104054-27-5 Usage
Originator
Antisedan,Novartis
Uses
Different sources of media describe the Uses of 104054-27-5 differently. You can refer to the following data:
1. Antagonist (α2-receptor).
2. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 104054-27-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,4,0,5 and 4 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 104054-27:
(8*1)+(7*0)+(6*4)+(5*0)+(4*5)+(3*4)+(2*2)+(1*7)=75
75 % 10 = 5
So 104054-27-5 is a valid CAS Registry Number.
InChI:InChI=1/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)
104054-27-5Relevant articles and documents
Preparation process of atipamezole hydrochloride
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Paragraph 0019-0028; 0030; 0032; 0034; 0036, (2020/12/08)
The invention relates to the technical field of preparation of compounds, in particular to a preparation process of atipamezole hydrochloride. The preparation process comprises the following operationsteps: 1) reacting 4-(2-ethyl-2-indanone) imidazole and alkali in an organic solvent; 2) adding hydrazine hydrate into the reaction solution obtained in the step 1) to obtain atemeconazole; and 3) adding the atemeconazole obtained in the reaction 2) into concentrated hydrochloric acid for salifying to obtain atemeconazole hydrochloride. At present, the industrial synthesis of the atemeconazole hydrochloride in the prior art is low in yield and high in cost; the invention provides a brand-new preparation process of the atenomezole, which effectively improves the reaction efficiency, synthesizes the atenomezole with high selectivity, reduces byproducts, effectively reduces the discharge of waste water and waste gas and is beneficial to industrial production.
