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66085-59-4 Usage

Calcium channel blockers

Nimodipine, molecular formula C21H26N2O7, was first developed by Germany Bayer pharmaceutical industry. It is the latest generation of 1,4-dihydropyridine calcium channel blocker that is calcium blockers. It can inhibit the influx of calcium into vascular smooth muscle cells. It has bronchodilation effects isolated or intracorporal cerebral artery or ischemia cerebral artery. It can significantly improve cerebral blood flow, and effectively prevent and treat cerebral ischemic damage, migraines, sudden deafness that caused by cerebral vascular spasm which is induced by subarachnoid hemorrhage. Nimodipine can also be used for mild and moderate hypertension. It can effectively regulate the body's calcium in order to maintain the normal physiological function. It has particularly prominent effects on cerebral vascular, and it can combine with specific receptors of central nervous system. Cerebral vessels can be selectively expanded at a suitable dose, and it can hardly affect peripheral vascular. It also has a good effect on high blood pressure when its dose is increased. The above information is edited by the lookchem of Ge Qian.

Pharmacological action

Nimodipine is calcium channel blockers. It can relieve vasospasm by effectively preventing Ca2+ into the cell and inhibiting contraction of smooth muscle. It is highly lipophilic, and easily permeates the blood-brain barrier. It has a strong effect on cerebral artery. In addition, it also has positive effect on protecting memory and recovering intelligence. Nimodipine has selective effects on cerebrovascular smooth muscle. It can expand cerebral blood vessels, increase cerebral blood flow and significantly reduce ischemic brain damage caused by vasospasm.

Pharmacokinetics

1. When taken orally, nimodipine can be rapidly absorbed after oral administration, and the concentration will reach a peak within about 1 hour. T1/2 is 1 to 2 hours, and the elimination time is 8 to 9 hours. After taken orally four times a day, the blood has no obvious accumulation of nimodipine for seven days. When its concentration is between 10ng/L and 10μg/mL, more than 95% of drugs combine with plasma protein. Most of nimodipine will be excreted in the form of metabolites after oral, and about 1% of the ingredients exit the body unchanged in the urine. Due to the rapid metabolism of nimodipine in a first phase, the bioavailability after taken orally is 13%. The biological activity of nimodipine in patients with chronic liver damage increases. And the maximum concentration can be up to twice as high as normal people. 2. Intravenous injection: The dosage for intravenous injection is 0.03mg/kg. The half-life (t1/2) is (1.1±0.2) h. According to the study, 15 patients with subarachnoid space bleeding (grade 1-3) have been injected with this product for 48mg a day, lasting 14 days. The average plasma concentration is 36~ 72μg/L. The protein binding rate is 96% to 99%. The steady state distribution of apparent volume is 1.6~3.1L/kg. The concentration of plasma drug decline quickly, and the metabolites almost has no activity. It is mainly eliminated through bile. 80% can be excreted by the intestine with faeces and 20% by the kidneys with the urine.

Synthesis route

The first step: using hydrogen chloride, concentrated sulfuric acid or acetic acid-piperidine as a catalyst, m-nitrobenzaldehyde (2) and 2-methoxy-ethyl acetoacetate (3) generate 2-(3-nitrobenzylidene) ethyl 2-methoxyethyl acetoacetate (4) by condensation. The second step: concentrated hydrochloric acid and absolute ethanol are heated to the reflux reaction conditions under nitrogen. (4) and 3-amino butyric acid isopropyl ester (5) are heated to obtain crude product of (1). After cooling crystallization, pumping filtered, the filter cake is washed with cold ethanol. Then it is dried to get pale yellow crystals nimodipine (1). Figure 1: Synthesis route of nimodipine

Indications

Nimodipine is a calcium antagonist of selective expansion of cerebral blood vessels. It can increase cerebral blood flow, improve cerebral blood circulation, prevent ischemic cerebral vasospasm, reduce calcium influx, protect ischemic brain cell function, prevent the occurrence and development of brain vascular disease and delay and prevent the occurrence of stroke. Nimodipine is mainly used for cerebral insufficiency, cerebral vasospasm, subarachnoid hemorrhage, stroke and migraine. It has a certain effect on sudden deafness.

