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CAS

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Amlodipine is a dihydropyridine L-type calcium channel blocker that selectively inhibits calcium influx in cardiac and vascular smooth muscle. It acts as a vasodilator, reducing blood pressure by relaxing the smooth muscle in the arterial wall and decreasing total peripheral resistance. Amlodipine also exhibits actions independent of L-type calcium channel blockade, such as regulating membrane fluidity and cholesterol deposition, stimulating nitric oxide production, acting as an antioxidant, and regulating matrix deposition in vitro and in vivo.

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  • 3,5-Pyridinedicarboxylicacid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-,3-ethyl 5-methyl ester/ LIDE PHARMA- Factory supply / Best price

    Cas No: 88150-42-9

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  • 88150-42-9 Structure

  • Basic information

    1. Product Name: Amlodipine
    2. Synonyms: 3,5-pyridinedicarboxylicacid,1,4-dihydro-2-((2-aminoethoxy)methyl)-4-(2-chlor;3-ethyl5-methylester;LOTREL;methyl ethyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;AMLODIPINE;AMLODIPINE BASE;Amlodipin;besylate
    3. CAS NO:88150-42-9
    4. Molecular Formula: C20H25ClN2O5
    5. Molecular Weight: 567.05
    6. EINECS: 1308068-626-2
    7. Product Categories: Active Pharmaceutical Ingredients;Dihydropyridine Class Chemicals;Intermediates & Fine Chemicals;Pharmaceuticals;Calcium channel;Aromatics;Dihydropyridine;Heterocycles;API;Free Base API;Norvasc
    8. Mol File: 88150-42-9.mol

  • Chemical Properties

    1. Melting Point: 178-179°C
    2. Boiling Point: 527.2 °C at 760 mmHg
    3. Flash Point: 272.6 °C
    4. Appearance: Yellow solid
    5. Density: 1.227 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: -20°C Freezer
    8. Solubility: Soluble in DMSO (up to 25 mg/ml), in DMF (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
    9. PKA: pKa 8.6 (Uncertain)
    10. Water Solubility: 75.3 mg/L
    11. Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO, DMF, or ethanol may be stored at -20°C for up to 3 months.
    12. CAS DataBase Reference: Amlodipine(CAS DataBase Reference)
    13. NIST Chemistry Reference: Amlodipine(88150-42-9)
    14. EPA Substance Registry System: Amlodipine(88150-42-9)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS: US7968329
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 88150-42-9(Hazardous Substances Data)

88150-42-9 Usage

Uses

Used in Pharmaceutical Industry:
Amlodipine is used as an anti-hypertensive and calcium channel blocker for the treatment of hypertension. It helps to lower blood pressure by relaxing the smooth muscle in the arterial wall and decreasing total peripheral resistance.
Used in Research and Development:
Amlodipine is used as a deuterated dihydropyridine calcium channel blocker in the development of labeled APIs. Labeled Amlodipine serves as an internal standard for the quantification of Amlodipine by GCor LC-mass spectrometry, aiding in research and quality control processes.

Hazard

Human systemic effects.

Clinical Use

Calcium-channel blocker: Hypertension Angina prophylaxis

Safety Profile

Human systemic effects. Whenheated to decomposition it emits toxic vapors of NOx andCl-.

Drug interactions

Potentially hazardous interactions with other drugs Aminophylline and theophylline: possibly increased aminophylline and theophylline concentration. Anaesthetics: enhanced hypotensive effect. Antibacterials: metabolism possibly inhibited by clarithromycin, erythromycin and telithromycin. Antidepressants: enhanced hypotensive effect with MAOIs, concentration possibly reduced by St John’s wort. Antiepileptics: effects probably reduced by phenobarbital and primidone. Antifungals: negative inotropic effect possibly increased with itraconazole. Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect of postsynaptic alpha-blockers. Antivirals: concentration increased by telaprevir and possibly by ritonavir - reduce dose of amlodipine. Ciclosporin: ciclosporin concentration may be increased by up to 40%. Lipid lowering agents: possibly increased risk of myopathy - do not exceed 20 mg of simvastatin.1 Tacrolimus: possibly increased tacrolimus levels.

