3D Mol Similar

Minocycline hydrochloride

: Iupac Name：(4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide;hydrochloride; CAS No.: 13614-98-7; Molecular Weight：493.941; Modify Date.: 2022-11-22 15:40; Introduction: Minocycline, 7-dimethylamino-6-demethyl-6-deoxytetracycline(Minocin, Vectrin), the most potent tetracycline currentlyused in therapy, is obtained by reductive methylationof 7-nitro-6-demethyl-6-deoxytetracycline. It was releasedfor use in the United States in 1971. Because minocycline,like doxycycline, lacks the 6-hydroxyl group, it is stablein acids and does not dehydrate or rearrange to anhydroor lactone forms. Minocycline is well absorbed orally togive high plasma and tissue levels. It has a very long serumhalf-life, resulting from slow urinary excretion and moderateprotein binding. Doxycycline and minocycline, alongwith oxytetracycline, show the least in vitro calcium bindingof the clinically available tetracyclines. The improved distributionproperties of the 6-deoxytetracyclines have been attributedto greater lipid solubility.Perhaps the most outstanding property of minocyclineis its activity toward Gram-positive bacteria, especiallystaphylococci and streptococci. In fact, minocycline hasbeen effective against staphylococcal strains that are resistantto methicillin and all other tetracyclines, includingdoxycycline. Although it is doubtful that minocyclinewill replace bactericidal agents for the treatment of lifethreateningstaphylococcal infections, it may become auseful alternative for the treatment of less serious tissueinfections. Minocycline has been recommended for thetreatment of chronic bronchitis and other upper respiratorytract infections. Despite its relatively low renal clearance,partially compensated for by high serum and tissuelevels, it has been recommended for the treatment of urinary tract infections. It has been effective in the eradicationof N. meningitidis in asymptomatic carriers. View more+

Request For Quotation

1. Names and Identifiers

: 1.1 Name; Minocycline hydrochloride; 1.2 Synonyms; (4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide hydrochloride (1:1) (4S,4aS,5aR,12aS)-4,7-Bis(diMethylaMino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxaMide hydrochloride (4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride (1:1) [4S-(4a,4aa,5aa,12aa)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide Monohydrochloride [4S-(4alpha,4aalpha,5aalpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-te [4S-(4alpha,4aalpha,5aalpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxonaphthacene-2-carboxamide monohydrochloride 10,12,12a-tetrahydroxy-1,11-dioxo--monohydrochloride 2-(Amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4,4a,5,5a,6,12a-hexahydrotetracene-1,3,12-trione hydrochloride 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-, hydrochloride (1:1) 2-naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-, monohydrochloride 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, hydrochloride (1:1), (4S,4aS,5aR,12aS)- 7-Dimethylamino-6-demethyl-6-deoxytetracycline Monohydrochloride Arestin Dynacin EINECS 237-099-7 Klinomycin KlinoMycin, Minocycline chloride, MinoMycin, NSC 141993 MFCD00083669 Minocin Minocycline (hydrochloride) MINOCYCLINE HCL Minocycline hydrochloride Solution, 100ppm Minocyn VECTRIN; View all

1.3 CAS No.: 13614-98-7

1.4 CID: 54685925

1.5 EINECS(EC#): 237-099-7

1.6 Molecular Formula: C23H28ClN3O7 (isomer)

1.7 Inchi: InChI=1S/C23H27N3O7.ClH/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28;/h5-6,9,11,17,27-28,31,33H,7-8H2,1-4H3,(H2,24,32);1H/t9-,11-,17-,23-;/m0./s1