Attentions

1.Nimodipine should be used for patients with cerebral edema and intracranial hypertension with caution. Nimodipine metabolites has toxicity. So patients with liver dysfunction should be used with caution. Nimodipine can cause a lowering of blood pressure. For patients with hypertensive subarachnoid hemorrhage or stroke patients, the dosage of antihypertensive drugs should be paid attention to be reduced or temporarily stopped, or the dosage of nimodipine should be reduced. That can produce intestinal pseudo-obstruction, manifested as abdominal distension, decreased bowel sounds. When the above symptoms appears, the dosage should be reduced and observation should be hold. 2.Nimodipine can be secreted by milk. Breast-feeding women should not use. Animal experiments suggest that this product has teratogenicity.

Untoward reaction

There are about 11.2% of patients with subarachnoid hemorrhage that have adverse reactions. The most common symptoms are blood pressure dropping (the extent of decline is related to drug dose), hepatitis, skin irritation, gastrointestinal bleeding, thrombocytopenia, occasionally transient dizziness, headache, facial flushing, vomit, gastrointestinal discomfort and the like. In addition, after taken nimodipine orally, individual patients may appear alkaline phosphatase (ALP), lactate dehydrogenase (LDH), blood sugar elevating and platelet count increasing for individual human.

Usage and dosage

The usage and dosage of this product is very different for different symptom and severity. 1. Nimodipine can be taken orally when symptoms are mild: Ischemic cerebrovascular disease: 20~40mg, 3 times/d, continuous use for a month. Migraine: 40mg, 3 times/d; 12 weeks for a course of treatment. Hypertension: 40~80mg, 3 times/d. Sudden deafness: 10~20mg, 3 times/d; 5 days as a course of treatment, usually for 3 to 4 courses. Cerebral vasospasm caused by subarachnoid hemorrhage: 10~20mg, 3~4 times/d; 3 to 4 weeks for a course of treatment. 2. Severe patients with the above-mentioned diseases may be considered to use ntravenous injection: the beginning of 0.5mg/h, gradually increase after 2h to 1~2mg/h; 5~10d later change to oral.

Chemical property

Light yellow crystalline powder, odorless and tasteless. Soluble in ethanol or acetone, insoluble in water. Melting point 124~128℃. Acute toxicity LD50 in mice and rats (mg/kg): 3562, 6599. Oral: 33. Intravenous injection: 16. (+)-Configuration: [α] D20+7.9° (C=0.439, dioxane). (-)-Configuration: [α] D20-7.93° (C=0.374, dioxane).

Uses

Different sources of media describe the Uses of 66085-59-4 differently. You can refer to the following data:
1. 1. Calcium channel blockers. Nimodipine has anti-ischemic and anti-vasoconstriction effect. It is the drug to improve cerebral vasodilator and brain function. It can be used for treating ischemic cerebrovascular disease, mild to moderate hypertension, migraine, cerebral vasospasm, sudden deafness and the like. 2. Calcium channel blockers. Nimodipine is mainly used for the treatment of ischemic cerebrovascular disease and migraine. 3. A new calcium antagonist. Nimodipine is used for the treatment of cerebrovascular disorders, such as cerebral vasospasm, interim and early ischemic cerebrovascular migraine, and sudden deafness.
2. A dihydropyridine calcium channel blocker. It is used as a vasodilator (cerebral).
3. provitamin, antixerophthalamic
4. Nimodipine has been used:as a L-type calcium channel (LTCC) inhibitor, to evaluate its neuroprotective activity in the vibrosectionsas 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
5. Used as a cerebral vasodilator. A dihydropyridine calcium channel blocker

