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Metacycline hydrochloride
Cas No: 3963-95-9
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High quality Metacycline Hydrochloride supplier in China
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API Price 99% Metacycline hydrochloride /hcl powder CAS:3963-95-9
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Methacycline hydrochloride
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Methacycline hydrochloride
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Metacylcline HLC CAS 3963-95-9
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Metacycline hydrochloride
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USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Enke Pharma-tech Co.,Ltd. (Cangzhou, China ) Contact Supplier
Supplies Metacycline hydrochloride Raw Material Powder CAS 3963-95-9
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3963-95-9 Usage

Originator

Rondomycin ,Pfizer ,UK ,1963

Therapeutic Function

Antibiotic

Brand name

Rondomycin (Medpointe).

Uses

A broad spectrum, anti bacterial, semisynthetic antibiotic related to Tetracycline

General Description

The synthesis of methacycline, 6-deoxy-6-demethyl-6-methylene-5-oxytetracycline hydrochloride (Rondomycin), reportedby Blackwood et al. in 1961, was accomplished bychemical modification of oxytetracycline. It has an antibioticspectrum like that of the other tetracyclines but greater potency;about 600 mg of methacycline is equivalent to 1 g oftetracycline. Its particular value lies in its longer serum halflife;doses of 300 mg produce continuous serum antibacterialactivity for 12 hours. Its toxic manifestations and contraindicationsare similar to those of the other tetracyclines.The greater stability of methacycline, both in vivo and invitro, results from modification at C-6. Removal of the 6-hydroxy group markedly increases the stability of ring C toboth acids and bases, preventing the formation of isotetracyclinesby bases. Anhydrotetracyclines still can form, however,by acid-catalyzed isomerization under strongly acidicconditions. Methacycline hydrochloride is a yellow to darkyellow, crystalline powder that is slightly soluble in waterand insoluble in nonpolar solvents. It should be stored intight, light-resistant containers in a cool place.

Uses

Broad spectrum, semisynthetic antibiotic related to Tetracycline. Antibacterial.

Chemical Properties

yellow crystalline powder

Uses

analgesic, narcotic antagonist

Manufacturing Process

To a stirred solution of 4.6 g (0.01 mol) of anhydrous oxytetracycline in 40 ml of dry tetrahydrofuran is added 3.5 g (0.021 mol) of pyridine-sulfur trioxide complex. After 16 hours of stirring at room temperature, the resulting suspension is filtered, and the solid is slurried with 25 ml of 2% hydrochloric acid for 10 minutes, filtered and thoroughly washed with methanol followed by ether. The pale yellow crystalline 5-oxytetracycline-6,12-hemiketal-12-sulfuric acid ester melts at 210°C.500 mg 5-oxytetracycline-6,12-hemiketal-12-sulfuric acid ester, prepared as described, is added to 4 ml dry liquid hydrogen fluoride, and the mixture is stirred for 1.5 hours at ice bath temperature. The hydrogen fluoride is then evaporated in a stream of nitrogen and the resulting gummy solids are triturated with about 15 ml ether and filtered. The resulting solid hydrofluoride salt is further purified by suspending in water, adjusting the pH to about 4, and extracting the 6-methylene-5-oxytetracycline free base from the aqueous phase with ethyl acetate. The extract is separated and evaporated to dryness under reduced pressure. The resulting residue is triturated with ether and filtered, and the solid is recrystallized from methanol-acetone-etherconcentrated hydrochloric acid to obtain the product as a purified hydrochloride, according to US Patent 3,026,354.

Uses

Methacycline hydrochloride is a salt prepared from methacycline taking advantage of the basic dimethylamino group which protonates and readily forms a salt in hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Like all tetracyclines, methacycline hydrochloride shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis.
InChI:InChI=1/C22H22N2O8.ClH/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31);1H

3963-95-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1397006)  Methacyclinehydrochloride  United States Pharmacopeia (USP) Reference Standard 3963-95-9 1397006-200MG 4,662.45CNY Detail

3963-95-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Metacycline hydrochloride

1.2 Other means of identification

Product number -
Other names londomycin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3963-95-9 SDS

3963-95-9Synthetic route

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

A

doxycycline
564-25-0

doxycycline

B

6-epidoxycycline
3219-99-6

6-epidoxycycline

Conditions
ConditionsYield
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.
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

C10H16BO3

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

[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
ConditionsYield
With copper dichloride In methanol Heating;43%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

(4-chlorophenyl)methanethiol
6258-66-8

(4-chlorophenyl)methanethiol

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 2h; Heating;35.2%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

2-propanethiol
75-33-2

2-propanethiol

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;32.4%
cyclopentylthiol
1679-07-8

cyclopentylthiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;32.1%
Hexanethiol
111-31-9

Hexanethiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;31.5%
2-methylpropanethiol-1
513-44-0

2-methylpropanethiol-1

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;29.5%
3,4-dichlorobenzyl mercaptan
36480-40-7

3,4-dichlorobenzyl mercaptan

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 2h; Heating;29.2%
thiophenol
108-98-5

thiophenol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;27.1%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

phenylmethanethiol
100-53-8

phenylmethanethiol

13-(benzylthio)-5-hydroxy-6-α-deoxytetracycline
146253-75-0

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 2h; Heating;26%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;25.3%
1-thiopropane
107-03-9

1-thiopropane

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;25%
1-butanethiol
109-79-5

1-butanethiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;23%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

ethanethiol
75-08-1

ethanethiol

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;22.9%
3-chloropropanethiol
17481-19-5

3-chloropropanethiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;21.4%
para-bromobenzenethiol
106-53-6

para-bromobenzenethiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;21%
rac-3-sulfanylpropane-1,2-diol
96-27-5

rac-3-sulfanylpropane-1,2-diol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;19.3%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

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

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

Conditions
ConditionsYield
at 100℃; for 0.5h;19.3%
4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 6h; Heating;18.9%
methylthiol
74-93-1

methylthiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol at 70℃; for 4h;18.4%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;17.3%
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 10h; Heating;15.2%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;15%
decylthiol
143-10-2

decylthiol

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;14.3%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

3-methylbutanethiol
541-31-1

3-methylbutanethiol

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

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

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 12h; Heating;11.3%
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
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
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
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
methacycline hydrochloride
3963-95-9

methacycline hydrochloride

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

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

Conditions
ConditionsYield
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

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

doxycycline

doxycycline

chlorotris(triphenylphosphane)rhodium(I)

chlorotris(triphenylphosphane)rhodium(I)

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

methacycline hydrochloride
3963-95-9

methacycline hydrochloride

doxycycline p-toluenesulphonate

doxycycline p-toluenesulphonate

Conditions
ConditionsYield
With hydrazine In methanol

3963-95-9Upstream product

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