Metabolism

Amlodipine is extensively metabolised by the liver to inactive metabolites with 10% of the parent compound and 60% of metabolites excreted in the urine.

References

1) Mason et al. (2003), Novel vascular biology of third-generation L-type calcium channel antagonists: ancillary actions of amlodipine; Arterioscler. Thromb. Vasc. Biol., 23 2155 2) Asano et al. (2003), A calcium channel blocker activates both ecto-5(‘)-nucleotidase and NO synthase in HUVEC; Biochem. Biophys. Res. Commun., 311 625 3) Yu et al. (2003), Amlodipine modulates THP-1 cell adhesion to vascular endothelium via inhibition of protein kinase C signal transduction; Hypertension, 42 329 4) Zhou et al. (2004), Inhibition of oxidative stress and improvement of endothelial function by amlodipine in angiotensin II-infused rats; Am. J. Hypertension, 17 167 5) Ueda et al. (1993), A comparative assessment of the duration of action of amlodipine and nifedipine GITS in normotensive subjects; Br. J. Clin. Pharmacol., 36 561

Check Digit Verification of cas no

The CAS Registry Mumber 88150-42-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,8,1,5 and 0 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 88150-42:
(7*8)+(6*8)+(5*1)+(4*5)+(3*0)+(2*4)+(1*2)=139
139 % 10 = 9
So 88150-42-9 is a valid CAS Registry Number.
InChI:InChI=1/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

88150-42-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name amlodipine

1.2 Other means of identification

Product number -
Other names Norvasc

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:88150-42-9 SDS

88150-42-9Synthetic route

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

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

2-[(2-aminoethoxy)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
ConditionsYield
With sodium cyanoborohydride; acetic acid at 15 - 25℃; for 2h; Reagent/catalyst; Temperature;93.1%
amlodipine besylate
111470-99-6

amlodipine besylate

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

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

2-[(2-aminoethoxy)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
ConditionsYield
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;
2-(2-azidoethoxy)methyl-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
88150-46-3

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

2-[(2-aminoethoxy)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
ConditionsYield
With hydrogen; Lindlar's catalyst In ethanol for 1h; Ambient temperature;
With hydrogen; 5% Pd/CaCO3 In ethanol under 775.743 Torr;
ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

2-[(2-aminoethoxy)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
ConditionsYield
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
ethyl 4-(2-azidoethoxy)acetoacetate
88150-45-2

ethyl 4-(2-azidoethoxy)acetoacetate

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

ethyl 4-[2-(phthalimido)ethoxy]acetoacetate

2-[(2-aminoethoxy)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
ConditionsYield
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

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

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

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

2-[(2-aminoethoxy)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
ConditionsYield
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

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

2-[(2-aminoethoxy)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
ConditionsYield
With ammonium formate; palladium dihydroxide In methanol; dichloromethane
(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester
103129-81-3

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

2-[(2-aminoethoxy)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
ConditionsYield
Multi-step reaction with 2 steps
1: calcium hypochlorite / ethyl acetate; water / 20 - 30 °C
2: acetic acid; sodium cyanoborohydride / 2 h / 15 - 25 °C
View Scheme
2-[(2-aminoethoxy)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

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

amlodipine (R)-(+)-pyroglutamate
663180-17-4

amlodipine (R)-(+)-pyroglutamate

Conditions
ConditionsYield
In ethanol at 5 - 20℃; for 1h;97.1%
malonic acid
141-82-2

malonic acid

2-[(2-aminoethoxy)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

amlodipine malonate salt
851447-21-7

amlodipine malonate salt

Conditions
ConditionsYield
In ethanol at 5 - 20℃; for 1h;96.8%
Hippuric Acid
495-69-2