Production method

Method 1: Nimodipine can be synthesized from nitrobenzaldehyde first by condensation with methoxyethyl acetoacetate catalyzed by hydrochloric acid or concentrated sulfuric acid, and then heated with 3-amino butyric acid isopropyl ester in ethanol by cyclization. Method 2: Nitrobenzaldehyde and isopropyl acetoacetate also can be dissolved with stirring at room temperature firstly. Then add glacial acetic acid and piperidine and stir at 40-50℃ to solidify (about 6~7h). After processing for 4h at 40-50℃, 95% ethanol is added, and then heated under reflux until the solid dissolved. Cooled to 0~5℃, precipitated crystals can be filtered and dried to give 2-(3-nitrophenyl methylene) acetyl isopropyl acetate. The yield is 90.6%. Then it reacts with 3-amino butyric acid and 2-methoxy-ethyl ester to obtain the crude product. The crude product can be recrystallized from ethanol to get nimodipine. The yield is 84%, and the melting point is 125~126℃. The second step can also be carried out as follows: 3.8g 2-(3-nitrophenyl methylene) acetyl isopropyl acetate, 8g 2-methoxy-ethyl acetoacetate and 6ml of concentrated ammonia are heated at reflux for 8h in 80ml of ethanol. The product is recrystallized with petroleum ether-ethyl acetate to obtain nimodipine. The yield is 49%, and the melting point is 125℃.

Description

Nimodipine is a cerebral vasodilating calcium antagonist related to nifedipine. It is indicated for the prophylaxis and treatment of neurological deficits due to cerebral vasospasm after subarachnoid hemorrhage.

Chemical Properties

Crystalline Solid

Originator

Bayer (W. Germany)

Definition

ChEBI: A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.

Manufacturing Process

After 8 hours boiling of solution of 3.8 g of 3'-nitro-benzylideneacetoacetic acid isopropylester, 8 grams of acetoacetic acid β-metoxyethyl ester and 6 ml conc ammonia in 80 ml ethanol under reflux, 2,6-dimethyl-4-(3'-nitrophenyl)- 1,4-dihydropyridine 3-β-methoxyethyl ester 5-isopropyl ester of melting point 125°C (petroleum ether/ acetic ester) was obtained. Yield 49% of theory.

Brand name

Nimotop (Bayer).

Therapeutic Function

Vasodilator

General Description

Nimodipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)- 3,5-pyridinedicarboxylic acid 2-methoxyethyl1-methylethyl ester (Nimotop), is another dihydropyridinecalcium channel blocker but differs in that it dilatesthe cerebral blood vessels more effectively than do the otherdihydropyridine derivatives. This drug is indicated for treatmentof subarachnoid hemorrhage-associated neurologicaldeficits.

Biological Activity

L-type Ca 2+ channel blocker.

Biochem/physiol Actions

Nimodipine enhances the survival of dopaminergic substantia nigra neurons.

Clinical Use

Calcium-channel blocker: Prevention and treatment of ischaemic neurological deficits following subarachnoid haemorrhage

Drug interactions

Potentially hazardous interactions with other drugs Aminophylline: possibly increases aminophylline concentration. Anaesthetics: enhanced hypotensive effect. Antibacterials: metabolism accelerated by rifampicin; metabolism possibly inhibited by clarithromycin, erythromycin and telithromycin. Antidepressants: enhanced hypotensive effect with MAOIs . Antiepileptics: effect reduced by carbamazepine, barbiturates, phenytoin and primidone. Antifungals: metabolism possibly inhibited by itraconazole and ketoconazole; negative inotropic effect possibly increased with itraconazole. Antihypertensives: enhanced hypotensive effect, increased risk of first dose hypotensive effect of post synaptic alpha-blockers. Antivirals: concentration possibly increased by ritonavir; use telaprevir with caution. Grapefruit juice: concentration increased - avoid. Theophylline: possibly increased theophylline concentration.

Metabolism

Nimodipine is extensively metabolised in the liver via the cytochrome P450 isoenzyme CYP3A4. It is eliminated as metabolites, mainly by dehydrogenation of the dihydropyridine ring and oxidative O-demethylation. Oxidative ester cleavage, hydroxylation of the 2- and 6-methyl groups, and glucuronidation as a conjugation reaction are other important metabolic steps. The three primary metabolites occurring in plasma show no or only therapeutically negligible residual activity. The metabolites are excreted about 50% renally and 30% in faeces via the bile.

