Product Name

  • Name

    Minocycline

  • EINECS 237-099-7
  • CAS No. 10118-90-8
  • Article Data14
  • CAS DataBase
  • Density 1.553 g/cm3
  • Solubility 52g/L(25 oC)
  • Melting Point
  • Formula C23H27N3O7
  • Boiling Point 659.401 °C at 760 mmHg
  • Molecular Weight 457.483
  • Flash Point 352.593 °C
  • Transport Information
  • Appearance Bright yellow-orange amorphous solid.
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 10118-90-8 (Minocycline)
  • Hazard Symbols
  • Synonyms 2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-(8CI);2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,[4S-(4a,4aa,5aa,12aa)]-;CL 59806;Dynacin;Minocyclin;Minocyn;Tri-minocycline;2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,(4S,4aS,5aR,12aS)-;
  • PSA 164.63000
  • LogP 0.88690

Synthetic route

3,10,12,12a- tetraacetylminocycline

3,10,12,12a- tetraacetylminocycline

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
With methanol; lithium hydroxide at 0 - 20℃; for 2h; Reagent/catalyst;93%
[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
149934-19-0

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
With nitrous acid isobutyl ester In N,N-dimethyl-formamide at 70℃; for 0.75h;85%
(dimethylamino)trimethyltin
993-50-0

(dimethylamino)trimethyltin

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
113164-67-3

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
dichlorobis(tri-O-tolylphosphine)palladium In toluene for 8h; Heating;68%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In N,N-dimethyl-formamide at 50℃; for 6h; Concentration; Reagent/catalyst;
minocycline Hydrochloride
13614-98-7

minocycline Hydrochloride

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
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;
morpholine
110-91-8

morpholine

(dimethylamino)trimethyltin
993-50-0

(dimethylamino)trimethyltin

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
113164-67-3

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide

A

MINOCYCLINE
10118-90-8

MINOCYCLINE

B

(4S,4aS,5aR,12aS)-4-Dimethylamino-3,10,12,12a-tetrahydroxy-7-morpholin-4-yl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-4-Dimethylamino-3,10,12,12a-tetrahydroxy-7-morpholin-4-yl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Stage #1: morpholine; (dimethylamino)trimethyltin In toluene Heating;
Stage #2: [4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide; dichlorobis(tri-O-tolylphosphine)palladium In toluene for 24h; Heating;
A n/a
B 42%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

(dimethylamino)trimethyltin
993-50-0

(dimethylamino)trimethyltin

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
113164-67-3

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide

A

MINOCYCLINE
10118-90-8

MINOCYCLINE

B

(4S,4aS,5aR,12aS)-4-Dimethylamino-3,10,12,12a-tetrahydroxy-7-(4-methyl-piperazin-1-yl)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-4-Dimethylamino-3,10,12,12a-tetrahydroxy-7-(4-methyl-piperazin-1-yl)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Stage #1: 1-methyl-piperazine; (dimethylamino)trimethyltin In toluene Heating;
Stage #2: [4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide; dichlorobis(tri-O-tolylphosphine)palladium In toluene for 24h; Heating;
A n/a
B 40%
azetidine
503-29-7

azetidine

(dimethylamino)trimethyltin
993-50-0

(dimethylamino)trimethyltin

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
113164-67-3

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide

A

MINOCYCLINE
10118-90-8

MINOCYCLINE

B

(4S,4aS,5aR,12aS)-7-Azetidin-1-yl-4-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-7-Azetidin-1-yl-4-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Stage #1: azetidine; (dimethylamino)trimethyltin In toluene Heating;
Stage #2: [4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide; dichlorobis(tri-O-tolylphosphine)palladium In toluene for 24h; Heating; Further stages.;
A 10%
B 35%
minocycline hydrochloride

minocycline hydrochloride

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water pH=8 - 9;
With sodium hydrogencarbonate In water pH=6.5 - 7;
demeclocycline hydrochloride
64-73-3

demeclocycline hydrochloride

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine; palladium on activated charcoal; hydrogen / ethanol
2: rhodium contaminated with carbon; hydrogen; toluene-4-sulfonic acid / methanol / -5 - 5 °C
3: sulfuric acid; N-iodo-succinimide / 2 h / 0 - 10 °C
4: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 6 h / 50 °C
View Scheme
6-demethyltetracycline
987-02-0

