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| CAS No.: | 88150-42-9 |
|---|---|
| Name: | Amlodipine |
| Article Data: | 24 |
| Molecular Structure: | |
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| 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 |
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- 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 |
- 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
| 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 | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 16 h 2: H2 / 5percent Pd/CaCO3 / ethanol / 1 h / Ambient temperature View Scheme |
- 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
| Conditions | Yield |
|---|---|
| With ammonium formate; palladium dihydroxide In methanol; dichloromethane |
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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 %.
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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. |