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64-75-5

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Basic Information
CAS No.: 64-75-5
Name: 2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,hydrochloride (1:1), (4S,4aS,5aS,6S,12aS)-
Article Data: 4
Cas Database
Molecular Structure:
Molecular Structure of 64-75-5 (2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,hydrochloride (1:1), (4S,4aS,5aS,6S,12aS)-)
Formula: C22H24N2O8.HCl
Molecular Weight: 480.902
Synonyms: Neocycline B;Paltet;Panmycin hydrochloride;Partrex;Polyotic ointment;Purocyclina;Remicyclin;Riocyclin;Robitet;Subamycin;Supramycin;Tefilin;Tet-Cy;Tetrabakat;Tetrabid;Tetrabon;Tetrachel;Tetracompren;Tetracycline hydrochloride;Tetracyn;Tetralution;Tetrosol;Triphacyclin;Unicin;Vetquamycin 324;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride (8CI);Achro;Achromycin hydrochloride;Ala-Tet;Ambracyn;Bristacycline;Cancycline-250;Criseociclina;Dumocyclin;Helvecyclin;Hostacycline;Medamycin;Tetracycline HCL;
EINECS: 200-593-8
Density: N/A
Melting Point: 220-223 °C(lit.)
Boiling Point: 799.4 °C at 760 mmHg
Flash Point: 437.3 °C
Solubility: 50 g/L in water
Appearance: Yellow crystalline powder
Hazard Symbols: IrritantXi, HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 26-36
Transport Information: N/A
PSA: 181.62000
LogP: 1.28790
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Synthetic route
60-54-8

TETRACYCLINE

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water
32359-20-9

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10.5 h / 23 °C / Inert atmosphere
2.1: methanol; hexane; benzene / 0.08 h / 23 °C / Inert atmosphere
2.2: 0.5 h
3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere
4.2: 18 h / 23 °C / Inert atmosphere
5.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere
5.2: 23 h / 0 - 23 °C / Inert atmosphere
6.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
7.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
8.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
8.2: 0.42 h / 0 °C / Inert atmosphere
9.1: 48 h / 85 °C / Inert atmosphere
10.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
11.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
12.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
12.2: air
13.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
13.2: Inert atmosphere
View Scheme
367954-24-3

(1S,2R,3S,6R)-2,3-Dihydroxy-7-oxa-bicyclo[4.1.0]hept-4-ene-3-carboxylic acid

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: methanol; hexane; benzene / 0.08 h / 23 °C / Inert atmosphere
1.2: 0.5 h
2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere
3.2: 18 h / 23 °C / Inert atmosphere
4.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere
4.2: 23 h / 0 - 23 °C / Inert atmosphere
5.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
6.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
7.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
7.2: 0.42 h / 0 °C / Inert atmosphere
8.1: 48 h / 85 °C / Inert atmosphere
9.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
10.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
11.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
11.2: air
12.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
12.2: Inert atmosphere
View Scheme
367954-37-8

(1S,2R,3R,6S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-4-ene-1-carboxylic acid methyl ester

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere
2.2: 18 h / 23 °C / Inert atmosphere
3.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere
3.2: 23 h / 0 - 23 °C / Inert atmosphere
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
5.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
6.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
6.2: 0.42 h / 0 °C / Inert atmosphere
7.1: 48 h / 85 °C / Inert atmosphere
8.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
9.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
10.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
10.2: air
11.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
11.2: Inert atmosphere
View Scheme
852821-12-6

3-benzyloxy-5-dimethylaminomethylisoxazole

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere
2.2: 18 h / 23 °C / Inert atmosphere
3.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere
3.2: 23 h / 0 - 23 °C / Inert atmosphere
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
5.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
6.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
6.2: 0.42 h / 0 °C / Inert atmosphere
7.1: 48 h / 85 °C / Inert atmosphere
8.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
9.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
10.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
10.2: air
11.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
11.2: Inert atmosphere
View Scheme
90109-84-5

C6H9BrN2O

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: sodium / 32 h / 23 °C / Inert atmosphere
1.2: 20 h / 23 - 120 °C / Inert atmosphere
2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere
3.2: 18 h / 23 °C / Inert atmosphere
4.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere
4.2: 23 h / 0 - 23 °C / Inert atmosphere
5.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
6.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
7.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
7.2: 0.42 h / 0 °C / Inert atmosphere
8.1: 48 h / 85 °C / Inert atmosphere
9.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
10.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
11.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
11.2: air
12.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
12.2: Inert atmosphere
View Scheme

C32H50N2O6Si2

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere
1.2: 18 h / 23 °C / Inert atmosphere
2.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere
2.2: 23 h / 0 - 23 °C / Inert atmosphere
3.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
4.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
5.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
5.2: 0.42 h / 0 °C / Inert atmosphere
6.1: 48 h / 85 °C / Inert atmosphere
7.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
8.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
9.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
9.2: air
10.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
10.2: Inert atmosphere
View Scheme
852821-14-8

