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N149

Sigma-Aldrich

Nimodipine

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Synonym(s):
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester, Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate
Empirical Formula (Hill Notation):
C21H26N2O7
CAS Number:
66085-59-4
Molecular Weight:
418.44
EC Number:
266-127-0
MDL number:
MFCD00153848
UNSPSC Code:
12352200
PubChem Substance ID:
24277858
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

200

form

powder

color

off-white to yellow

solubility

methanol: 62.5 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: insoluble
H2O: insoluble

originator

Bayer

SMILES string

COCCOC(=O)C1=C(C)NC(C)=C(C1c2cccc(c2)[N+]([O-])=O)C(=O)OC(C)C

InChI

1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3

InChI key

UIAGMCDKSXEBJQ-UHFFFAOYSA-N

Gene Information

human ... ADORA3(140) , CACNA1C(775) , CACNA1D(776) , CACNA1F(778) , CACNA1S(779) , CACNG1(786) , NR3C2(4306)
rat ... Adora1(29290) , Adora2a(25369)

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Application

Nimodipine has been used:
  • as a L-type calcium channel (LTCC) inhibitor, to evaluate its neuroprotective activity in the vibrosections
  • as a standard, in the enantioseparation of chiral drugs by high performance liquid chromatography (HPLC)
  • in the pharmacological studies for the measurement of spine voltage escape

Biochem/physiol Actions

Nimodipine enhances the survival of dopaminergic substantia nigra neurons.
Nimodipine is a potent L-type Ca2+ channel antagonist.

Features and Benefits

This compound is featured on the Calcium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Caution

Photosensitive

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yuri C Martins et al.
Malaria journal, 12, 138-138 (2013-04-27)
Human cerebral malaria (HCM) is a life-threatening complication caused by Plasmodium falciparum infection that continues to be a major global health problem despite optimal anti-malarial treatment. In the experimental model of cerebral malaria (ECM) by Plasmodium berghei ANKA, bolus administration
Dendritic spines prevent synaptic voltage clamp
Beaulieu-Laroche L and Harnett MT
Neuron, 97(1), 75-82 (2018)
Ester Ponzetto et al.
Journal of neurosurgery, 119(5), 1125-1128 (2013-08-27)
The authors describe a rare case of central auditory dysfunction induced by cerebral vasospasm after aneurysmal subarachnoid hemorrhage (SAH). A 55-year-old woman who was admitted after aneurysmal SAH developed cerebral vasospasm on Day 3 affecting mainly the right middle cerebral
Nifedipine and nimodipine protect dopaminergic substantia nigra neurons against axotomy-induced cell death in rat vibrosections via modulating inflammatory responses
Daschil N and Humpel C
Brain Research, 1581, 1-11 (2014)
Karen F S Bell et al.
Journal of neurochemistry, 126(2), 274-287 (2013-02-01)
NMDA-type glutamate receptors mediate both trophic and excitotoxic signalling in CNS neurons. We have previously shown that blocking NMDAR- post-synaptic density-95 (PSD95) interactions provides significant protection from excitotoxicity and in vivo ischaemia; however, the mechanism of neuroprotection is unclear. Here
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