Amlodipine

C₂₀H₂₅ClN₂O₅CAS 88150-42-9408.88 g/mol

Open in Covalent MOL file

Alkene Aryl halide Ester Ether Primary amine Secondary amine

Properties

Molecular formula: C₂₀H₂₅ClN₂O₅
Molar mass: 408.88 g/mol
Exact mass: 408.1452 Da
Melting point: 178–180 °C
pKa: 9.26
logP: 2.27Crippen estimate
Polar surface area: 99.9 Å²
H-bond donors / acceptors: 2 / 7
Rotatable bonds: 8

Hazards

Danger

H301 Toxic if swallowedAcute toxicity, oral
H318 Causes serious eye damageSerious eye damage/eye irritation
H373 ** May causes damage to organs through prolonged or repeated exposureSpecific target organ toxicity, repeated exposure
H400 Very toxic to aquatic lifeHazardous to the aquatic environment, acute hazard
H410 Very toxic to aquatic life with long lasting effectsHazardous to the aquatic environment, long-term hazard

Harmonised EU classification (CLP Annex VI, index 607-565-00-8), via PubChem.

Precautionary statements

P260, P264, P264+P265, P270, P273, P280, P301+P316, P305+P354+P338, P317, P319, P321, P330, P391, P405, P501

Identifiers

CAS number

88150-42-9

SMILES

CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1c1ccccc1Cl

InChIKey

HTIQEAQVCYTUBX-UHFFFAOYSA-N

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

Characterization data

Calculated from the structure, in the form journals print them.

¹H NMR

Predicted ¹H NMR (400 MHz, CDCl₃) δ 7.31 (dd, J = 7.7, 1.6 Hz, 1H), 7.21 (m, J = 7.7, 1.6 Hz, 1H), 7.19 (m, J = 7.7, 1.6 Hz, 1H), 7.16 (m, J = 7.7, 1.6 Hz, 1H), 4.48 (s, 1H), 4.08 (q, J = 7.0 Hz, 2H), 4.07 (s, 2H), 3.69 (t, J = 7.0 Hz, 2H), 3.67 (s, 3H), 3.60 (br s, 1H), 3.01 (t, J = 7.0 Hz, 2H), 1.71 (s, 3H), 1.26 (t, J = 7.0 Hz, 3H), 1.20 (br s, 2H).

¹³C NMR

Predicted ¹³C NMR (101 MHz, CDCl₃) δ 166.6, 166.6, 153.6, 152.3, 148.7, 132.8, 128.6, 127.4, 126.9, 126.4, 106.0, 105.0, 76.5, 70.2, 61.2, 52.1, 42.7, 41.0, 17.2, 13.7.

[M + H]+

[M + H]+ Calcd for C20H26ClN2O5 409.1525

[M + Na]+

[M + Na]+ Calcd for C20H25ClN2NaO5 431.1344

[M − H]−

[M − H]− Calcd for C20H24ClN2O5 407.1379

Elemental analysis

Anal. Calcd for C20H25ClN2O5: C, 58.75; H, 6.16; N, 6.85.

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

13 names · show all

3,5-Pyridinedicarboxylic acid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester
Racemic amlodipine
Pelmec
2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridine
(R,S)-Amlodipine
Amlopres
Intervask
(±)-Amlodipine
Adipin
Sofvasc
Egiramlon
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester
3-O-Ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Work with Amlodipine

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

(-)-Amlodipine103129-82-4Defined stereoisomer Amlodipine besylate111470-99-6Salt Amlodipine maleate88150-47-4Salt

Similar compounds

Phthaloylamlodipine88150-62-376 % similar Felodipine72509-76-364 % similar Felodipine86189-69-764 % similar Clevidipine167221-71-849 % similar Nitrendipine39562-70-447 % similar Lacidipine103890-78-441 % similar Nisoldipine63675-72-941 % similar Nifedipine21829-25-441 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

PubChem CAS Common Chemistry NIST WebBook