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75438-57-2

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75438-57-2 Usage

Description

Different sources of media describe the Description of 75438-57-2 differently. You can refer to the following data:
1. Moxonidine, also known as Physiotens, is a highly selective imidazoline receptor agonist-Ⅰ by excitement ventrolateral medulla nucleus (RVLM)-Ⅰ type imidazoline receptor in the peripheral sympathetic nerve activity decreased. This receptor subtype is found in both the rostral ventro-lateral pressor and ventromedial depressor areas of the medulla oblongata. Moxonidine therefore causes a decrease in sympathetic nervous system activity and, therefore, a decrease in blood pressure. It is a new type of antihypertensive drug, commonly used in the treatment of essential hypertension. Compared to the older central-acting antihypertensives, moxonidine binds with much greater affinity to the imidazoline I1-receptor than to the α2-receptor. In contrast, clonidine binds to both receptors with equal affinity. It may have a role when thiazides, beta-blockers, ACE inhibitors and calcium channel blockers are not appropriate or have failed to control blood pressure.
2. Moxonidine, which is structurally related to clonidine, is a new centrally acting antihypertensive that acts as a stronger agonist at imidazole receptors and a weaker agonist at α2-adrenergic receptors than clonidine. It is also reported to have less side effects and a much reduced potential to produce a rebound in blood pressure on withdrawal. Clinically, moxonidine appears to have comparable antihypertensive efficacy with the ACE inhibitors and calcium antagonists.

Physical and Chemical Properties

ensity: 1.52g/cm3, boiling point:? 364.7 °C at 760 mmHg, flash point: 174.3 °C, crystallization, melting point: 217-219 degrees Celsius.

Application

By stimulating the central presynaptic alpha 2-receptor and onset, and its antihypertensive effect of ACE inhibitors, calcium antagonists nifedipine and captopril similar. Treatment of essential hypertension. The intervention of renal interstitial fibrosis can protect the kidney.

Preparation

5-amino-4,6-dichloro-2-methyl pyrimidine and 1-acetyl-2-imidazolin-2-one. The product, reacting with sodium methanol can produce moxonidine.

Precautions

There may be dry mouth, fatigue and headache at the beginning of treatment, occasional dizziness, insomnia, and weakness in the legs and so on. Sick sinus syndrome, the sinus node and atrioventricular Ⅱ-Ⅲ degree block, resting bradycardia (50 beats/min), unstable angina, severe liver disease, progressive renal dysfunction, angioedema patients should not use it.

References

https://en.wikipedia.org/wiki/Moxonidine

Chemical Properties

White Solid

Originator

Beiersdorf (Germany)

Uses

Different sources of media describe the Uses of 75438-57-2 differently. You can refer to the following data:
1. Moxonidine is an antihypertensive agent.
2. Antihypertensive;Imidazoline receptor agonist

Brand name

Cynt (Lilly); Nucynt (Lilly); Norcynt (Lilly);Physiotens.

Biological Activity

Mixed I 1 imidazoline receptor and α 2 -adrenergic agonist; displays 40-fold higher affinity for I 1 receptors versus α 2 -adrenoceptors. Centrally acting antihypertensive agent.

Clinical Use

Antihypertensive agent (centrally acting agonist at I1 receptor, imidazoline and alpha2 adrenoceptors)

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

10-20% metabolised, predominantly to 4,5-dehydromoxonidine and to an aminomethanamidine derivative both of which are much less active than moxonidine. Moxonidine and its metabolites are almost entirely eliminated via the kidney. More than 90% of the dose is eliminated in the first 24 hours via the kidney, while approximately 1% is eliminated in the faeces

Check Digit Verification of cas no

The CAS Registry Mumber 75438-57-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,4,3 and 8 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 75438-57:
(7*7)+(6*5)+(5*4)+(4*3)+(3*8)+(2*5)+(1*7)=152
152 % 10 = 2
So 75438-57-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H12ClN5O/c1-5-13-7(10)6(8(14-5)16-2)15-9-11-3-4-12-9/h3-4H2,1-2H3,(H2,11,12,15)

75438-57-2 Well-known Company Product Price

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

  • (M2660)  Moxonidine  >98.0%(T)

  • 75438-57-2

  • 200mg

  • 690.00CNY

  • Detail
  • TCI America

  • (M2660)  Moxonidine  >98.0%(T)

