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Minocycline hydrochloride

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Name

Minocycline hydrochloride

EINECS 237-099-7
CAS No. 13614-98-7 Density N/A
PSA 164.63000 LogP 1.68890
Solubility Freely soluble in water Melting Point 205-210 °C(dec)
Formula C23H27N3O7.ClH Boiling Point 812.8 °C at 760 mmHg
Molecular Weight 493.944 Flash Point 445.4 °C
Transport Information N/A Appearance crystalline yellow powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 13614-98-7 (Minocycline hydrochloride) Hazard Symbols IrritantXi
Synonyms

2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,monohydrochloride (8CI);2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,monohydrochloride, (4S,4aS,5aR,12aS)- (9CI);2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,monohydrochloride, [4S-(4a,4aa,5aa,12aa)]-;Acnez;Klinomycin;Minocin;Minocyclinehydrochloride;Minomycin;NSC 141993;Periocline;Vectrin;Minocycline HCL;2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,hydrochloride (1:1), (4S,4aS,5aR,12aS)-;

Article Data 6

Minocycline hydrochloride Synthetic route

10118-90-8

MINOCYCLINE

13614-98-7

minocycline Hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 5℃; for 1h; pH=1 - 2; Solvent;92.7%
58105-38-7

O-benzoyl N,N-dimethylhydroxylamine

C24H26N2O9

13614-98-7

minocycline Hydrochloride

Conditions
ConditionsYield
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%
77-78-1

dimethyl sulfate

5679-00-5

7-amino-6-desmethyl-6-deoxytetracycline

13614-98-7

minocycline Hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; 5%-palladium/activated carbon In 2-methoxy-ethanol; water under 5250.53 - 6750.68 Torr; for 3h;81.6%
58105-38-7

O-benzoyl N,N-dimethylhydroxylamine

C28H26N2O8

13614-98-7

minocycline Hydrochloride

Conditions
ConditionsYield
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%
50-00-0

formaldehyd

5679-00-5

7-amino-6-desmethyl-6-deoxytetracycline

13614-98-7

minocycline Hydrochloride

Conditions
ConditionsYield
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%

C34H49N3O9Si

13614-98-7

minocycline Hydrochloride

Conditions
ConditionsYield
Stage #1: C34H49N3O9Si With hydrogen fluoride In water; acetonitrile at 23 - 40℃;
Stage #2: With hydrogenchloride In water HPLC;
24.6 mg
Conditions
ConditionsYield
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
13614-98-7

minocycline Hydrochloride

<4S-(4α,12aα)>-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxamide disulfate

Conditions
ConditionsYield
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 acid90%
13614-98-7

minocycline Hydrochloride

149934-16-7

(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
ConditionsYield
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;
1075240-45-7

C10H15Cl4NO3

13614-98-7

minocycline Hydrochloride

1075240-40-2

C32H42Cl2N4O9

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 24 - 40℃; for 24h; Tscherniac-Einhorn reaction;76%

Minocycline hydrochloride Specification

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.

5. Safety information of Minocycline hydrochloride
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
RIDADR: 3249
WGK Germany: 3
RTECS: QI7630500
HazardClass: 6.1(b)
PackingGroup:  III
Risk Statements: Irritating to the eyes;Irritating to the respiratory system;Irritating to the skin
Safety Statements: Wear suitable protective clothing
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and parenteral routes. Human systemic effects: dermatitis, eye effects, increased body temperature. When heated to decomposition it emits toxic fumes of NOx and HCl.

6. Uses of Minocycline hydrochloride
Minocycline hydrochloride (CAS NO.13614-98-7) is primarily used to treat acne and other skin infections as well as lyme disease as the one pill twice daily 100 mg dosage is far easier for patients than the four times a day required with tetracycline or oxytetracycline. It may be used to treat certain strains of MRSA infection and disease caused by drug resistant Acinetobacter. And it is mainly used as second generation tetracycline antibiotic and  antibacterial.

7. Production of Minocycline hydrochloride
You can get the Minocycline hydrochloride by using 6-demethyl chlortetracycline as raw material with the azo the salt derivatives law or esterification prepared minocycline.

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