C26H36N2O6Si

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere
1.2: 23 h / 0 - 23 °C / Inert atmosphere
2.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
3.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
4.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
4.2: 0.42 h / 0 °C / Inert atmosphere
5.1: 48 h / 85 °C / Inert atmosphere
6.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
7.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
8.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
8.2: air
9.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
9.2: Inert atmosphere
View Scheme
852821-15-9

C26H36N2O5Si

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere
2.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
3.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
3.2: 0.42 h / 0 °C / Inert atmosphere
4.1: 48 h / 85 °C / Inert atmosphere
5.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
6.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
7.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
7.2: air
8.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
8.2: Inert atmosphere
View Scheme
870288-27-0

C20H22N2O5

64-75-5

tetracycline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere
2.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere
2.2: 0.42 h / 0 °C / Inert atmosphere
3.1: 48 h / 85 °C / Inert atmosphere
4.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
5.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere
6.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere
6.2: air
7.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr
7.2: Inert atmosphere
View Scheme
Raw Materials
60-54-8
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60-54-8
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Tetracycline hydrochloride is an organic compound with the formula C22H24N2O8.HCl. The systematic name of this chemical is (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride (1:1). With the CAS registry number 64-75-5, it is also named as 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-, hydrochloride (1:1). The product's categories are Active Pharmaceutical Ingredients; Antibiotics for Research and Experimental Use; Biochemistry; Others (Antibiotics for Research and Experimental Use); Antibiotic Explorer; TA - TEAntibiotics; Tetracyclines Antibiotics; Bacteriostatic Antibiotics; Chemical Structure; L - ZAlphabetic; Principle; TetracyclinesMore...Close...; Antibacterial; Antibiotics; Interferes with Protein Synthesis Spectrum of Activity;L - ZAntibiotics; Mechanism of Action; Antibiotics T-ZAntibiotics; Antibiotics Antibiotics; Antibiotics Research Essentials; Antibiotics A to; Antibiotics by Application; Cell Culture; Chemical Structure Class; Core Bioreagents; Genetic Marker Selection Antibiotics; Reagents and Supplements; Tetracyclines; Research Essentials. Besides, it is a yellow crystalline powder, which is a broad-spectrum polyketide antibiotic produced by the streptomyces genus of actinobacteria.

Physical properties about Tetracycline hydrochloride are:
(1)# of Rule of 5 Violations: 2; (2)ACD/LogD (pH 5.5): -4; (3)ACD/LogD (pH 7.4): -4; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 10; (9)#H bond donors: 7; (10)#Freely Rotating Bonds: 7; (11)Polar Surface Area: 181.62 Å2; (12)Flash Point: 437.3 °C; (13)Enthalpy of Vaporization: 121.9 kJ/mol; (14)Boiling Point: 799.4 °C at 760 mmHg; (15)Vapour Pressure: 5.82E-27 mmHg at 25°C.


Safety information of Tetracycline hydrochloride:
When you are using this chemical, please be cautious about it as the following:It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.CN(C)[C@@H]2C(\O)=C(\C(N)=O)C(=O)[C@@]3(O)C(/O)=C4/C(=O)c1c(cccc1O)[C@@](C)(O)[C@H]4C[C@@H]23
(2)InChI: InChI=1/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1
(3)InChIKey: XMEVHPAGJVLHIG-FMZCEJRJBJ
(4)Std. InChI: InChI=1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1
(5)Std. InChIKey: XMEVHPAGJVLHIG-FMZCEJRJSA-N

The toxicity data of Tetracycline hydrochloride is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 200mg/kg/7D-I (200mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE Clinical Pharmacy. Vol. 4, Pg. 455, 1985.
mouse LD50 intraperitoneal 368mg/kg (368mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 16, Pg. 33, 1964.
mouse LD50 intravenous 157mg/kg (157mg/kg)   Farmaco, Edizione Scientifica. Vol. 10, Pg. 197, 1955.
mouse LD50 oral 2759mg/kg (2759mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 16, Pg. 33, 1964.
mouse LD50 unreported 105mg/kg (105mg/kg)   "Evaluation of Embryotoxicity, Mutagenicity and Carcinogenicity Risks In New Drugs, Proceedings of the Symposium on Toxicological Testing for Safety of New Drugs, 3rd, Prague, 1976," Benesova, O., et al., eds., Prague, Czechoslovakia, Univerzita Karlova, 1979Vol. -, Pg. 55, 1979.
rabbit LDLo intrapleural 35mg/kg (35mg/kg) LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Lung. Vol. 174, Pg. 373, 1996.
rat LD50 intraperitoneal 318mg/kg (318mg/kg)   Gendai no Rinsho. Vol. 2, Pg. 26, 1968.
rat LD50 intravenous 128mg/kg (128mg/kg)   Farmaco, Edizione Scientifica. Vol. 10, Pg. 197, 1955.
rat LD50 oral 6443mg/kg (6443mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous 700mg/kg (700mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Toxicology and Applied Pharmacology. Vol. 9, Pg. 445, 1966.