• Name

  Metacycline hydrochloride

• EINECS 223-568-3
• CAS No. 3963-95-9
• Article Data1
• CAS DataBase
• Density
• Solubility
• Melting Point
• Formula C₂₂H₂₃ClN₂O₈
• Boiling Point 813.8 °C at 760 mmHg
• Molecular Weight 478.886
• Flash Point 445.9 °C
• Transport Information
• Appearance yellow crystalline powder
• Safety 24/25-22
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-,monohydrochloride (8CI);2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-,monohydrochloride, [4S-(4a,4aa,5a,5aa,12aa)]-;6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline hydrochloride;6-Demethyl-6-deoxy-6-methyleneoxytetracycline monohydrochloride;6-Methylene-5-hydroxytetracycline hydrochloride;6-Methyleneoxytetracyclinehydrochloride;Adriamicina;Ciclobiotic;Germiciclin;Londomycin;Metacyclinhydrochloride;Metadomus;Methacycline monohydrochloride;Metilenbiotic;Optimycin;Physiomycine;Rindex;
• PSA 181.62000
• LogP 1.06440

Synthetic route

3963-95-9

methacycline hydrochloride

A

564-25-0

doxycycline

B

3219-99-6

6-epidoxycycline

Conditions

Conditions	Yield
With hydrogen; closo-3,3-(η2,η3-C7H7CH2)-3,1,2-RhC2B9H11 In methanol at 43℃; under 76000 Torr; for 4h;	A 95.5% B 2%
With hydrogen; rhodium-carborane complex B In methanol at 100℃; under 76000 Torr; for 4h;	A 41% B 52.5%
With hydrogen; In methanol at 60℃; under 76000 Torr; for 4h;	A 96 % Chromat. B 2.5 % Chromat.
With hydrogen; In methanol at 60℃; under 76000 Torr; for 4h; Yield given. Yields of byproduct given;
With hydrogen; closo-(ϖ-cyclodienyl)rhodacarborane In methanol at 60℃; under 76000 Torr; for 4h; Product distribution; various catalyst;	A 96 % Chromat. B 2.5 % Chromat.

3963-95-9

methacycline hydrochloride

C10H16BO3

[4S-(4α,12aα)]-4-(dimethylamino)-6-(4-tert-butylbenzylidene)-3,5,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxamide

Conditions

Conditions	Yield
With copper dichloride In methanol Heating;	43%

3963-95-9

methacycline hydrochloride

6258-66-8

(4-chlorophenyl)methanethiol

13-<(4-chlorobenzyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 2h; Heating;	35.2%

3963-95-9

methacycline hydrochloride

75-33-2

2-propanethiol

13-(isopropylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	32.4%

1679-07-8

cyclopentylthiol

3963-95-9

methacycline hydrochloride

13-(cyclopentylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	32.1%

111-31-9

Hexanethiol

3963-95-9

methacycline hydrochloride

13-(hexylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	31.5%

513-44-0

2-methylpropanethiol-1

3963-95-9

methacycline hydrochloride

13-(isobutylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	29.5%

36480-40-7

3,4-dichlorobenzyl mercaptan

3963-95-9

methacycline hydrochloride

13-<(3,4-dichlorobenzyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 2h; Heating;	29.2%

108-98-5

thiophenol

3963-95-9

methacycline hydrochloride

13-(phenylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;	27.1%

3963-95-9

methacycline hydrochloride

100-53-8

phenylmethanethiol

146253-75-0

13-(benzylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 2h; Heating;	26%

3963-95-9

methacycline hydrochloride

106-54-7

p-Chlorothiophenol

13-<(4-chlorophenyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;	25.3%

107-03-9

1-thiopropane

3963-95-9

methacycline hydrochloride

13-(propylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	25%

109-79-5

1-butanethiol

3963-95-9

methacycline hydrochloride

13-(butylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	23%

3963-95-9

methacycline hydrochloride

75-08-1

ethanethiol

13-(ethylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	22.9%

17481-19-5

3-chloropropanethiol

3963-95-9

methacycline hydrochloride

13-(3-chloropropylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	21.4%

106-53-6

para-bromobenzenethiol

3963-95-9

methacycline hydrochloride

13-<(4-bromophenyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;	21%

96-27-5

rac-3-sulfanylpropane-1,2-diol

3963-95-9

methacycline hydrochloride

13-<(2,3-dihydroxypropyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	19.3%

3963-95-9

methacycline hydrochloride

60-24-2

2-hydroxyethanethiol

13-<(2'-hydroxyethyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
at 100℃; for 0.5h;	19.3%

696-63-9

4-Methoxybenzenethiol

3963-95-9

methacycline hydrochloride

13-<(4-methoxyphenyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;	18.9%

74-93-1

methylthiol

3963-95-9

methacycline hydrochloride

13-(methylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 70℃; for 4h;	18.4%

3963-95-9

methacycline hydrochloride

107-96-0

3-mercaptopropionic acid

13-<(2-carboxyethyl)thio>-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	17.3%

75-66-1

2-methylpropan-2-thiol

3963-95-9

methacycline hydrochloride

13-(tert-butylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 10h; Heating;	15.2%

1569-69-3

Cyclohexanethiol

3963-95-9

methacycline hydrochloride

13-(cyclohexylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	15%

143-10-2

decylthiol

3963-95-9

methacycline hydrochloride

13-(n-decylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	14.3%

3963-95-9

methacycline hydrochloride

541-31-1

3-methylbutanethiol

13-(isopentylthio)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;	11.3%

3963-95-9

methacycline hydrochloride

13-(benzylsulfonyl)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 26 percent / AIBN / ethanol / 2 h / Heating 2: 50 mg / 0.1M aq. oxone / ethanol / 1 h / Ambient temperature View Scheme

3963-95-9

methacycline hydrochloride

13-(cyclopentylthio)-5-hydroxy-6-α-deoxy-N-(morpholionemethyl)tetracycline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 32.1 percent / AIBN / ethanol / 12 h / Heating 2: 77.8 percent / 2-methyl-propan-2-ol; H2O / 1.) RT, 30 min, 2.) reflux, 15 min View Scheme

3963-95-9

methacycline hydrochloride

13-(benzylsulfinyl)-5-hydroxy-6-α-deoxytetracycline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 26 percent / AIBN / ethanol / 2 h / Heating 2: 35 percent / 0.1M aq. oxone / ethanol / 0.42 h / Ambient temperature View Scheme

methacycline p-toluene sulfonate

methacycline p-toluene sulfonate

3963-95-9

methacycline hydrochloride

doxycycline

chlorotris(triphenylphosphane)rhodium(I)

914-00-1, 138245-75-7

methacycline

104-15-4

toluene-4-sulfonic acid

3963-95-9

methacycline hydrochloride

doxycycline p-toluenesulphonate

Conditions

Conditions	Yield
With hydrazine In methanol

...Expand

Metacycline hydrochloride Chemical Properties

Metacycline hydrochloride Toxicity Data With Reference

Metacycline hydrochloride Safety Profile