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3963-95-9

Basic Information
CAS No.: 3963-95-9
Name: Metacycline hydrochloride
Article Data: 1
Molecular Structure:
Molecular Structure of 3963-95-9 (Metacycline hydrochloride)
Formula: C22H23ClN2O8
Molecular Weight: 478.886
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;
EINECS: 223-568-3
Boiling Point: 813.8 °C at 760 mmHg
Flash Point: 445.9 °C
Appearance: yellow crystalline powder
Safety: 24/25-22
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
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.
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol for 2h; Heating;26%
Downstream Products
564-25-0
3219-99-6
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Chemistry

Chemical Name: Metacycline hydrochloride
IUPAC NAME: (2Z,4S,4aR,5S,5aR,12aS)-2-[Amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride
CAS No: 3963-95-9
EINECS: 223-568-3
RTECS: QI9276000
Molecular Formula: C22H23ClN2O8
Molecular Weight: 478.88 g/mol
Polar Surface Area: 181.62 Å2
Flash Point: 445.9 °C
Enthalpy of Vaporization: 124.02 kJ/mol
Boiling Point: 813.8 °C at 760 mmHg
Vapour Pressure: 5.4E-28 mmHg at 25°C 
Methacycline hydrochloride (CAS NO.3963-95-9) is a tetracycline antibiotic.Following is the structure:


Product Categories: API
The chemical synonymous of Methacycline hydrochloride (CAS NO.3963-95-9) are 6-Demethyl-6-deoxy-6-methyleneoxytetracycline monohydrochloride ; 6-Demethyl-6-deoxy-6-methyleneoxytetracyclne hydrochloride ; Metacycline ; Metacycline Hcl ; Metacycline hydrochloride ; Methacycline Hcl ; Methacycline hydrochloride ; 12,12a-Pentahydroxy-6-methylene-1,11-dioxo-1monohydrochloride                                                 

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 288mg/kg (288mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
mouse LD50 intravenous 193mg/kg (193mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.
mouse LD50 oral 3450mg/kg (3450mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.
rat LD50 intraperitoneal 252mg/kg (252mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 202mg/kg (202mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.
rat LD50 oral > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. An antibacterial agent. When heated to decomposition it emits very toxic fumes of NOx and HCl.
Safety Statements: 24/25-22 
S24/25: Avoid contact with skin and eyes. 
S22: Do not breathe dust.
RTECS: QI9276000
Attention:
1. Storage: Store in a cool, dry place. Store in a tightly closed container.
2. Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.