References

1) Cohen and McCarthy (1987),?Nimodipine block of calcium channels in rat anterior pituitary cells; J. Physiol.,?387?195 2) Batuecas?et al.?(1998),?Effects of chronic nimodipine on working memory of old rats in relation to defects in synaptosomal calcium homeostasis; Eur. J. Pharmacol.,?350?141 3) LeVere?et al.?(1989),?Recovery of function after brain damage: facilitation by the calcium entry blocker nimodipine; Behav. Neurosci.,?103?561 4) Herzfeld?et al.?(2014),?Investigation of the neuroprotective impact of nimodipine on Neuro2a cells by means of a surgery-like stress model; Int. J. Mol. Sci.,?15?18453 5) Schampel?et al.?(2017),?Nimodipine fosters remyelination in a mouse model of multiple sclerosis and induces microglia-specific apoptosis; Proc. Natl. Acad. Sci. USA,?114?E3295 6) Allen?et al.?(1983),?Cerebral arterial spasm – a controlled trial of nimodipine in patients with subarachnoid hemorrhage; N. England J. Med.,?308?619

Check Digit Verification of cas no

The CAS Registry Mumber 66085-59-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,0,8 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 66085-59:
(7*6)+(6*6)+(5*0)+(4*8)+(3*5)+(2*5)+(1*9)=144
144 % 10 = 4
So 66085-59-4 is a valid CAS Registry Number.
InChI:InChI=1/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/h6-8,11-12,17,19H,9-10H2,1-5H3/t17?,19-/m0/s1

66085-59-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (N0896)  Nimodipine  >98.0%(HPLC)

  • 66085-59-4

  • 1g

  • 790.00CNY

  • Detail
  • TCI America

  • (N0896)  Nimodipine  >98.0%(HPLC)

  • 66085-59-4

  • 5g

  • 2,590.00CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1293)  Nimodipine  pharmaceutical secondary standard; traceable to USP, PhEur and BP

  • 66085-59-4

  • PHR1293-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (N0850000)  Nimodipine  European Pharmacopoeia (EP) Reference Standard

  • 66085-59-4

  • N0850000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001784)  Nimodipine for peak identification  EuropePharmacopoeia (EP) Reference Standard

  • 66085-59-4

  • Y0001784

  • 1,880.19CNY

  • Detail
  • USP

  • (1463858)  Nimodipine  United States Pharmacopeia (USP) Reference Standard

  • 66085-59-4

  • 1463858-125MG

  • 4,326.66CNY

  • Detail
  • Sigma

  • (N149)  Nimodipine  

  • 66085-59-4

  • N149-100MG

  • 869.31CNY

  • Detail
  • Sigma

  • (N149)  Nimodipine  

  • 66085-59-4

  • N149-500MG

  • 3,410.55CNY

  • Detail

66085-59-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name nimodipine

1.2 Other means of identification

Product number -
Other names Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

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:66085-59-4 SDS

66085-59-4Synthetic route

isopropyl 3-aminocrotonate
40100-28-5

isopropyl 3-aminocrotonate

(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate
39562-22-6

(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
In ethanol for 24h; Heating;81%
2-methoxyethyl-3-oxobutanoate
22502-03-0

2-methoxyethyl-3-oxobutanoate

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

isopropyl β-aminocrotonate
143093-33-8

isopropyl β-aminocrotonate

A

nimodipin
66085-59-4

nimodipin

B

3,5-diisopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
21881-78-7

3,5-diisopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Conditions
ConditionsYield
In ethanol for 16h; Heating;A 69%
B n/a
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

2-methoxyethyl-3-oxobutanoate
22502-03-0

2-methoxyethyl-3-oxobutanoate

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
With pyridine; 4 A molecular sieve; polysterene-based acid-cleavable Rink amine resin; trifluoroacetic acid 1) CH2Cl2, rt, 3 d; 2) 45 deg C, 24 h; 3) CH2Cl2, 45 min;; Yield given. Multistep reaction;
With ammonium acetate In ethanol at 80℃; for 2h; Hantzsch Pyridine Synthesis;
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NH3 (gas.) / 10 °C
2: 81 percent / ethanol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ammonia
2: ethanol / Reflux
View Scheme
2-methoxyethyl-3-oxobutanoate
22502-03-0

2-methoxyethyl-3-oxobutanoate

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77.5 percent / hydrogen chloride / toluene / 20 h / 10 °C
2: 81 percent / ethanol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ammonium hydroxide
2: piperidine / propionic acid / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: piperidine; acetic acid
2: ethanol / Reflux
View Scheme
(+)-1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl-2(S)-methoxy-2-phenylethyl ester

(+)-1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl-2(S)-methoxy-2-phenylethyl ester