Hippuric Acid

2-[(2-aminoethoxy)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

amlodipine hipurate salt
851447-18-2

amlodipine hipurate salt

Conditions
ConditionsYield
In ethanol at 5 - 20℃; for 1h;96.8%
L-Tartaric acid
87-69-4

L-Tartaric acid

2-[(2-aminoethoxy)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

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

(S)-amlodipine-L-hemitartrate dimethylformamide solvate

(S)-amlodipine-L-hemitartrate dimethylformamide solvate

B

(R)-amlodipine-L-hemitartrate dimethylformamide solvate

(R)-amlodipine-L-hemitartrate dimethylformamide solvate

C

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester
103129-81-3

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

Conditions
ConditionsYield
at 20℃; for 4.5h; Product distribution / selectivity;A 96.25%
B n/a
C n/a
methanesulfonic acid
75-75-2

methanesulfonic acid

2-[(2-aminoethoxy)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

amlodipine mesylate

amlodipine mesylate

Conditions
ConditionsYield
In water; ethyl acetate at 25℃; Temperature; Solvent;96%
In methanol; toluene at 0 - 5℃; for 15h;90%
In ethyl acetate at 20℃; for 1h;3.32%
In ethyl acetate at 0 - 25℃; for 2 - 2.25h; Product distribution / selectivity;
(S)-Malic acid
97-67-6

(S)-Malic acid

2-[(2-aminoethoxy)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

amlodipine hemi-L-malate salt

amlodipine hemi-L-malate salt

Conditions
ConditionsYield
In ethanol at 5 - 20℃; for 1h;96%
2-[(2-aminoethoxy)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

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

amlodipine (S)-(-)-pyroglutamate
663180-18-5

amlodipine (S)-(-)-pyroglutamate

Conditions
ConditionsYield
In ethyl acetate at 25℃; for 1h;95.3%
2-methylglutaric acid
18069-17-5

2-methylglutaric acid

2-[(2-aminoethoxy)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

amlodipine hemi-2-methyl glutarate salt

amlodipine hemi-2-methyl glutarate salt

Conditions
ConditionsYield
In diethyl ether; tert-butyl alcohol at 5 - 20℃; for 4h;95%
2-[(2-aminoethoxy)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

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

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

Conditions
ConditionsYield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h; Solvent;95%
2-[(2-aminoethoxy)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

dimethyl N-cyanodithioiminocarbonate
10191-60-3

dimethyl N-cyanodithioiminocarbonate

N-<2-<<4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyrid-2-yl>methoxy>ethyl>-N'-cyano-S-methylisothiourea
93117-86-3

N-<2-<<4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyrid-2-yl>methoxy>ethyl>-N'-cyano-S-methylisothiourea

Conditions
ConditionsYield
In isopropyl alcohol for 4h; Ambient temperature;94%
2-[(2-aminoethoxy)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

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.25h;94%
2-[(2-aminoethoxy)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

acetic acid
64-19-7

acetic acid

2-(2-aminoethoxy)methyl-3-ethoxycarbonyl-4-(o-chlorophenyl)-5-methoxycarbonyl-6-methylpyridine acetate

2-(2-aminoethoxy)methyl-3-ethoxycarbonyl-4-(o-chlorophenyl)-5-methoxycarbonyl-6-methylpyridine acetate

Conditions
ConditionsYield
With lead(IV) acetate In dichloromethane at 20℃; for 0.75h;92%
4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

2-[(2-aminoethoxy)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

amlodipine p-hydroxyphenylacetate
652969-06-7

amlodipine p-hydroxyphenylacetate

Conditions
ConditionsYield
In ethyl acetate at 23℃; for 3h;92%
In ethyl acetate at 23℃; for 3h;92%
2-[(2-aminoethoxy)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

