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Name	Metacycline hydrochloride	EINECS	223-568-3
CAS No.	3963-95-9	Density	N/A
PSA	181.62000	LogP	1.06440
Solubility	N/A	Melting Point	N/A
Formula	C₂₂H₂₃ClN₂O₈	Boiling Point	813.8 °C at 760 mmHg
Molecular Weight	478.886	Flash Point	445.9 °C
Transport Information	N/A	Appearance	yellow crystalline powder
Safety	24/25-22	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	1

Metacycline hydrochloride 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%

Metacycline hydrochloride Chemical Properties

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

Metacycline hydrochloride Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	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.

Metacycline hydrochloride 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 NO_x 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.

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