CAS No.88150-42-9,Amlodipine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	88150-42-9
Name:	Amlodipine
Article Data:	24

Formula:	C₂₀H₂₅ClN₂O₅
Molecular Weight:	408.882
Synonyms:	(R,S)-Amlodipine;Amlopres;Intervask;Racemic Amlodipine;Amlodipine base;Amlodipine(base);Amlodipine;
EINECS:	1308068-626-2
Density:	1.227 g/cm³
Melting Point:	178-179 °C
Boiling Point:	527.2 °C at 760 mmHg
Flash Point:	272.6 °C
Solubility:	75.3 mg/L in water
Appearance:	Yellow solid
PSA:	99.88000
LogP:	3.29540

Synthetic route

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
With sodium cyanoborohydride; acetic acid at 15 - 25℃; for 2h; Reagent/catalyst; Temperature;	93.1%

: 111470-99-6
amlodipine besylate

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
With sodium hydroxide In water for 0.5h; Heating / reflux;	88.6%
With sodium hydroxide In tert-butyl methyl ether; water
With sodium hydroxide In methanol; water
With sodium hydroxide In water for 1h; Reagent/catalyst; Reflux;

: 88150-62-3
4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
With ethanol; methylamine at 28 - 32℃; for 17h;	87.2%
With hydrazine In methanol; toluene at 22 - 24℃; for 7h;	86.5%
With methylamine In ethanol for 3h; Ambient temperature;

: 88150-46-3
2-(2-azidoethoxy)methyl-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
With hydrogen; Lindlar's catalyst In ethanol for 1h; Ambient temperature;
With hydrogen; 5% Pd/CaCO3 In ethanol under 775.743 Torr;

: 638-07-3
ethyl (2-chloroaceto)acetate

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) THF, 1 h, 2.) THF, RT, overnight 2: 25 percent / propan-2-ol / 21 h / Heating 3: methylamine / ethanol / 3 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, RT, 16 h 2: NH4OAc / ethanol / 1 h / Heating 3: ethanol / 5 h / Heating 4: 16 h 5: H2 / 5percent Pd/CaCO3 / ethanol / 1 h / Ambient temperature View Scheme

: 88150-45-2
ethyl 4-(2-azidoethoxy)acetoacetate

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NH4OAc / ethanol / 1 h / Heating 2: ethanol / 5 h / Heating 3: 16 h 4: H2 / 5percent Pd/CaCO3 / ethanol / 1 h / Ambient temperature View Scheme

: 88150-75-8
ethyl 4-[2-(phthalimido)ethoxy]acetoacetate

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 25 percent / propan-2-ol / 21 h / Heating 2: methylamine / ethanol / 3 h / Ambient temperature View Scheme

: (E)-3-Amino-4-(2-azido-ethoxy)-but-2-enoic acid ethyl ester

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 5 h / Heating 2: 16 h 3: H2 / 5percent Pd/CaCO3 / ethanol / 1 h / Ambient temperature View Scheme

: 120289-15-8
2-(2-azidoethoxy)methyl-5-carboxy-4-(2-chlorophenyl)-3-ethoxycarbonyl-6-methyl-1,4-dihydropyridine

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 16 h 2: H2 / 5percent Pd/CaCO3 / ethanol / 1 h / Ambient temperature View Scheme

: 4-(2-chloro-phenyl)-2-(2-hydroxyimino-ethoxymethyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
With ammonium formate; palladium dihydroxide In methanol; dichloromethane

Raw Materials

638-07-3

Downstream Products

58-93-5

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History

Amlodipine is marketed as Dailyvasc in the Philippines by Xeno Pharmaceuticals, and by Pfizer as Norvasc in North America, Australia and some European countries, and as Istin in the United Kingdom. Generic brands are also available.

Specification

1.Introduction of Amlodipine

The Amlodipine,with its cas number 88150-42-9, is a kind of white solid.It is also called (1)3-Ethyl-5-methyl ( -)-2-((2-aminoethoxy)methyl)-4-(2-chlorphenyl)-1,4-dihydro-6-methyl-3,5-pyridindicarboxylat and (2)3-Ethyl-5-methyl ( -)-2-((2-aminoethoxymethyl)-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate. Amlodipine should be stored in shady and cool warehouse and mainly used as antagonist.

2.Properties of Amlodipine

(1)ACD/LogP: 4.16 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 1.23 ; (4)ACD/LogD (pH 7.4): 2.64 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 26.11 ; (7)ACD/KOC (pH 5.5): 5.14 ; (8)ACD/KOC (pH 7.4): 133.65 ; (9)#H bond acceptors: 7 ; (10)#H bond donors: 3 ; (11)#Freely Rotating Bonds: 11 ; (12)Polar Surface Area: 68.31 Å²; (13)Index of Refraction: 1.545 ; (14)Molar Refractivity: 105.41 cm³ ; (15)Molar Volume: 333 cm³ ; (16)Polarizability: 41.79 ×10^-24cm³ ; (17)Surface Tension: 44.4 dyne/cm ; (18)Density: 1.227 g/cm³ ; (19)Flash Point: 272.6 °C ; (20)Enthalpy of Vaporization: 80.17 kJ/mol ; (21)Boiling Point: 527.2 °C at 760 mmHg ; (22)Vapour Pressure: 3.34E-11 mmHg at 25°C

3.Structure descriptors of Amlodipine

IUPAC Name: 3-O-ethyl 5-O-methyl

2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,
4-dihydropyridine-3,5-dicarboxylate

InChI: InChI=1S/C20H25ClN2O5/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/h5-8,17,23H,4,9-11,22H2,1-3H3

InChIKey: HTIQEAQVCYTUBX-UHFFFAOYSA-N

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

4. Uses of Amlodipine

The Amlodipine is used as an anti-hypertensive and in the treatment of angina because it is a long-acting calcium channel blocker. Seemimg Like other calcium channel blockers, Amlodipine reduce blood pressure by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance. Besides, it increases blood flow to the heart muscle in angina. Adverse effcts include common headache, fatigue, insomnia, edema, abdominal pain, nausea, dizziness, palpitation and red face. Rare rash, itching, expiratory dyspnea, muscle spasm and indigestion. Rarely have myocardial infarction and chest. It can have edema, headache, dizziness, weakness, etc.

5.Production of Amlodipine

The Amlodipine can react with nicotinic acid to obtain 4-(2-chloro-phenyl)-2-methyl-6-{2-[(pyridine-3-carbonyl)-amino]-ethoxymethyl}-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-ethyl ester 3-methyl ester.
Reaction condition is CH2Cl2 as solvent under ambient temperature for 16 hour(s). Yield is 57 %.

6. The toxity data can be showed in the following sheet.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	400ug/kg (0.4mg/kg)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	American Journal of Emergency Medicine. Vol. 18, Pg. 581, 2000.
women	LDLo	oral	1400ug/kg (1.4mg/kg)	CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 253, 1995.
women	TDLo	oral	600ug/kg/3D-I (0.6mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BLOOD: HEMORRHAGE BLOOD: THROMBOCYTOPENIA	Annals of Pharmacotherpy. Vol. 33, Pg. 1126, 1999.