  • 75438-57-2

  • 1g

  • 2,450.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000226)  Moxonidine  European Pharmacopoeia (EP) Reference Standard

  • 75438-57-2

  • Y0000226

  • 1,880.19CNY

  • Detail

75438-57-2SDS

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 4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidin-5-amine

1.2 Other means of identification

Product number -
Other names Lomox

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:75438-57-2 SDS

75438-57-2Synthetic route

mono-Moxonidine oxalate
287099-40-5

mono-Moxonidine oxalate

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

C

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 1h; pH=10 - 11; Product distribution / selectivity;A n/a
B n/a
C 94%
methanol
67-56-1

methanol

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

A

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
With potassium carbonate at 65℃; for 3h; Product distribution / selectivity;A n/a
B 90.7%
methanol
67-56-1

methanol

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

C

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 65℃; for 6h; Product distribution / selectivity;A n/a
B n/a
C 88.3%
With potassium hydrogencarbonate In water at 65℃; for 10h; Product distribution / selectivity;A n/a
B n/a
C 88.3%
With potassium hydroxide; potassium carbonate at 20℃; for 16h; Product distribution / selectivity;A n/a
B n/a
C 85.9%
methanol
67-56-1

methanol

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 24h; Product distribution / selectivity;A n/a
B 88.3%
With potassium hydroxide at 25℃; for 12h; Product distribution / selectivity;A n/a
B 88.3%
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

sodium methylate
124-41-4

sodium methylate

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

C

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
In methanol at 0 - 65℃; for 1.5 - 48h; Product distribution / selectivity;A n/a
B n/a
C 84.7%
In tetrahydrofuran at 25℃; for 30h; Product distribution / selectivity;A n/a
B n/a
C 76.4%
In toluene at 25℃; for 30h; Product distribution / selectivity;A n/a
B n/a
C 66.8%
methanol
67-56-1

methanol

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
With pyrographite; 1,8-diazabicyclo[5.4.0]undec-7-ene at 65℃; for 3.5h;84.4%
With potassium hydroxide at 20℃; for 30h; Product distribution / selectivity;83.5%
With tetrabutylammomium bromide; water; sodium hydroxide In dichloromethane at 20 - 35℃; for 2.5h; pH-value; Reagent/catalyst; Solvent; Temperature;3.43 g
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 20℃; for 31h;83.5%
With sodium methylate In methanol; water
In tetrahydrofuran; methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

sodium methylate
124-41-4

sodium methylate

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
In methanol at 0℃; for 48h; Product distribution / selectivity;A n/a
B 77.6%
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

sodium methylate
124-41-4

sodium methylate

A

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; for 30h; Product distribution / selectivity;A n/a
B 76.4%
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

C

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
Stage #1: 4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine With potassium carbonate In methanol at 47 - 52℃; for 5h;
Stage #2: With water; acetic acid In methanol for 0.5h;
Stage #3: With ammonia In methanol; water for 1h; Product distribution / selectivity;
methanol
67-56-1

methanol

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

1-[1-((4,6-dichloro-2-methyl-pyrimidin-5-yl)imino)-ethyl]-imidazolidin-2-one
438000-58-9

1-[1-((4,6-dichloro-2-methyl-pyrimidin-5-yl)imino)-ethyl]-imidazolidin-2-one

sodium methylate
124-41-4

sodium methylate

A

1-[1-[(4-chloro-2-methyl-6-methoxy-pyrimidin-5-yl)imino]ethyl]-imidazolidin-2-one
1033401-62-5

1-[1-[(4-chloro-2-methyl-6-methoxy-pyrimidin-5-yl)imino]ethyl]-imidazolidin-2-one

B

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
at 20℃;A 0.12 %Chromat.
B 96.66 %Chromat.
methanol
67-56-1

methanol

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

sodium methylate
124-41-4

sodium methylate

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

C

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
for 2h; Heating / reflux;A 1.45 - 1.48 %Chromat.
B 5.27 - 5.32 %Chromat.
C 93.22 - 93.25 %Chromat.
methanol
67-56-1

methanol

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
75438-54-9

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

sodium methylate
124-41-4

sodium methylate

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
at 30 - 35℃; for 0.75h;520 mg
5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine
88474-31-1

5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium carbonate; trichlorophosphate / dimethyl sulfoxide / 49 h / 5 - 60 °C / Inert atmosphere
2: hydrogenchloride / isopropyl alcohol / 8 h / 20 °C
3: base / water / pH 9
View Scheme
4-chloro-6-methoxy-2-methyl-5-(2-imidazolin-2-yl)aminopyrimidine hydrochloride