6-demethyltetracycline

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: rhodium contaminated with carbon; hydrogen; toluene-4-sulfonic acid / methanol / -5 - 5 °C
2: sulfuric acid; N-iodo-succinimide / 2 h / 0 - 10 °C
3: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 6 h / 50 °C
View Scheme
demethylchlortetracycline hydrochloride

demethylchlortetracycline hydrochloride

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid; potassium nitrate / 1 h / Cooling with ice
2: potassium hydroxide / 4 h / 100 °C / Sealed tube
3: sodium hydroxide; urea; 5%-palladium/activated carbon; hydrogen / water / 6 h / 20 °C / 5250.53 Torr / Autoclave
4: hydrogen; methanesulfonic acid; 5% rhodium-on-charcoal / N,N-dimethyl-formamide; methanol / 7 h / 50 °C / 5250.53 - 6000.6 Torr / Autoclave
5: nitrous acid isobutyl ester / N,N-dimethyl-formamide / 0.75 h / 70 °C
View Scheme
9-nitrodemeclocycline

9-nitrodemeclocycline

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide / 4 h / 100 °C / Sealed tube
2: sodium hydroxide; urea; 5%-palladium/activated carbon; hydrogen / water / 6 h / 20 °C / 5250.53 Torr / Autoclave
3: hydrogen; methanesulfonic acid; 5% rhodium-on-charcoal / N,N-dimethyl-formamide; methanol / 7 h / 50 °C / 5250.53 - 6000.6 Torr / Autoclave
4: nitrous acid isobutyl ester / N,N-dimethyl-formamide / 0.75 h / 70 °C
View Scheme
6-hydroxy-9-nitrominocycline

6-hydroxy-9-nitrominocycline

MINOCYCLINE
10118-90-8

MINOCYCLINE

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; urea; 5%-palladium/activated carbon; hydrogen / water / 6 h / 20 °C / 5250.53 Torr / Autoclave
2: hydrogen; methanesulfonic acid; 5% rhodium-on-charcoal / N,N-dimethyl-formamide; methanol / 7 h / 50 °C / 5250.53 - 6000.6 Torr / Autoclave
3: nitrous acid isobutyl ester / N,N-dimethyl-formamide / 0.75 h / 70 °C
View Scheme
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
118-29-6

2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

MINOCYCLINE
10118-90-8

MINOCYCLINE

C41H37N5O11

C41H37N5O11

Conditions
ConditionsYield
Stage #1: 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione; MINOCYCLINE With hydrogenchloride; sulfuric acid; trifluoroacetic acid at 40 - 50℃; Inert atmosphere;
Stage #2: With monomethanolamine
97%
MINOCYCLINE
10118-90-8

MINOCYCLINE

minocycline Hydrochloride
13614-98-7

minocycline Hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 5℃; for 1h; pH=1 - 2; Solvent;92.7%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

MINOCYCLINE
10118-90-8

MINOCYCLINE

10-trifluoromethylsulfonate-minocycline
1035978-88-1

10-trifluoromethylsulfonate-minocycline

Conditions
ConditionsYield
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃;
90%
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran for 0.75h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; for 3h;
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 0.666667h; Schlenk technique; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide With dmap In tetrahydrofuran Schlenk technique; Inert atmosphere;
MINOCYCLINE
10118-90-8

MINOCYCLINE

C21H20N2O8

C21H20N2O8

Conditions
ConditionsYield
Stage #1: MINOCYCLINE With mercury(II) diacetate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve;
Stage #2: With dipotassium hydrogenphosphate; water; edetate disodium In N,N-dimethyl-formamide; acetonitrile at 0 - 5℃; for 0.583333h;
87.5%
MINOCYCLINE
10118-90-8

MINOCYCLINE

4-((-8-(dimethylamino)-5-hydroxy-4-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienecarboxamide

4-((-8-(dimethylamino)-5-hydroxy-4-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienecarboxamide

Conditions
ConditionsYield
With mercury(II) diacetate; sodium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 20℃; for 1h; Molecular sieve;22%
MINOCYCLINE
10118-90-8

MINOCYCLINE

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

10-methoxy-minocycline trifluoroacetate

10-methoxy-minocycline trifluoroacetate

Conditions
ConditionsYield
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran at -78 - 20℃; for 0.916667h; Schlenk technique; Inert atmosphere;
Stage #2: methyl p-toluene sulfonate In tetrahydrofuran Schlenk technique; Inert atmosphere;
Stage #3: trifluoroacetic acid In water; acetonitrile
17.4%
chloro-methylsulfanyl-methane
2373-51-5

chloro-methylsulfanyl-methane

MINOCYCLINE
10118-90-8

MINOCYCLINE

N2-Methyl-7-dimethylamino-6-deoxytetracyclin

N2-Methyl-7-dimethylamino-6-deoxytetracyclin

Conditions
ConditionsYield
(i) MeSO3H, (ii) Raney-Ni, aq. EtOH; Multistep reaction;
MINOCYCLINE
10118-90-8

MINOCYCLINE

C21H20N2O8(1-)
135513-28-9

C21H20N2O8(1-)

