tscherniac-Einhorn reaction; |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 22℃; for 0.5h; Tscherniac-Einhorn reaction; |
1. Introduction of Minocycline hydrochloride
Minocycline hydrochloride is one kind of crystalline yellow powder. The IUPAC Name of this chemical is (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide hydrochloride. Besides, the Product Category of Minocycline hydrochloride is Antibacterial;Antibiotic Explorer;Intermediates & Fine Chemicals;Pharmaceuticals;Peptide Synthesis/Antibiotics. In addition, Minocycline hydrochloride Classification Code is Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Drug / Therapeutic Agent; Human Data; Natural Product. Minocycline hydrochloride can soluble in water.
2. Properties of Minocycline hydrochloride
Physical properties about Minocycline hydrochloride are:
(1)H-Bond Donor: 6; (2)H-Bond Acceptor: 9; (3)Molecular Formula: C23H27N3O7.ClH; (4)Molecular Weight: 493.94; (5)EINECS: 237-099-7; (6)Flash Point: 445.4 °C; (7)Enthalpy of Vaporization: 123.88 kJ/mol; (8)Boiling Point: 812.8 °C at 760 mmHg; (9)Vapour Pressure: 6.33E-28 mmHg at 25 °C; (10)Melting point: 205-210 °C (dec); (11)Storage tempreture: 2-8 °C; (12)Appearance: Yellow crystalline powder.
3. Structure Descriptors of Minocycline hydrochloride
(1)InChI: InChI=1S/C23H27N3O7.ClH/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28;/h5-6,9,11,17,27-28,31,33H,7-8H2,1-4H3,(H2,24,32);1H/t9-,11-,17-,23-;/m0./s1
(2)InChIKey: WTJXVDPDEQKTCV-VQAITOIOSA-N
(3)Canonical SMILES: CN(C)C1C2CC3CC4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C.Cl
(4)Isomeric SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C.Cl
(5)Smiles: Cl.[C@@H]12[C@](C(=C3[C@H](C2)Cc2c(C3=O)c(ccc2N(C)C)O)O)(C(=O)C(=C([C@H]1N(C)C)O)C(=O)N)O
4. Toxicity of Minocycline hydrochloride
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | oral | 14286ug/kg/10 (14.286mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION LUNGS, THORAX, OR RESPIRATION: DYSPNEA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Archives of Internal Medicine. Vol. 154, Pg. 1633, 1994. |
man | TDLo | intravenous | 2857ug/kg (2.857mg/kg) | LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Internal Medicine. Vol. 33, Pg. 177, 1994. |
man | TDLo | oral | 11429ug/kg/4D (11.429mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Archives of Dermatology. Vol. 123, Pg. 18, 1987. |
man | TDLo | oral | 3893mg/kg/4Y- (3893mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Archives of Dermatology. Vol. 122, Pg. 17, 1986. |
mouse | LD50 | intraperitoneal | 299mg/kg (299mg/kg) | Drugs in Japan Vol. 6, Pg. 811, 1982. | |
mouse | LD50 | intravenous | 154mg/kg (154mg/kg) | Drugs in Japan Vol. 6, Pg. 811, 1982. | |
mouse | LD50 | oral | 3600mg/kg (3600mg/kg) | Drugs in Japan Vol. 6, Pg. 811, 1982. | |
mouse | LD50 | subcutaneous | 2290mg/kg (2290mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 21, Pg. 319, 1990. | |
mouse | LDLo | parenteral | 620mg/kg (620mg/kg) | Chemotherapy Vol. 24, Pg. 17, 1978. | |
rat | LD50 | intraperitoneal | 331mg/kg (331mg/kg) | Drugs in Japan Vol. 6, Pg. 811, 1982. | |
rat | LD50 | intravenous | 164mg/kg (164mg/kg) | Drugs in Japan Vol. 6, Pg. 811, 1982. | |
rat | LD50 | oral | 2380mg/kg (2380mg/kg) | Drugs in Japan Vol. 6, Pg. 811, 1982. | |
rat | LD50 | subcutaneous | 1700mg/kg (1700mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 21, Pg. 319, 1990. | |
women | TDLo | oral | 42mg/kg/3W-I (42mg/kg) | BLOOD: AGRANULOCYTOSIS BLOOD: OTHER CHANGES MUSCULOSKELETAL: JOINTS | Archives of Internal Medicine. Vol. 154, Pg. 1983, 1994. |
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