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

C32H34ClN2O6P

C32H34ClN2O6P

Conditions
ConditionsYield
With tert.-butylhydroperoxide; zinc(II) iodide In hexane; dichloromethane at 25℃; for 1h;92%
2-[(2-aminoethoxy)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

maleic acid
110-16-7

maleic acid

(RS)-amlodipine maleate
88150-47-4

(RS)-amlodipine maleate

Conditions
ConditionsYield
In methanol; toluene at 21 - 24℃; for 1h;91.2%
In methanol; isopropyl alcohol at 25 - 30℃; for 1.5 - 1.75h; Product distribution / selectivity;
In methanol at 50℃;
3,5-dimethylbenzenesulfinic acid
18023-22-8

3,5-dimethylbenzenesulfinic acid

2-[(2-aminoethoxy)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

amlodipine meta-xylenesulfonate salt

amlodipine meta-xylenesulfonate salt

Conditions
ConditionsYield
In ethanol at 5 - 20℃; for 1h;91.1%
Adipic acid
124-04-9

Adipic acid

2-[(2-aminoethoxy)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

amlodipine adipate
526216-43-3

amlodipine adipate

Conditions
ConditionsYield
In methanol at 7 - 23℃; for 3h;91%
In methanol at 7 - 23℃; for 3h;91%
In methanol at 50℃;
2-[(2-aminoethoxy)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

amlodipine
103129-82-4

amlodipine

Conditions
ConditionsYield
Stage #1: 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With D-(+)-camphoric acid In isopropyl alcohol at 20℃; for 12.5h;
Stage #2: With sodium hydroxide In dichloromethane; water for 1h; Reagent/catalyst;		90.5%
With D-tartaric acid In dimethyl sulfoxide; acetone at 20 - 60℃; for 1.5h; Reagent/catalyst; Solvent;45.2%
Stage #1: 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With L-Tartaric acid In ISOPROPYLAMIDE at 5℃; for 2h; Resolution of racemate;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.666667h;		n/a
Multi-step reaction with 2 steps
1: water; iso-butanol / 1 h / 50 °C
2: sodium hydroxide / dichloromethane; water / pH 9
View Scheme
ethanesulfonic acid
594-45-6

ethanesulfonic acid

2-[(2-aminoethoxy)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

amlodipine ethanesulfonate
652970-52-0

amlodipine ethanesulfonate

Conditions
ConditionsYield
In methanol at 23℃; for 2h;90%
(1R)-(-)-10-camphorsulfonic acid

(1R)-(-)-10-camphorsulfonic acid

2-[(2-aminoethoxy)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

amlodipine (1R)-(-)-10-camphorsulfonate

amlodipine (1R)-(-)-10-camphorsulfonate

Conditions
ConditionsYield
In methanol at 7 - 22℃; for 3h;90%
2-[(2-aminoethoxy)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

(1S)-(+)-10-camphorsulfonic acid

(1S)-(+)-10-camphorsulfonic acid

amlodipine (1S)-(+)-10-camphorsulfonate

amlodipine (1S)-(+)-10-camphorsulfonate

Conditions
ConditionsYield
In methanol at 7 - 23℃; for 3h;90%
2-[(2-aminoethoxy)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

benzonitrile
100-47-0

benzonitrile

3-ethyl5-methyl2-((2-(benzylamino)ethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

3-ethyl5-methyl2-((2-(benzylamino)ethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With borane-ammonia complex; C16H29Cl2CoN2P at 20℃; for 13h; Schlenk technique; Inert atmosphere; chemoselective reaction;88%
2-[(2-aminoethoxy)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

benzenesulfonic acid
98-11-3

benzenesulfonic acid

amlodipine besylate
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;
cyclohexylsulfamic acid
100-88-9

cyclohexylsulfamic acid

2-[(2-aminoethoxy)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

amlodipine cyclamate
745013-02-9

amlodipine cyclamate

Conditions
ConditionsYield
In ethanol; ethyl acetate at 20℃; for 4h;87%
In ethanol; isopropyl alcohol at 0℃; for 4h;86%
In methanol; acetonitrile at 20℃; for 4h;85%
In isopropyl alcohol at 0℃; for 4h;82%
camphor-10-sulfonic acid
76-26-6, 3144-16-9, 5872-08-2, 35963-20-3

camphor-10-sulfonic acid

2-[(2-aminoethoxy)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

amlodipine camsylate

amlodipine camsylate

Conditions
ConditionsYield
In methanol at 10℃; for 2h;86.8%
2-[(2-aminoethoxy)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