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
With sodium In 2-methoxy-ethanol; water
(-)-1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl-2(R)-methoxy-2-phenylethyl ester

(-)-1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl-2(R)-methoxy-2-phenylethyl ester

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
With sodium In 2-methoxy-ethanol; water
(2′-methoxyethyl)-3-amino-3-methylacrylate

(2′-methoxyethyl)-3-amino-3-methylacrylate

3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester
39562-25-9

3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
With piperidine In propionic acid Reflux; Inert atmosphere;
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate
39562-22-6

(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate

nimodipin
66085-59-4

nimodipin

Conditions
ConditionsYield
In ethanol Reflux;
nimodipin
66085-59-4

nimodipin

3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
155861-24-8

3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 25℃; under 2844.3 Torr; for 2h;95%
With hydrogen In tetrahydrofuran; water at 120℃; under 37503.8 Torr; for 17h; chemoselective reaction;95%
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 6h; Solvent; Inert atmosphere; Green chemistry; chemoselective reaction;90%
nimodipin
66085-59-4

nimodipin

carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

C23H27ClN2O9

C23H27ClN2O9

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere; Cooling with ice;95%
Stage #1: nimodipin With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: carbonochloridic acid, chloromethyl ester In tetrahydrofuran at 20℃;
94.84%
nimodipin
66085-59-4

nimodipin

3-isopropyl 5-(2-methoxyethyl) 2,6-bis(methyl-d3)-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

3-isopropyl 5-(2-methoxyethyl) 2,6-bis(methyl-d3)-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With TFA-d; water-d2 In 1-methyl-pyrrolidin-2-one at 50℃; for 24h; Schlenk technique; Inert atmosphere;94%
nimodipin
66085-59-4

nimodipin

Nimodipine Oxidized
85677-93-6

Nimodipine Oxidized

Conditions
ConditionsYield
With potassium carbonate; eosin Y bis(tetrabutyl ammonium salt) In methanol; water at 20℃; for 12h; Irradiation; Green chemistry;78%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 12h;78.4%
With nitric acid at 100℃; for 1h;71%
formaldehyd
50-00-0

formaldehyd

nimodipin
66085-59-4

nimodipin

4-(3-Dimethylamino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

4-(3-Dimethylamino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

Conditions
ConditionsYield
With formic acid; triethylamine In water; tert-butyl alcohol at 100℃; for 30h;77%
With sodium carbonate In water; dimethyl sulfoxide at 130℃; for 15h; Schlenk technique; Sealed tube; Green chemistry;48%
nimodipin
66085-59-4

nimodipin

di-tert-butyl chloromethyl phosphate
229625-50-7

di-tert-butyl chloromethyl phosphate

C30H45N2O11P

C30H45N2O11P

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;55%
carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

nimodipin
66085-59-4

nimodipin

C24H29ClN2O9

C24H29ClN2O9

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at -40 - 20℃;52.7%
nimodipin
66085-59-4

nimodipin

N-nitroso-nimodipine

N-nitroso-nimodipine

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 37℃; for 6h; pH=3 - 3.5;45%
nimodipin
66085-59-4

nimodipin

2,6-Dimethyl-4-(4-nitro-phenyl)-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester
144476-58-4

2,6-Dimethyl-4-(4-nitro-phenyl)-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

Conditions
ConditionsYield
In ethanol; water for 60h; Irradiation;
nimodipin
66085-59-4

nimodipin

A

(S)-Nimodipine
77940-92-2

(S)-Nimodipine

B

(R)-Nimodipine
77940-93-3

(R)-Nimodipine

Conditions
ConditionsYield
With α1-acid glycoprotein HPLC column resolution of racemate;
With Chiralpak IC In hexane; isopropyl alcohol Reagent/catalyst; Solvent; Resolution of racemate;
With trifluoroacetic acid In methanol; isopropyl alcohol at 35℃; under 103432 Torr; Reagent/catalyst; Resolution of racemate; Supercritical conditions;
nimodipin
66085-59-4

nimodipin

C4H9N2*ClH

C4H9N2*ClH

Nimodipine Oxidized
85677-93-6

Nimodipine Oxidized

Conditions
ConditionsYield
In ethanol at 37℃; for 2h; pH=7.4; Kinetics; Further Variations:; Reaction partners; Solvents;
nimodipin
66085-59-4