4-chloro-6-methoxy-2-methyl-5-(2-imidazolin-2-yl)aminopyrimidine hydrochloride

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
With base In water pH=9;
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine
88474-31-1

5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine

moxonidine
75438-57-2

moxonidine

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine With sodium carbonate; trichlorophosphate In dimethyl sulfoxide at 5 - 60℃; for 50.5h; Cooling with acetone-dry ice; Inert atmosphere;
Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; for 8h;
oxalic acid
144-62-7

oxalic acid

moxonidine
75438-57-2

moxonidine

A

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

mono-Moxonidine oxalate
287099-40-5

mono-Moxonidine oxalate

Conditions
ConditionsYield
In methanol; diethyl ether Product distribution / selectivity; Heating / reflux;A n/a
B 95%
In methanol; propan-1-ol at 0 - 20℃; for 3.5h; Product distribution / selectivity; Heating / reflux;A n/a
B 83.6%
In propan-1-ol; dimethyl sulfoxide Product distribution / selectivity; Heating / reflux;A n/a
B 58%
formic acid
64-18-6

formic acid

moxonidine
75438-57-2

moxonidine

A

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

mono-Moxonidine formate
1008754-14-0

mono-Moxonidine formate

Conditions
ConditionsYield
In propan-1-ol at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux;A n/a
B 92.7%
In isopropyl alcohol at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux;A n/a
B 85%
In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux;A n/a
B 84%
In dimethyl sulfoxide at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux;A n/a
B 66%
oxalic acid
144-62-7

oxalic acid

moxonidine
75438-57-2

moxonidine

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

mono-Moxonidine oxalate
287099-40-5

mono-Moxonidine oxalate

Conditions
ConditionsYield
In propan-1-ol at 0 - 20℃; for 2h; Product distribution / selectivity; Heating / reflux;A n/a
B 87.3%
oxalic acid
144-62-7

oxalic acid

moxonidine
75438-57-2

moxonidine

A

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
352457-35-3

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

B

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
75439-01-9

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

C

mono-Moxonidine oxalate
287099-40-5

mono-Moxonidine oxalate

Conditions
ConditionsYield
In methanol; propan-1-ol at 0 - 20℃; for 3.5h; Heating / reflux;A n/a
B n/a
C 87%
moxonidine
75438-57-2

moxonidine

4-methoxy-2-methyl-6-methylthio-5-(2-imidazolin-2-yl)-aminopyrimidine
75438-60-7

4-methoxy-2-methyl-6-methylthio-5-(2-imidazolin-2-yl)-aminopyrimidine

Conditions
ConditionsYield
In toluene

75438-57-2Relevant articles and documents

SYNTHESIS OF SUBSTITUTED AMINOPYRIMIDINES

-

Page/Page column 17; 18, (2015/02/19)

The present invention relates to a novel process for the manufacture of certain substituted aminopyrimidines having Formula (I) or a tautomer or salt thereof, wherein R1 is selected from hydrogen, halogen, C1-4alkoxy, C1-4alklthio, C1-4alkyl, C3-5cycloalkyl, for example R1 is halogen such as chloro; R2 is C1-4alkyl, for example methyl, ethyl, i-propyl, n-propyl or butyl (any isomer), such as methyl; and R3 is selected from hydrogen, C1-4alkoxy, C1-4alkylthio, C1-4alkyl, C3-5cycloalkyl, for example C1-4alkyl such as methyl, ethyl, i-propyl, n-propyl or butyl (any isomer), for example methyl; crystalline forms thereof as well as chemical intermediates suitable for use in performing the process.

PROCESS FOR THE PRODUCTION OF MOXONIDINE

-

Paragraph 0057-0058, (2014/08/19)

4,6-dichloro-2-methyl-5-(1-acyl-2-imidazolin-2-yl)-aminopyrimidine is reacted with methanol in the presence of a non-ionic organic base, and moxonidine is obtained directly from the reaction mixture.

Process for the preparation of moxonidine

-

Paragraph 0037, (2013/05/09)

The present invention provides an improved process for the preparation of 4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)aminopyrimidine. The present invention also provides an improved process for the preparation of moxonidine. The present invention further provides a process for the purification of moxonidine.

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