Glycine ethyl ester isocyanate
2949-22-6

Glycine ethyl ester isocyanate

1-<2-<<4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyrid-2-yl>methoxy>ethyl>-3-<(ethoxycarbonyl)methyl>urea
97290-23-8

1-<2-<<4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyrid-2-yl>methoxy>ethyl>-3-<(ethoxycarbonyl)methyl>urea

Conditions
ConditionsYield
In acetonitrile for 2.5h; Heating;86%
3-methyl glutaric acid
626-51-7

3-methyl glutaric acid

2-[(2-aminoethoxy)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

amlodipine hemi-3-methyl glutarate salt

amlodipine hemi-3-methyl glutarate salt

Conditions
ConditionsYield
In diethyl ether; tert-butyl alcohol at 5 - 20℃; for 4h;85.7%

88150-42-9Relevant articles and documents

Light-Induced Formation/Scission of C-N, C-O, and C-S Bonds Enables Switchable Stability/Degradability in Covalent Systems

Hai, Yu,Li, Ziyi,Lu, Hanwei,Ye, Hebo,You, Lei,Zou, Hanxun

supporting information, p. 20368 - 20376 (2021/12/03)

The manipulation of covalent bonds could be directed toward degradable, recyclable, and sustainable materials. However, there is an intrinsic conflict between properties of stability and degradability. Here we report light-controlled formation/scission of three types of covalent bonds (C-N, C-O, and C-S) through photoswitching between equilibrium and nonequilibrium states of dynamic covalent systems, achieving dual benefits of photoaddressable stability and cleavability. The photocyclization of dithienylethene fused aldehyde ring-chain tautomers turns on the reactivity, incorporating/releasing amines, alcohols, and thiols reversibly with high efficiency, respectively. Upon photocycloreversion the system is shifted to kinetically locked out-of-equilibrium form, enabling remarkable robustness of covalent assemblies. Reaction coupling allows remote and directional control of a diverse range of equilibria and further broadens the scope. Through locking and unlocking covalent linkages with light when needed, the utility is demonstrated with capture/release of bioactive molecules, modification of surfaces, and creation of polymers exhibiting tailored stability and degradability/recyclability. The versatile toolbox for photoswitchable dynamic covalent reactions to toggle matters on and off should be appealing to many endeavors.

Method for preparing levamlodipine

-

Paragraph 0057-0066, (2020/10/14)

The invention provides a method for preparing levamlodipine and belongs to the technical field of medicine synthesis. The method provided by the invention comprises the following steps: concentratingamlodipine resolution mother liquor to be dry, then mixing with an oxidizing agent and a first solvent, and carrying out an oxidation reaction to obtain 2-((2-aminoethoxy)methyl)-4-(2-chlorphenyl)-6-methyl-3,5-pyridine ethyl methyl diformate, wherein the oxidizing agent is an achiral reagent; mixing the 2-((2-aminoethoxy)methyl)-4-(2-chlorphenyl)-6-methyl-3,5-pyridine ethyl methyl diformate, a reducing agent and a second solvent, and carrying out a reduction reaction to obtain an amlodipine racemate; and mixing the amlodipine racemate, a resolution reagent and a third solvent, and carrying outresolution treatment to obtain levamlodipine. According to the method provided by the invention, the amlodipine in the amlodipine resolution mother liquor can be effectively recycled and converted into high-value levamlodipine.

