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Basic Information

Molecular Structure:
CAS No.:	13614-98-7
Name:	Minocycline hydrochloride
Article Data:	6

Formula:	C₂₃H₂₇N₃O_7^.ClH
Molecular Weight:	493.944
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)-;
EINECS:	237-099-7
Melting Point:	205-210 °C(dec)
Boiling Point:	812.8 °C at 760 mmHg
Flash Point:	445.4 °C
Solubility:	Freely soluble in water
Appearance:	crystalline yellow powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
PSA:	164.63000
LogP:	1.68890

Synthetic route

: 10118-90-8
MINOCYCLINE

: 13614-98-7
minocycline Hydrochloride

Conditions

Conditions	Yield
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

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%

: 77-78-1
dimethyl sulfate

: 5679-00-5
7-amino-6-desmethyl-6-deoxytetracycline

: 13614-98-7
minocycline Hydrochloride

Conditions

Conditions	Yield
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

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%

: 50-00-0
formaldehyd

: 5679-00-5
7-amino-6-desmethyl-6-deoxytetracycline

: 13614-98-7
minocycline Hydrochloride

Conditions

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%

: C34H49N3O9Si

: 13614-98-7
minocycline Hydrochloride

Conditions

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

: 808-26-4, 2696-12-0, 15964-02-0, 39105-46-9
sancycline

: 13614-98-7
minocycline Hydrochloride

Conditions

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

: 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

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%

: 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

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;

: 1075240-45-7
C10H15Cl4NO3

: 13614-98-7
minocycline Hydrochloride

: 1075240-40-2
C32H42Cl2N4O9

Conditions

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

Downstream Products

10118-90-8

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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: Irritant

Xi
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 NO_x 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.