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111470-99-6

Basic Information
CAS No.: 111470-99-6
Name: Amlodipine besylate
Article Data: 20
Molecular Structure:
Molecular Structure of 111470-99-6 (Amlodipine besylate)
Formula: C20H25ClN2O5.C6H6O3S
Molecular Weight: 567.06
Synonyms: Amlodipine benzenesulfonate;Monopina;Amlodin;Norvas;3,5-Pyridinedicarboxylic acid,2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)- 1,4-dihydro-6-methyl-,3-ethyl 5-methyl ester,monobenzenesulfonate;3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl-5-methyl ester, monobenzenesulfonate;Myodura;Amcard;Tensivask;Norvasc (TN);3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (+-)-, monobenzenesulfonate;Amdipin;Amlogard;Norvask;Antacal;3-Ethyl 5-methyl (+-)-2-((2-aminoethoxy)methyl)-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate, monobenzenesulfonate;Terloc;Astudar;benzenesulfonic acid; ethyl methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;Norvasc;Cordarene;Cardiorex;
EINECS: 1312995-182-4
Density: 1.227 g/cm3
Melting Point: 199-201 ºC
Boiling Point: 527.2 ºC at 760 mmHg
Flash Point: 272.6 ºC
Solubility: Slightly soluble in water; sparingly soluble in ethanol
Appearance: White powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38-20/21/22
Safety: 26-36
PSA: 162.63000
LogP: 5.30950
Synthetic route
88150-62-3

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine

98-11-3

benzenesulfonic acid

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
Stage #1: 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine With methylamine at 25℃; Large scale;
Stage #2: benzenesulfonic acid In water at 30℃; Temperature; Large scale;
91.6%
Stage #1: 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine With methylamine In water at 20 - 45℃; for 4.5h;
Stage #2: benzenesulfonic acid In water at 20℃; for 4.5h; pH=1 - 2; Product distribution / selectivity;
Stage #1: 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine With hydrazine In methanol; ethyl acetate at 34 - 37℃; for 0.05h; Inert atmosphere;
Stage #2: benzenesulfonic acid In isopropyl alcohol at 5 - 30℃; for 2h;
Stage #1: 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine With methylamine In dichloromethane at 25℃; for 4h;
Stage #2: benzenesulfonic acid In dichloromethane at 25℃;
48 g
246852-08-4

amlodipine formate

515-42-4

sodium phenylsulfonate

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
In water at 5 - 20℃; for 0.333333h; Product distribution / selectivity;90%
246852-11-9

amlodipine chloroacetate

515-42-4

sodium phenylsulfonate

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
Product distribution / selectivity;89%

amlodipine Hydrochloride

515-42-4

sodium phenylsulfonate

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
In water at 10 - 20℃; for 0.833333h; Product distribution / selectivity;88%
88150-42-9

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

98-11-3

benzenesulfonic acid

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
In methanol; toluene at 0 - 20℃; for 2h;87%
for 3h;
In isopropyl alcohol at 0 - 30℃; for 2 - 2.25h; Product distribution / selectivity;
246852-10-8

amlodipine acetate

515-42-4

sodium phenylsulfonate

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
In ethanol; water at 5 - 20℃; for 0.5h; Product distribution / selectivity;83%
246852-13-1

amlodipine nitrate

515-42-4

sodium phenylsulfonate

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
Product distribution / selectivity;83%

amlodipine mesylate

515-42-4

sodium phenylsulfonate

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
Product distribution / selectivity;81%
156366-27-7

N-tritylamlodipine

98-11-3

benzenesulfonic acid

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
With ethanol for 4.66667h; Heating / reflux;
With methanol at 45℃; Kinetics; Reagent/catalyst; Temperature; Large scale reaction;
156366-27-7

N-tritylamlodipine

98-11-3

benzenesulfonic acid

A

331258-31-2

diethyl 2,6-bis[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate

B

140171-66-0

dimethyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

C

111470-99-6

amlodipine besylate

Conditions
ConditionsYield
In methanol for 2h; Heating / reflux;
In methanol for 2h; Heating / reflux;
Downstream Products
88150-42-9
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    Items Standard Result Assay (Ursolic acid) 98%min 98.22% -----------------------------------------------------------------------------------------------------------

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Specification

1.Introduction of Amlodipine besylate

The Amlodipine besylate, with its CAS NO.111470-99-6, is a kind of white powder. It has synonyms of  -Ethyl 5-methyl (+-)-2-((2-aminoethoxy)methyl)-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate, monobenzenesulfonate ; Amcard ; Amdepin ; Amdipin ; Amlodin ; Amlodipine benzenesulfonate ; Amlodipine besilate and ,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (+-)-, monobenzenesulfonate. Amlodipine besylate should be stored in shady and cool warehouse and mainly used as pharmaceutical Intermediates.


2.Properties of Amlodipine besylate

(1) Melting Point: 199-201 °C  (2) solubility: DMSO: 20 mg/mL  (3) Flash Point: 272.6 °C
(4) Enthalpy of Vaporization: 80.17 kJ/mol  (5) Boiling Point: 527.2 °C at 760 mmHg
(6) Vapour Pressure of Amlodipine besylate:3.34E-11 mmHg at 25 °C

3.Structure descriptors of Amlodipine besylate

IUPAC Name: benzenesulfonic acid; 3-O-ethyl 5-O-methyl
2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,
4-dihydropyridine-3,5-dicarboxylate

InChI: InChI=1S/C20H25ClN2O5.C6H6O3S/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)
16(19(24)26-3)17(18)13-7-5-6-8-14(13)21;7-10(8,9)6-4-2-1-3-5-6/h5-8,17,
23H,4,9-11,22H2,1-3H3;1-5H,(H,7,8,9)

InChIKey: ZPBWCRDSRKPIDG-UHFFFAOYSA-N

Canonical SMILES : CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN.C1=CC=C(C=C1)S(=O)(=
O)O
 

4.Safety data of Amlodipine besylate

Hazard Codes:HarmfulXn
Risk Statements: 22-36/37/38-20/21/22
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
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.
WGK Germany: 3
RTECS of Amlodipine besylate (CAS NO.111470-99-6): US7967700
 

5.Toxity data of Amlodipine besylate

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 10mg/kg (10mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 36, Pg. 1169, 1994.
man TDLo oral 1429ug/kg (1.429mg/kg) VASCULAR: SHOCK

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
American Journal of Emergency Medicine. Vol. 16, Pg. 527, 1998.
mouse LD50 intraperitoneal 31mg/kg (31mg/kg)   Drugs in Japan Vol. -, Pg. 71, 1995.
mouse LD50 oral 37mg/kg (37mg/kg)   Drugs in Japan Vol. -, Pg. 71, 1995.
mouse LD50 subcutaneous 36mg/kg (36mg/kg)   Drugs in Japan Vol. -, Pg. 71, 1995.
rat LD50 intraperitoneal 42mg/kg (42mg/kg)   Drugs in Japan Vol. -, Pg. 71, 1995.
rat LD50 oral 393mg/kg (393mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BLOOD: OTHER CHANGES
Oyo Yakuri. Pharmacometrics. Vol. 42, Pg. 177, 1991.
rat LD50 subcutaneous 678mg/kg (678mg/kg)   Drugs in Japan Vol. -, Pg. 71, 1995.
women TDLo oral 1mg/kg (1mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Annals of Pharmacotherpy. Vol. 31, Pg. 853, 1997.
women TDLo unreported 6mg/kg/60D-I (6mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Lancet. Vol. 341, Pg. 1102, 1993.