1249-84-9 Usage
Description
Azacosterol hydrochloride, a diaza derivative of cholesterol, functions as a hypocholesteremic agent. It operates by inhibiting the enzyme delta-24-reductase, which results in the accumulation of desmosterol.
Uses
Used in Pharmaceutical Industry:
Azacosterol is used as a hypocholesteremic agent for reducing high cholesterol levels. By blocking delta-24-reductase, it promotes the accumulation of desmosterol, thus helping to manage cholesterol levels in the body.
Used in Avian Industry:
Azacosterol is used as a chemosterilant for avian species. It serves to control the population of certain bird species by chemically inducing sterility, which can be beneficial for managing overpopulation and its associated ecological impacts.
Originator
Ornitrol,Avitrol Corporation
Manufacturing Process
A solution of 15 parts of 3β-hydroxyandrost-5-en-17-one and 30 parts of 3-
dimethylaminopropylamine in 36.6 parts of formic acid is heated in an oil bath
at about 170-180°C for about 24 hours. The cooled mixture is diluted with
about 500 parts of water, and the resulting aqueous mixture is extracted with
chloroform, containing a small amount of methanol. The organic layer is
separated, washed with water, dried over anhydrous sodium sulfate, and
evaporated to dryness under reduced pressure. The viscous residue is
dissolved in a mixture of 80 parts of isopropyl alcohol and 420 parts of ether,
and this solution is treated with isopropanolic hydrogen chloride. The resulting
precipitate is collected by filtration and washed with acetone to afford 17β-[N-
(3-dimethylaminopropyl)formamido-1-androst-5-en-3β-ol hydrochloride. A
solution of this hydrochloride in aqueous methanol is made alkaline by the
addition of dilute aqueous sodium hydroxide, and the resulting colloidal
precipitate is extracted with chloroform. The chloroform extracts washed with
water, dried over anhydrous sodium sulfate and concentrated to dryness to
afford a residue, which is crystallized from acetone, resulting in 17β-[N-(3-
dimethylaminopropyl)formamido]androst-5-en-3β-ol, which displays a double
melting point at about 116-118°C and 143-148°C, [α]D= -67.5° (chloroform).To a slurry of 4 parts of LiAlH4 in 150 parts of dioxane is added dropwise with
stirring, at the reflux temperature a solution of 10 parts of 17β-[N-(3-
dimethylaminopropyl)
formamido]androst-5-en-3β-ol in 150 parts of dioxane. This reaction mixture
is heated at reflux for about 18 hours longer, and then treated dropwise
successively, at the reflux temperature, with a solution of 4 parts of water in
25 parts of dioxane, 3 parts of 20% aqueous sodium hydroxide, and 14 parts
of water. The resulting mixture is clarified by filtration, and the residue on the
filter is washed with fresh dioxane. The filtrates are combined, evaporated to
dryness under reduced pressure, and the resulting residue is recrystallized
from acetone-methanol to produce 17β-[N-methyl-N-(3-
dimethylaminopropyl)amino]androst-5-en-3β-ol, M.P. about 146-148°C, [α]D=
-54.5° (chloroform). A solution of this amine in ether-isopropyl alcohol is
treated with isopropanolic hydrogen chloride to afford Azacosterol
dihydrochloride, [α]D= -32° (methanol).
Therapeutic Function
Hypocholesteremic
Safety Profile
Poison by ingestion andintraperitoneal routes. Experimental reproductive effects.Mutation data reported. When heated to decomposition itemits toxic fumes of NOx and HCl.
Check Digit Verification of cas no
The CAS Registry Mumber 1249-84-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,4 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1249-84:
(6*1)+(5*2)+(4*4)+(3*9)+(2*8)+(1*4)=79
79 % 10 = 9
So 1249-84-9 is a valid CAS Registry Number.
InChI:InChI=1/C25H44N2O.2ClH/c1-24-13-11-19(28)17-18(24)7-8-20-21-9-10-23(25(21,2)14-12-22(20)24)27(5)16-6-15-26(3)4;;/h7,19-23,28H,6,8-17H2,1-5H3;2*1H/t19-,20-,21-,22-,23-,24-,25-;;/m0../s1