1.8 InChIkey: WTJXVDPDEQKTCV-VQAITOIOSA-N

1.9 Canonical Smiles: CN(C)C1C2CC3CC4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C.Cl

1.10 Isomers Smiles: CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C.Cl

2. Properties

2.1 Density: 1.0170

2.1 Melting point: 205-210oC(dec)

2.1 Boiling point: 659.4°Cat760mmHg

2.1 Flash Point: 352.6°C

2.1 Precise Quality: 493.16200

2.1 PSA: 164.63000

2.1 logP: 1.68890

2.1 Appearance: crystalline yellow

2.2 Storage: 2-8°C

2.3 Chemical Properties: Yellow Crystalline Powder

2.4 Color/Form: yellow

2.5 Water Solubility: In water, 52,000 mg/l at 25 deg C.

2.6 Stability: Light Sensitive

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 General Description: Minocycline, 7-dimethylamino-6-demethyl-6-deoxytetracycline(Minocin, Vectrin), the most potent tetracycline currentlyused in therapy, is obtained by reductive methylationof 7-nitro-6-demethyl-6-deoxytetracycline. It was releasedfor use in the United States in 1971. Because minocycline,like doxycycline, lacks the 6-hydroxyl group, it is stablein acids and does not dehydrate or rearrange to anhydroor lactone forms. Minocycline is well absorbed orally togive high plasma and tissue levels. It has a very long serumhalf-life, resulting from slow urinary excretion and moderateprotein binding. Doxycycline and minocycline, alongwith oxytetracycline, show the least in vitro calcium bindingof the clinically available tetracyclines. The improved distributionproperties of the 6-deoxytetracyclines have been attributedto greater lipid solubility.Perhaps the most outstanding property of minocyclineis its activity toward Gram-positive bacteria, especiallystaphylococci and streptococci. In fact, minocycline hasbeen effective against staphylococcal strains that are resistantto methicillin and all other tetracyclines, includingdoxycycline. Although it is doubtful that minocyclinewill replace bactericidal agents for the treatment of lifethreateningstaphylococcal infections, it may become auseful alternative for the treatment of less serious tissueinfections. Minocycline has been recommended for thetreatment of chronic bronchitis and other upper respiratorytract infections. Despite its relatively low renal clearance,partially compensated for by high serum and tissuelevels, it has been recommended for the treatment of urinary tract infections. It has been effective in the eradicationof N. meningitidis in asymptomatic carriers.; View all

3.2 Usage: Second generation tetracycline antibiotic. Antibacterial.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S36

4.1 Packing Group: III

4.1 Hazard Class: 6.1(b)

4.1 Hazard Declaration: H315

4.1 RIDADR: 3249

4.1 Caution Statement: P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: QI7630500

4.1 Safety: Hazard Codes:?Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
RIDADR: 3249
WGK Germany: 3
RTECS: QI7630500
HazardClass: 6.1(b)
PackingGroup：? III
Risk Statements：?Irritating to the eyes；Irritating to the respiratory system；Irritating to the skin
Safety Statements：?Wear suitable protective clothing
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and parenteral routes. Human systemic effects: dermatitis, eye effects, increased body temperature. When heated to decomposition it emits toxic fumes of NO_x and HCl.; View all

4.2 Specification: ?Minocycline hydrochloride , its cas register number is 13614-98-7. It also can be called Arestin ; Minocin ; Tri-minocycline ; and [4S-(4alpha,4aalpha,5aalpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxonaphthacene-2-carboxamide monohydrochloride .

4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
human	TDLo	oral	14286ug/kg/10 (14.286mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION LUNGS, THORAX, OR RESPIRATION: DYSPNEA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Archives of Internal Medicine. Vol. 154, Pg. 1633, 1994.
man	TDLo	intravenous	2857ug/kg (2.857mg/kg)	LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Internal Medicine. Vol. 33, Pg. 177, 1994.
man	TDLo	oral	11429ug/kg/4D (11.429mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Archives of Dermatology. Vol. 123, Pg. 18, 1987.
man	TDLo	oral	3893mg/kg/4Y- (3893mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Archives of Dermatology. Vol. 122, Pg. 17, 1986.
mouse	LD50	intraperitoneal	299mg/kg (299mg/kg)	?	Drugs in Japan Vol. 6, Pg. 811, 1982.
mouse	LD50	intravenous	154mg/kg (154mg/kg)	?	Drugs in Japan Vol. 6, Pg. 811, 1982.
mouse	LD50	oral	3600mg/kg (3600mg/kg)	?	Drugs in Japan Vol. 6, Pg. 811, 1982.
mouse	LD50	subcutaneous	2290mg/kg (2290mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 21, Pg. 319, 1990.
mouse	LDLo	parenteral	620mg/kg (620mg/kg)	?	Chemotherapy Vol. 24, Pg. 17, 1978.
rat	LD50	intraperitoneal	331mg/kg (331mg/kg)	?	Drugs in Japan Vol. 6, Pg. 811, 1982.
rat	LD50	intravenous	164mg/kg (164mg/kg)	?	Drugs in Japan Vol. 6, Pg. 811, 1982.
rat	LD50	oral	2380mg/kg (2380mg/kg)	?	Drugs in Japan Vol. 6, Pg. 811, 1982.
rat	LD50	subcutaneous	1700mg/kg (1700mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 21, Pg. 319, 1990.
women	TDLo	oral	42mg/kg/3W-I (42mg/kg)	BLOOD: AGRANULOCYTOSIS BLOOD: OTHER CHANGES MUSCULOSKELETAL: JOINTS	Archives of Internal Medicine. Vol. 154, Pg. 1983, 1994.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Other Information