Conditions
ConditionsYield
With potassium hexacyanoferrate(III) In water pH 8.5 buffer;
MINOCYCLINE
10118-90-8

MINOCYCLINE

A

C21H20N2O8(1-)
135513-28-9

C21H20N2O8(1-)

B

C21H19N2O8(2-)
135535-66-9

C21H19N2O8(2-)

Conditions
ConditionsYield
With potassium hexacyanoferrate(III) In water Mechanism; Rate constant; Equilibrium constant; various pH;
MINOCYCLINE
10118-90-8

MINOCYCLINE

C21H19N2O8(2-)
135535-66-9

C21H19N2O8(2-)

Conditions
ConditionsYield
With potassium hexacyanoferrate(III) In water pH 14 buffer;
MINOCYCLINE
10118-90-8

MINOCYCLINE

A

7-hydroxy-6-deoxy-6-demethyltetracycline
61650-68-8

7-hydroxy-6-deoxy-6-demethyltetracycline

B

(4S,4aS,5aR,12aS)-4-Dimethylamino-3,12,12a-trihydroxy-1,7,10,11-tetraoxo-1,4,4a,5,5a,6,7,10,11,12a-decahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-4-Dimethylamino-3,12,12a-trihydroxy-1,7,10,11-tetraoxo-1,4,4a,5,5a,6,7,10,11,12a-decahydro-naphthacene-2-carboxylic acid amide

C

((4aS,11aR,12aS)-3-Carbamoyl-2,4a,5-trihydroxy-4,6,7,10-tetraoxo-4a,6,7,10,11,11a,12,12a-octahydro-4H-naphthacen-1-ylidene)-dimethyl-ammonium

((4aS,11aR,12aS)-3-Carbamoyl-2,4a,5-trihydroxy-4,6,7,10-tetraoxo-4a,6,7,10,11,11a,12,12a-octahydro-4H-naphthacen-1-ylidene)-dimethyl-ammonium

Conditions
ConditionsYield
With MES buffer; dihydrogen peroxide; potassium iodide; porcine thyroid peroxidase In water at 22℃; for 0.133333h; pH=6.5; Kinetics; Product distribution; Further Variations:; Catalysts; Reagents; Temperatures; reaction time; Enzymatic reaction;
MINOCYCLINE
10118-90-8

MINOCYCLINE

(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
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
With sulfuric acid; nitric acid at 0℃; for 1h;
MINOCYCLINE
10118-90-8

MINOCYCLINE

(4S,4aS,5aR,12aS)-4,7-Bis-dimethylamino-3,10,12,12a-tetrahydroxy-9-methanesulfonylamino-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-4,7-Bis-dimethylamino-3,10,12,12a-tetrahydroxy-9-methanesulfonylamino-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3; H2SO4 / 1 h / 0 °C
2: H2 / Pd/C / 2068.59 Torr
3: Na2CO3 / tetrahydrofuran
View Scheme
MINOCYCLINE
10118-90-8

MINOCYCLINE

(4S,4aS,5aR,12aS)-9-Benzenesulfonylamino-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-9-Benzenesulfonylamino-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3; H2SO4 / 1 h / 0 °C
2: H2 / Pd/C / 2068.59 Torr
3: Na2CO3 / tetrahydrofuran
View Scheme
MINOCYCLINE
10118-90-8

MINOCYCLINE

(4S,4aS,5aR,12aS)-9-(4-Bromo-butyrylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide
737733-50-5

(4S,4aS,5aR,12aS)-9-(4-Bromo-butyrylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3; H2SO4 / 1 h / 0 °C
2: H2 / Pd/C / 2068.59 Torr
3: DMPU
View Scheme
MINOCYCLINE
10118-90-8

MINOCYCLINE

(4S,4aS,5aR,12aS)-4,7-Bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-(thiophene-2-sulfonylamino)-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-4,7-Bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-(thiophene-2-sulfonylamino)-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3; H2SO4 / 1 h / 0 °C
2: H2 / Pd/C / 2068.59 Torr
3: Na2CO3 / tetrahydrofuran
View Scheme
MINOCYCLINE
10118-90-8

MINOCYCLINE

(4S,4aS,5aR,12aS)-4,7-Bis-dimethylamino-9-(4-dimethylamino-butyrylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-4,7-Bis-dimethylamino-9-(4-dimethylamino-butyrylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HNO3; H2SO4 / 1 h / 0 °C
2: H2 / Pd/C / 2068.59 Torr
3: DMPU
View Scheme
MINOCYCLINE
10118-90-8

MINOCYCLINE

(4S,4aS,5aR,12aS)-9-(4-Chloro-benzenesulfonylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

(4S,4aS,5aR,12aS)-9-(4-Chloro-benzenesulfonylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3; H2SO4 / 1 h / 0 °C
2: H2 / Pd/C / 2068.59 Torr
3: Na2CO3 / tetrahydrofuran
View Scheme

Minocycline Specification

1. Introduction of Minocycline
Minocycline is one kind of light yellow irregular solid or bright yellow-orange amorphous solid. The IUPAC Name of this chemical is (2Z,4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione. Besides, Minocycline belongs to antibiotics. In addition, its Classification Code is Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Drug / Therapeutic Agent; Human Data; Mutation data; Natural Product. Minocycline is the most lipid-soluble of the tetracycline-class antibiotics.

