Atipamezole

Product Name: Atipamezole
CAS No.: 104054-27-5
Chemical Name: Atipamezole
Synonyms: MPV-1248;atipamezole;4-(2-Ethyl-2-indanyl)imidazole;5-(2-Ethyl-2-indanyl)-1H-imidazole;5-(2-ethyl-1,3-dihydroinden-2-yl)-1H-imidazole;4-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole;5-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole;1H-Imidazole, 5-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-
CBNumber: CB81324345
Molecular Formula: C14H16N2
Formula Weight: 212.29
MOL File: 104054-27-5.mol

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Atipamezole Property

Melting point:: 126-129oC
Boiling point:: 367.1±11.0 °C(Predicted)
Density: 1.115±0.06 g/cm3(Predicted)
storage temp.: room temp
solubility: DMSO: ≥30mg/mL
form: powder
pka: 14.05±0.10(Predicted)
color: white to brown
InChI: InChI=1S/C14H16N2/c1-2-14(13-9-15-10-16-13)7-11-5-3-4-6-12(11)8-14/h3-6,9-10H,2,7-8H2,1H3,(H,15,16)
InChIKey: HSWPZIDYAHLZDD-UHFFFAOYSA-N
SMILES: C1NC(C2(CC)CC3=C(C2)C=CC=C3)=CN=1
CAS DataBase Reference: 104054-27-5(CAS DataBase Reference)

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A9611
Product name: Atipamezole
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $115
Updated: 2024/03/01

Sigma-Aldrich

Product number: A9611
Product name: Atipamezole
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $462
Updated: 2024/03/01

TRC

Product number: A790095
Product name: Atipamezole
Packaging: 50mg
Price: $525
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA29423
Product name: Atipamezole
Packaging: 2mg
Price: $64.1
Updated: 2021/12/16

AK Scientific

Product number: 2225BA
Product name: Atipamezole
Packaging: 10mg
Price: $66
Updated: 2021/12/16

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Atipamezole Chemical Properties,Usage,Production

Originator

Antisedan,Novartis

Uses

Antagonist (α2-receptor).

Uses

Atipamezole has been used as a α2-adrenoceptor antagonist in mesencephalic trigeminal nucleus (MTN) neurons, CD4+ T-lymphocyte and human embryonic kidney (HEK293) membrane preparation.

Manufacturing Process

(a). 2-Acetyl-1-indanone (Liebigs Ann. Chem. 1906, 347, 112) is alkylated with ethylbromide in acetone in the presence of sodium carbonate to 2-acetyl- 2-ethyl-1-indanone. The acetyl group is brominated with bromine in methanol and to imidazole by heating in formamide as before. The melting point of the 4(5)-(2,3-dihydro-2-ethyl-1-oxo-1H-inden-2-yl)imidazole is 126-127°C (from ethyl acetate).
(b). The carbonyl group of 4(5)-(2,3-dihydro-2-ethyl-1-oxo-1H-inden-2- yl)imidazole is reduced to the alcohol group with sodium borohydride in ethanol. The product is the mixture of cis-trans stereoisomers, the purification of which is accomplished by liquid chromatography: cis-isomer as hydrochloride (melting point 184-185°C), 1H NMR (80 MHz, MeOH-d4): 0.73 (3H, t), 1.86 (2H, m), 3.36 (2H, m), 3.61 (3H, s), 5.15 (1H, s), 7.06 (1H, d), 7.2-7.4 (4H, m), 8.69 (1H, d), and trans-isomer as hydrochloride, 1H NMR (80 MHz, MeOH-d4): 0.80 (3H, t), 1.84 (2H, m), 3.15 (2H, m), 3.24 (3H, s), 5.15 (1H, s), 6.87 (1H, d), 7.2-7.4 (4H, m), 8.54 (1H, d).
The oxo derivative prepared in step (a) or the hydroxy derivative prepared in step (b) is hydrogenated in 2 N hydrochloric acid in the presence of 10% palladium on carbon at 70°C. When the uptake of hydrogen ceases, the reaction mixture is filtered and made alkaline. The product is extracted with methylene chloride which is washed with water, dried and evaporated to dryness. From the residue, which is the product as base, is made the hydrochloride of 4(5)-(2,3-dihydro-2-ethyl-1H-inden-2-yl)imidazole using dry hydrogen chloride in ethyl acetate. It has melting point 211-215°C.

brand name

Antisedan (Farmos Group Ltd., Finland).

Therapeutic Function

Antihypertensive

General Description

Atipamezole has an imidazole structure and gets localized in the central nervous system on administration.

Biochem/physiol Actions

Atipamezole is a selective α2 adrenergic blocker. Atipamezole is more potent than yohimbine; it is very selective for α2 adrenergic vs α1 sites, but not selelctive for α2 subtypes.

Atipamezole Preparation Products And Raw materials

Raw materials

Preparation Products

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Atipamezole Suppliers

Americas 1 China 123 Europe 1 France 1 India 4 Japan 1 The Netherlands 1 United Kingdom 1 United States 13 Global 146

Musechem

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Aladdin Scientific

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Matrix Scientific

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View Lastest Price from Atipamezole manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Atipamezole 104054-27-5
Price: US $0.00/Kg/Bag
Min. Order: 10g
Purity: 98%min
Supply Ability: 10kg
Release date: 2021-12-29

Zhuozhou Wenxi import and Export Co., Ltd

Product: Atipamezole 104054-27-5
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: Atipamezole 104054-27-5
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-08

104054-27-5, AtipamezoleRelated Search:

Ethyl maltol Imidazole Hydroxyethyl starch Ethyl cellulose Albendazole Ethyl formate Ethanol Ethylparaben Hydroxyethyl Cellulose Indene 5-Chloro-1-indanone Levamisole Omeprazole 2-Ethoxyethanol Ethyl acetate Levamisole hydrochloride Cefmetazole Omeprazole sodium sterile

atipamezole

4-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole

4-(2-Ethyl-2-indanyl)imidazole

MPV-1248

5-(2-ethyl-1,3-dihydroinden-2-yl)-1H-imidazole

1H-Imidazole, 5-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-

5-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole

5-(2-Ethyl-2-indanyl)-1H-imidazole

104054-27-5

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