ChemicalBook > CAS DataBase List > Atipamezole

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
American Custom Chemicals Corporation
Product number
INB0004800
Product name
ATIPAMEZOLE
Purity
95.00%
Packaging
5MG
Price
$550
Updated
2021/12/16
Biosynth Carbosynth
Product number
FA29423
Product name
Atipamezole
Packaging
50mg
Price
$769
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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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:


  • 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
  • API