6.0 Collision Cross Section: 208.1 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

6.1 Mesh: Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

6.2 Mesh Entry Terms: Akamin

6.3 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

6.4 Merck: 14,6202

6.5 Chemical Properties: Yellow Crystalline Powder

6.6 Uses: antiinflammatory

6.7 Uses: Minocycline hydrochloride is a salt prepared from minocycline, taking advantage of the two basic dimethylamino groups which protonate and readily form a salt from hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Like all tetracyclines, minocycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis.

6.8 Uses: Second generation tetracycline antibiotic. Antibacterial.

6.9 Brand name: Dynacin (Medicis); Minocin (Lederle); Minocin (Triax); Solodyn (Medicis).

6.10 Originator: Minocin,Lederle ,US,1971

6.11 Manufacturing Process: Preparation of 7-(N,N'-Dicarbobenzyloxyhydrazino)-6-Demethyltetracycline: A1.0 g portion of 6-demethyltetracycline was dissolved in a mixture of 9.6 ml oftetrahydrofuran and 10.4 ml of methanesulfonic acid at -10°C. The mixturewas allowed to warm to 0°C. A solution of 0.86 g of dibenzyl azodicarboxylatein 0.5 ml of tetrahydrofuran was added dropwise and the mixture was stirredfor 2 hours while the temperature was maintained at 0°C. The reactionmixture was added to ether. The product was filtered off, washed with etherand then dried. The 7-(N,N'-dicarbobenzyloxyhydrazino)-6-demethyltetracycline was identified by paper chromatography.
Reductive Methylation of 7-(N,N'-Dicarbobenzyloxyhydrazino)-6-Demethyl-6-Deoxytetracycline to 7-Dimethylamino-6-Demethyl-6-Deoxytetracycline: Asolution of 100 mg of 7(N,N'-dicarbobenzyloxyhydrazino)-6-demethyl-6-deoxytetracycline in 2.6 ml of methanol, 0.4 ml of 40% aqueous ormaldehyde solution and 50 mg of 5% palladium on carbon catalyst washydrogenated at room temperature and two atmospheres pressure. Uptake ofthe hydrogen was complete in 3 hours. The catalyst was filtered off and thesolution was taken to dryness under reduced pressure. The residue wastriturated with ether and then identified as 7-dimethylamino-6-demethyl-6-deoxytetracycline by comparison with an authentic sample, according to USPatent 3,483,251.; View all