Two validated stability-indicating chromatographic methods for the separation of two anti-hypertensive combinations in the presence of their degradation products or impurities

Samy Mostafa, Noha,AbdElHamid, Ghada,Elsayed Zaazaa, Hala,Mohamed Amer, Sawsan

, p. 2427 - 2439 (2019/07/16)

Two RP-HPLC methods were developed, optimized, and validated for the determination of two different anti-hypertensive combinations in the presence of their degradation products or impurities and in their pharmaceutical formulations. The first mixture is Ramipril (RAM) in combination with Amlodipine besylate (AML) [mixture I], while the second one is a combination of Ramipril (RAM), Atorvastatin (ATV), and Aspirin (ASP) [mixture II].The proposed combinations were successfully separated on X-bridge C18column (250 × 4.6?mm i.d, 5?μm p.s.), using a mobile phase of 0.05?M phosphate buffer-acetonitrile-THF (60:40:0.1% by volume) pH 2.5 and an isocratic mobile phase formed of acetonitrile-0.05?M phosphate buffer-THF (60:40:0.1% by volume) pH 2.5 for mixture (I) and (II) at a flow rate of 1?mL/min and 1.2?mL/min, respectively. The compromising components of the mixtures were detected at 218?nm. For the best separation of the mentioned components different parameters were examined and optimized. The two suggested methods were validated in compliance with the ICH guidelines and were successfully applied for the quantification of the cited components in presence of their obtained degradation products as well as in their commercial pharmaceutical formulations. For both methods the obtained results were statistically analyzed and compared to those of the official and reported methods; using Student’s t test and F test showing no significant difference with high accuracy and good precision.

THERAPY FOR COMPLICATIONS OF DIABETES

-

, (2009/07/02)

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.

ANTIHYPERTENSIVE THERAPY

-

, (2009/09/08)

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

RAMIPRIL-AMLODIPINE SALT

-

Page/Page column 33, (2008/12/06)

The present invention relates to a ramipril-amlodipine salt.

The effect of ion pairing on the skin permeation of amlodipine

Jiang, Yuxuan,Fang, Liang,Niu, Xicao,Ma, Rui,He, Zhonggui

experimental part, p. 356 - 360 (2009/04/04)

The purpose of the present study was to evaluate the effect of ion pairing on the skin permeation of amlodipine. Amlodipine base (AM) was first prepared from amlodipine besilate (AM-B), then amlodipine adipate (AM-A), amlodipine oxalate (AM-O) and amlodipine maleate (AM-M) were prepared using AM and the corresponding organic acids. Differential scanning calorimetry (DSC) thermogram studies demonstrated the formation of complexes between AM and the various acids. In vitro percutaneous absorption of AM and its complexes was evaluated through excised rat skin using 2-chamber diffusion cells. The results showed that AM had the greatest steady-state flux and lowest permeability coefficient of the five compounds from the El system (ethanol : isopropyl myristate (IPM) = 2:8), and its four complexes all exhibited a lower flux and higher permeability coefficient than AM.

AN IMPROVED PROCESS FOR THE PREPARATION OF AMLODIPINE BESYLATE

-

Page/Page column 4-5, (2010/11/28)

The present invention provides a process for the preparation of amlodipine, which comprises purging of methylamine gas under stirring in phthaloyl amlodipine in presence of an organic solvent selected from the group consisting of toluene and isopropyl alcohol.

PROCESS FOR PREPARING AMLODIPINE

-

Page/Page column 7, (2010/11/28)

A process for preparing phthalimidoamlodipine, which is useful as an intermediate for the preparation of amlodipine and its salts.

PROCESS FOR THE PREPARATION OF PURE AMLODIPINE

-

Page/Page column 7, (2008/06/13)

The present invention relates to an improved process for the preparation of pure Amlodipine via the effective purification of phthalimido Amlodipine (3-ethyl-5-methyl -2-[(2-phthalimido ethoxy) methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-dicarboxylate).

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