2. Properties of Minocycline
Physical properties about Minocycline are:
(1)Flash Point: 445.4 °C; (2)Boiling Point: 812.8 °C at 760 mmHg; (3)Enthalpy of Vaporization: 123.88 kJ/mol; (4)Vapour Pressure: 6.33E-28 mmHg at 25°C; (5)XLogP3: -0.6; (6)H-Bond Donor: 5; (7)H-Bond Acceptor: 9.

3. Structure Descriptors of Minocycline
(1)InChI: InChI=1S/C23H27N3O7/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)/t9-,11-,17-,23-/m0/s1
(2)InChIKey: FFTVPQUHLQBXQZ-KVUCHLLUSA-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
(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
(5)Smiles: [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

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant TDLo oral 12mg/kg/2D-I (12mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE

GASTROINTESTINAL: NAUSEA OR VOMITING
Therapie. Vol. 38, Pg. 93, 1983.
man TDLo oral 343mg/kg/17W- (343mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: LIVER FUNCTION TESTS IMPAIRED

BLOOD: EOSINOPHILIA
American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996.
mouse LD50 intracrebral 38mg/kg (38mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES
Chemotherapy Vol. 26, Pg. 196, 1980.
mouse LD50 intraperitoneal 310mg/kg (310mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
mouse LD50 intravenous 140mg/kg (140mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
mouse LD50 oral 3100mg/kg (3100mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
women TDLo oral 8mg/kg (8mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" American Journal of Medicine. Vol. 109, Pg. 340, 2000.
women TDLo oral 28mg/kg/2W-I (28mg/kg) BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)"

BEHAVIORAL: HEADACHE

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE
Annals of Internal Medicine. Vol. 127, Pg. 168, 1997.
women TDLo oral 100mg/kg (100mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: PROTEINURIS
British Medical Journal. Vol. 1, Pg. 524, 1979.
women TDLo oral 112mg/kg/4W-I (112mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996.
women TDLo oral 730mg/kg/1Y-I (730mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: LIVER FUNCTION TESTS IMPAIRED
American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996.
women TDLo oral 1204mg/kg/86W (1204mg/kg) MUSCULOSKELETAL: JOINTS British Journal of Rheumatology. Vol. 33, Pg. 674, 1994.
women TDLo oral 17520mg/kg/12 (17520mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Ophthalmology. Vol. 125, Pg. 396, 1998.

5. Safety information of Minocycline
Poison by intraperitoneal, intravenous, and intracerebral routes. Moderately toxic by ingestion. Human systemic effects by ingestion: interstitial nephritis, proteinuris and hematuris. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

First Aid Measures:
Ingestion: Seek medical attention. If individual is drowsy or unconscious, do not give anything by mouth; place individual on the left side with the head down. Contact a physician, medical facility, or poison control center for advice about whether to induce vomiting. If possible, do not leave individual unattended.
Inhalation: If symptoms develop, move individual away from exposure and into fresh air. If symptoms persist, seek medical attention. If breathing is difficult, administer oxygen. Keep person warm and quiet; seek immediate medical attention.
Skin: Remove contaminated clothing. Wash exposed area with soap and water. If symptoms persist, seek medical attention. Launder clothing before reuse.
Eyes: If symptoms develop, immediately move individual away from exposure and into fresh air. Flush eyes gently with water for at least 15 minutes while holding eyelids apart; seek immediate medical attention.
Handling and Storage:
Storage: Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
Handling: All chemicals should be considered hazardous. Avoid direct physical contact. Use appropriate, approved safety equipment. Untrained individuals should not handle this chemical or its container. Handling should occur in a chemical fume hood.

6. Uses of Minocycline
Minocycline (10118-90-8) can be used in medication. It is a bacteriostatic antibiotic, classified as a long-acting type. Minocycline is a relatively poor tetracycline-class antibiotic choice for urinary pathogens sensitive to this antibiotic class, as its solubility in water and levels in the urine are less than all other tetracyclines. Minocycline is metabolized by the liver and has poor urinary excretion. Minocycline is not a naturally-occurring antibiotic, but was synthesized semi-synthetically from natural tetracycline antibiotics.

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