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Apraclonidine hydrochloride

CAS No.
73218-79-8
Chemical Name:
Apraclonidine hydrochloride
Synonyms
APRACLONIDINE HCL;iopidine;AL 02145;alo-2145;Iopidine UD;nc14hydrochloride;iopidineophthalmicsolution;APRACLONIDINE HYDROCHLORIDE;Apracloniding Hydrochloride;P-AMINOCLONIDINE HYDROCHLORIDE
CBNumber:
CB5439290
Molecular Formula:
C9H11Cl3N4
Molecular Weight:
281.57
MDL Number:
MFCD00135922
MOL File:
73218-79-8.mol
MSDS File:
SDS
Last updated:2023-09-04 15:51:00

Apraclonidine hydrochloride Properties

Melting point >2300C
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL Solutions may be stored for several days at 4°C
form solid
color white
Stability Moisture Sensitive
CAS DataBase Reference 73218-79-8(CAS DataBase Reference)
FDA UNII D2VW67N38H

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H300-H370
Precautionary statements  P301+P330+P331+P310-P308+P311
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
HazardClass  6.1(b)
PackingGroup  III
HS Code  2933290000
NFPA 704
0
4 0

Apraclonidine hydrochloride price More Price(33)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR3177 Apraclonidine Hydrochloride pharmaceutical secondary standard, certified reference material 73218-79-8 200MG $534 2024-03-01 Buy
Sigma-Aldrich A0779 p-Aminoclonidine hydrochloride solid 73218-79-8 1MG $92.2 2024-03-01 Buy
Sigma-Aldrich 1041609 Apraclonidine hydrochloride 73218-79-8 100mg $345.2 2024-03-01 Buy
Cayman Chemical 23904 Apraclonidine (hydrochloride) ≥98% 73218-79-8 1mg $37 2024-03-01 Buy
Cayman Chemical 23904 Apraclonidine (hydrochloride) ≥98% 73218-79-8 5mg $161 2024-03-01 Buy
Product number Packaging Price Buy
PHR3177 200MG $534 Buy
A0779 1MG $92.2 Buy
1041609 100mg $345.2 Buy
23904 1mg $37 Buy
23904 5mg $161 Buy

Apraclonidine hydrochloride Chemical Properties,Uses,Production

Chemical Properties

Crystalline Solid

Originator

Alfadrops,Cipla Limited,India

Uses

a-Adrenergic agonist; structural analog of clonidine. Used for treatment of post-surgical elevated intraocular pressure

Uses

Apraclonidine hydrochloride can be used as α-Adrenergic agonist; structural analog of clonidine and be used for treatment of post-surgical elevated intraocular pressure.

Definition

ChEBI: The hydrochloride salt of apraclonidine.

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.

brand name

Iopidine (Alcon).

Therapeutic Function

Antiglaucoma

66711-21-5
73218-79-8
Synthesis of Apraclonidine hydrochloride from Apraclonidine

Apraclonidine hydrochloride Preparation Products And Raw materials

Global( 119)Suppliers
Supplier Tel Email Country ProdList Advantage
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 29220 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 49390 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
Career Henan Chemica Co
+86-0371-86658258 15093356674; laboratory@coreychem.com China 30255 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167 1026@dideu.com China 9320 58
AFINE CHEMICALS LIMITED
0571-85134551 info@afinechem.com CHINA 15377 58
XI'AN TIANGUANGYUAN BIOTECH CO., LTD.
+86-029-86333380 18829239519 sales06@tgybio.com China 959 58
Dayang Chem (Hangzhou) Co.,Ltd.
571-88938639 +8617705817739 info@dycnchem.com CHINA 52867 58
Hebei Duling International Trade Co. LTD
+8618032673083 sales05@hbduling.cn China 15745 58
LEAP CHEM CO., LTD.
+86-852-30606658 market18@leapchem.com China 24738 58

View Lastest Price from Apraclonidine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Apraclonidine hydrochloride pictures 2024-04-17 Apraclonidine hydrochloride
73218-79-8
US $1.10 / g 1g 99.0% min 100 tons min Shaanxi Dideu Medichem Co. Ltd
Apraclonidine hydrochloride USP/EP/BP pictures 2021-09-17 Apraclonidine hydrochloride USP/EP/BP
73218-79-8
US $1.10 / g 1g 99.00% 100 Tons min Dideu Industries Group Limited

Apraclonidine hydrochloride Spectrum

2-(4-amino-2,6-dichlorophenylimino)imidazolidinehydrochloride 2,6-dichloro-n(sup1)-(2-imidazolidinylidene)-1,4-benzenediaminehydrochlorid 2,6-dichloro-n(sup1)-(4,5-dihydro-1h-imidazol-2-yl)-1,4-benzenediaminemonoh 2-[4-AMINO-2,6-DICHLOROANILINO]-2-IMIDAZOLINE HYDROCHLORIDE 2-[(4-AMINO-2,6-DICHLOROPHENYL)IMINO]IMIDAZOLIDINE MONOHYDROCHLORIDE P-AMINOCLONIDINE HYDROCHLORIDE 2,6-Dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)-1,4-benzenediamine Hydrochloride AL 02145 p-Aminoclonidine Monohydrochloride APRACLONIDINE HYDROCHLORIDE 2-(4-Amino-2,6-dichloroanilino)-2-imidazoline hydrochloride, Apraclonidine hydrochloride Iopidine UD (4-amino-2,6-dichloro-phenyl)-(4,5-dihydro-1H-imidazol-2-yl)amine hydrochloride 2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine hydrochloride 2,6-dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine hydrochloride Apraclonidine Hydrochloride (100 mg) 3,5-dichloro-4-(2-imidazolidinylidenimino)anilinehydrochloride 4-benzenediamine,2,6-dichloro-n(sup1)-(4,5-dihydro-1h-imidazol-2-yl)-mono alo-2145 iopidineophthalmicsolution nc14hydrochloride Apracloniding Hydrochloride Apraclonidine hydrochloride Solution in Methanol, 100μg/mL Apraclonidine hydrochloride USP/EP/BP 6-Dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine hydrochloride Apraclonidine Hydrochloride (1041609) APRACLONIDINE HCL iopidine 73218-79-8 3218-79-8 73128-79-8 C9H103N4HCl C9H11Cl3N4 C9H10Cl2N4HCl C9H11Cl3N4C9H10Cl2N4HCl Heterocyclic Compounds Bases & Related Reagents Heterocycles Intermediates & Fine Chemicals Nucleotides Pharmaceuticals