6.12 Therapeutic Function: Antibiotic

6.13 General Description: Minocycline, 7-dimethylamino-6-demethyl-6-deoxytetracycline(Minocin, Vectrin), the most potent tetracycline currentlyused in therapy, is obtained by reductive methylationof 7-nitro-6-demethyl-6-deoxytetracycline. It was releasedfor use in the United States in 1971. Because minocycline,like doxycycline, lacks the 6-hydroxyl group, it is stablein acids and does not dehydrate or rearrange to anhydroor lactone forms. Minocycline is well absorbed orally togive high plasma and tissue levels. It has a very long serumhalf-life, resulting from slow urinary excretion and moderateprotein binding. Doxycycline and minocycline, alongwith oxytetracycline, show the least in vitro calcium bindingof the clinically available tetracyclines. The improved distributionproperties of the 6-deoxytetracyclines have been attributedto greater lipid solubility.
Perhaps the most outstanding property of minocyclineis its activity toward Gram-positive bacteria, especiallystaphylococci and streptococci. In fact, minocycline hasbeen effective against staphylococcal strains that are resistantto methicillin and all other tetracyclines, includingdoxycycline. Although it is doubtful that minocyclinewill replace bactericidal agents for the treatment of lifethreateningstaphylococcal infections, it may become auseful alternative for the treatment of less serious tissueinfections. Minocycline has been recommended for thetreatment of chronic bronchitis and other upper respiratorytract infections. Despite its relatively low renal clearance,partially compensated for by high serum and tissuelevels, it has been recommended for the treatment of urinary tract infections. It has been effective in the eradicationof N. meningitidis in asymptomatic carriers.; View all

6.14 Biochem/physiol Actions: Minocycline is a broad spectrum antibiotic with bacteriostatic function. Minocycline has anti-inflammatory properties. Minocycline inhibits lipopolysaccharide mediated inflammatory cytokine tumour necrosis factor (TNF-α) secretion by macrophages. Minocycline inhibits macrophage proliferation in a dose dependent manner. Minocycline inhibits neuroinflammation in pre-plaque of Alzheimer′s disease-like amyloid pathology through inhibition of key inflammatory enzymes like inducible nitric oxide synthase (iNOS), matrix metalloproteinase 9 (MMP-9) and 5-lipoxygenase. Minocycline inhibits endothelial cell proliferation and angiogenesis. Minocycline exhibits anti-tumor activity in glioma by inhibiting membrane type 1 matrix metalloproteinase (MT1-MMP). Minocycline increases cognition and neuronal differentiation. zMinocycline effectively reduces neuropathic pain by increasing the functions of nociceptin/orphanin FQ.

6.15 Veterinary Drugs and Treatments: Minocycline may be useful for treating Brucellosis (in combination with aminoglycosides), Lyme disease, and certain nosocomial infections where other more commonly used drugs are ineffective. It has been investigated as adjunctive therapy for treating hemangiosarcomas, but early results have been disappointing.

6.16 Usage: The primary aim of this material is for research purpose only.

6.17 Usage: A broad spectrum antibiotic commonly used against bacteria which cause upper respiratory tract infections

7. Computational chemical data

Molecular Weight: 493.941g/mol
Molecular Formula: C₂₃H₂₈ClN₃O₇
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 493.1615779
Monoisotopic Mass: 493.1615779
Complexity: 971
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 6
Hydrogen Bond Acceptor Count: 9
Topological Polar Surface Area: 165
Heavy Atom Count: 34
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7OAAEAAAAAAAAAAAAAAAAAAAAAAAwYIEAAAAAAACBAAAAHgAQCAAADWzBmAQyxoNAAgCIAqVSUAKCAAAhIgAIiAHObMgJJz7KkLOEcAhn4BFJ2Qe+zvCugEABQAAaAADAgAaAADQAAAAAAAAAAA==

8. Question & Answer

What is the pharmacological action of Minocycline hydrochloride? Jun 29 2022
Minocycline hydrochloride is a widely used antibiotic in medicine. It not only acts as a bactericidal and bacteriostatic agent, but also improves symptoms such as diarrhea, dizziness, and nausea in pa..
What are the side effects of Minocycline hydrochloride? Nov 09 2020
Like many other medications, Minocycline hydrochloride also has some side effects when used in daily life. Minocycline hydrochloride gel is commonly used to treat conditions such as enteritis, cholecy..
What is the mechanism of action and uses of Minocycline hydrochloride? Oct 24 2020
Overview[1-2] Minocycline hydrochloride is a yellow crystalline powder that is soluble in water, slightly soluble in ethanol, and easily soluble in alkaline metal hydroxide or carbonate solutions. Its..

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