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Apraclonidine

Product Name
Apraclonidine
CAS No.
66711-21-5
Chemical Name
Apraclonidine
Synonyms
NC-14;Aplonidine;Apraclonldine;APRACLONIDINE;4-aminoclonidine;Apraclondine Hcl;Apraclonidine USP/EP/BP;Apraclonidine - API Standards;2-((4-Amino-2,6-dichlorophenyl)imino)imidazolidine;2,6-Dichloro-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
CBNumber
CB3233074
Molecular Formula
C9H10Cl2N4
Formula Weight
245.11
MOL File
66711-21-5.mol
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Apraclonidine Property

Melting point:
>230°
Boiling point:
395.5±52.0 °C(Predicted)
Density 
1.63±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL Solutions may be stored for several days at 4°C
pka
9.26±0.50(Predicted)
form 
solid
color 
white
CAS DataBase Reference
66711-21-5(CAS DataBase Reference)
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Safety

Hazard Codes 
T
Risk Statements 
23/24/25
Safety Statements 
22-36/37/39-45
RIDADR 
UN 2811 6.1/PG 1
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P311Call a POISON CENTER or doctor/physician.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P361Remove/Take off immediately all contaminated clothing.

P363Wash contaminated clothing before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0000395
Product name
APRACLONIDINE
Purity
95.00%
Packaging
1MG
Price
$600.32
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0000395
Product name
APRACLONIDINE
Purity
95.00%
Packaging
10MG
Price
$813.76
Updated
2021/12/16
AvaChem
Product number
2707B
Product name
Apraclonidine
Packaging
5mg
Price
$39
Updated
2021/12/16
AvaChem
Product number
2707B
Product name
Apraclonidine
Packaging
10mg
Price
$59
Updated
2021/12/16
AvaChem
Product number
2707B
Product name
Apraclonidine
Packaging
25mg
Price
$89
Updated
2021/12/16
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Apraclonidine Chemical Properties,Usage,Production

Originator

Alfadrops,Cipla Limited,India

Definition

ChEBI: An imidazoline compound having a 4-amino-2,6-dichloroanilino group at the 2-position.

Manufacturing Process

The preparation of p-aminoclonidine (apraclonidine) consists of 6 steps.
In the first step 2,6-dichloro-4-nitroaniline was converted to 2,6-dicloro-4- nitrophenylisothiocyanate by addition of thiophosgene in toluene according to the method described in Great Britain Patent No.: 1,131,780 (Beck et al.).
The second step involved the conversation of 2,6-dichloro-4-nitrophenylisothiocyanate to 1-(2-aminoethyl)-3-(2,6-dichloro-4-nitrophenyl)-thiourea ethylenediamine solvate. The solution of 2,6-dicloro-4-nitrophenylisothiocyanate (432 g, 1.73 mol) in 2 L of toluene was added dropwise to the cooled (0°C) solution ethylenediamine (244 ml, 3.66 mol, 2.1 eq.) in toluene (4 L) under a nitrogen atmosphere. 2-Propanol (1 L) was added and after 5 minutes, the solid was collected by filtration, washed with 20% 2- propanol/toluene, and dried to a constant weight of 602 g (94%). This product is hygroscopic, mp 120°C (dec.).
The third step was the conversation of 1-(2-aminoethyl)-3-(2,6-dichloro-4- nitrophenyl)-thiourea ethylenediamine solvate to 2-[(2,6-dicloro-4- nitrophenyl)imino]imidazoline ethylenediamine solvate. (500 g, 1.35 mol) of above prepared thiourea solvate was suspended with toluene (4 L) and was heated at reflux for 15 hours. The mixture was cooled to 23°C and 1 M aqueous hydrochloric acid (4 L) was added. After stirring for 10 min the biphasic mixture was filtered to remove a sticky insoluble material. The aqueous phase was neutralized to pH=7.0 using 50% NaOH. After stirring for 1 hour the yellow solid was collected by filtration, washed with water (4 L) and t-butyl methyl ether (2 L) and dried in air to constant weight of 195 g (52%), m.p. 289-292°C.
The fourth step was the conversation of 2-[2,6-dichloro-4-nitrophenyl) imino]imidazoline (150 g, 0.55 mol) in methanol (1,5 L) to 2-[(2,6-dichloro-4- aminophenyl)imino]imidazoline by hydrogen with 30 g Raney nickel catalyst at 23°C for 22 hours. After removing the catalyst hydrogen chloride gas was bubbled into solution until pH of the reaction mixture was 1.0. The solvent was rotary removed in vacuum and the residual solid was slurried with 2- propanol (1 L). The solvent was again removed by rotary evaporation, the cream solid was triturated with 2-propanol (600 ml). After aging for 1 hour, the solid was collected by filtration, washed with 2-propanol and t-butyl methyl ether, and dried for 15 hours at 6°C and t-butyl methyl ether, and dried for 15 hours at 60°C and 20 mm Hg. Yield of dihydrochloride 167 g (96%), mp 260°C (dec.).
The dihydrochloride was converted to the monochloride (step 5) by adding 5 M aqueous sodium hydroxide dropwise to pH=6.5 at 5°C for 2 hours. Yield of hydrochloride 87%.
The last step was recrystallization of product from water. The recrystallized material had m.p. 300°C. Calculated for: C9H10Cl2N4HCl: C, 38.39; H, 3.94; N, 19.90; Cl, 37.78. Found: C, 38.36; H, 3.91; N, 19.83; Cl, 37.77.