nimodipin

C4H9N2O2*ClH

C4H9N2O2*ClH

Nimodipine Oxidized
85677-93-6

Nimodipine Oxidized

Conditions
ConditionsYield
With Britton-Robinson buffer In water; N,N-dimethyl-formamide at 37℃; pH=7.4; Kinetics;
nimodipin
66085-59-4

nimodipin

A

2,6-dimethyl-4-(3-nitroso-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

2,6-dimethyl-4-(3-nitroso-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

B

Nimodipine Oxidized
85677-93-6

Nimodipine Oxidized

Conditions
ConditionsYield
In methanol Quantum yield; Product distribution; Further Variations:; Solvents; wavelengths; presence of air; Irradiation;
nimodipin
66085-59-4

nimodipin

A

2,6-dimethyl-4-(3-nitroso-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

2,6-dimethyl-4-(3-nitroso-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

B

2-Methoxyethyl 1-Methylethyl 1,4-Dihydro-2,6-dimethyl-4-(3-hydroxylaminophenyl)-3,5-pyridinedicarboxylate
116799-92-9

2-Methoxyethyl 1-Methylethyl 1,4-Dihydro-2,6-dimethyl-4-(3-hydroxylaminophenyl)-3,5-pyridinedicarboxylate

C

Nimodipine Oxidized
85677-93-6

Nimodipine Oxidized

D

3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
155861-24-8

3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With triethylamine In acetonitrile Quantum yield; Irradiation;
chromium(VI) oxide
1333-82-0

chromium(VI) oxide

nimodipin
66085-59-4

nimodipin

Nimodipine Oxidized
85677-93-6

Nimodipine Oxidized

Conditions
ConditionsYield
In acetic acid
In acetic acid
nimodipin
66085-59-4

nimodipin

C25H31N3O11*ClH

C25H31N3O11*ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice
2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 5 h / 55 - 60 °C
3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 5 h / 20 °C
View Scheme
nimodipin
66085-59-4

nimodipin

C26H33N3O11*ClH

C26H33N3O11*ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice
2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 55 - 60 °C
3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 2 h / 20 °C
View Scheme
nimodipin
66085-59-4

nimodipin

C26H33N3O11*ClH

C26H33N3O11*ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice
2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 4 h / 55 - 60 °C
3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 2 h / 20 °C
View Scheme
nimodipin
66085-59-4

nimodipin

C29H39N3O11*ClH

C29H39N3O11*ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice
2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 50 - 60 °C
3: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 4 h / 20 °C
View Scheme

66085-59-4Relevant articles and documents

METHODS FOR TREATING CHRONIC FATIGUE SYNDROME AND MYALGIC ENCEPHALOMYELITIS

-

, (2021/03/13)

In one aspect the invention relates to a method of treatment selected from the group consisting of: (a) treating a symptom such as pain in a subject identified or diagnosed as having Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS); (b) treating a symptom such as pain in a subject having dysfunctional TRPM3 ion channel activity; (c) restoring NK cell function in a subject having dysfunctional TRPM3 ion channel activity; and (d) restoring calcium homeostasis in a subject having dysfunctional TRPM3 ion channel activity. The method comprises the step of administering to the subject a therapeutically effective amount of at least one therapeutic compound selected from the group consisting of: (i) an opioid receptor antagonist; (ii) an opioid antagonist; and (iii) a therapeutic compound that restores TRPM3 ion channel activity. In some embodiments the therapeutic compound is naltrexone hydrochloride.

Metal-free-mediated oxidation aromatization of 1,4-dihydropyridines to pyridines using visible light and air

Wei, Xiaojing,Wang, Lin,Jia, Wenliang,Du, Shaofu,Wu, Lizhu,Liu, Qiang

supporting information, p. 1245 - 1250 (2015/02/05)

A metal-free and environmentally friendly aerobic aromatization photosensitized by organic dye eosin Y bis(tetrabutyl ammonium salt) (TBA-eosinY) has been developed. With the aid of K2CO3, the aerobic catalytic system converts 1,4-dihydropyridines to their corresponding pyridine derivatives efficiently under visible light irradiation (λ=450 nm) at room temperature.

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.

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