Therapeutic Function

Antiglaucoma

General Description

In addition to its therapeutic use as an antihypertensiveagent, clonidine has been found to provide beneficialeffects in several other situations, including glaucoma,spasticity, migraine prophylaxis, opiate withdrawal syndrome,and anesthesia. This has prompted the developmentof analogs of clonidine for specific use in some of the mentionedareas. Two of such examples are apraclonidine andbrimonidine. Apraclonidine does not cross the BBB.However, brimonidine can cross the BBB and hence canproduce hypotension and sedation, although these CNSeffects are slight compared with those of clonidine. CNS effectsof these drugs are correlated well to their log P, pKa,and thus log D value. Both apraclonidine and brimonidineare selective α2-agonists with α1: α2 ratios of 30:1 and1,000:1, respectively. Brimonidine is a much more selectiveα2-agonist than clonidine or apraclonidine and is a firstlineagent for treating glaucoma. Apraclonidines’s primarymechanism of action may be related to a reduction of aqueousformation, whereas brimonidine lowers intraocularpressure by reducing aqueous humor production and increasinguveoscleral outflow. Apraclonidine is used specificallyto control elevations in intraocular pressure that canoccur during laser surgery on the eye. Another example istizanidine (Zanaflex), which finds use in treating spasticityassociated with multiple sclerosis or spinal cord injury. Bystimulating 2-adrenergic receptors, it is believed to decreasethe release of excitatory amino acid NTs from spinalcord interneurons.

Veterinary Drugs and Treatments

Apraclonidine is an alpha2 adrenergic agonist used to reduce aqueous humor secretion. Apraclonidine is a relatively selective, alphaadrenergic agonist and does not have significant membrane stabilizing (local anesthetic) activity. The onset of action is within 3 – 5 hours of a single dose. It apparently is less effective than brimonidine in dogs and is very potent, causing vomiting and diarrhea in cats and dogs. Apraclonidine will reduce aqueous production but must be combined with other agents for adequate control. Neither the beta-blockers nor alpha-agonists are as effective as the carbonic anhydrase inhibitors in decreasing aqueous production.

Apraclonidine Preparation Products And Raw materials

Raw materials

Preparation Products

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Apraclonidine Suppliers

SIGMA-RBI
Tel
--
Fax
--
Country
Switzerland
ProdList
6896
Advantage
91
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View Lastest Price from Apraclonidine manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Apraclonidine 66711-21-5
Price
US $1.10/g
Min. Order
1g
Purity
99.0% min
Supply Ability
100 tons min
Release date
2021-05-13

66711-21-5, ApraclonidineRelated Search:


  • 4-aminoclonidine
  • APRACLONIDINE
  • Apraclonldine
  • 2-((4-Amino-2,6-dichlorophenyl)imino)imidazolidine
  • Apraclondine Hcl
  • 2,6-Dichloro-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
  • 2,6-Dichloro-N-[(4,5-dihydro-1H-imidazol)-2-yl]-1,4-benzenediamine
  • Aplonidine
  • NC-14
  • 2,6-Dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
  • 1,4-Benzenediamine, 2,6-dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)-
  • Apraclonidine USP/EP/BP
  • Apraclonidine - API Standards
  • 66711-21-5