121588-75-8 Usage
Originator
Amesergide,Onbio Inc.
Uses
Serotonin antagonist.
Manufacturing Process
To a 250 ml three-neck round bottom flask was added 10.0 g (32.01 mmol) of
(8β)-1-isopropyl-6-methylergoline-8-carboxylie acid, 4.43 g (32.1 mmol) of
potassium carbonate and 200 ml of N,N-dimethylformamide. The mixture was
refluxed and 25 ml of a distillate was collected. The remaining solution was
cooled in an ice bath, and then with an acetonitrile/carbon dioxide bath which
lowered the temperature of the reaction mixture to about -45°C this mixture
was added 4.59 g (33.62 mmol) of isobutyl chloroformate dropwise. The
resulting mixture was stirred for approximately 5 min and 3.49 g (35.21
mmol) of cyclohexylamine was added. The reaction mixture was allowed to
warm to room temperature and stirred for approximately 19 h. To the mixture
was added 500 ml of ice water containing 25 ml of concentrated ammonium
hydroxide. The mixture was cooled and the precipitated solid was collected by
vacuum filtration. The resulting solid was washed with water and dried in
vacuo to provide 10.13 g (yield 76.8%) of the (8β)-N-cyclohexyl-1-isopropyl-
6-methylergoline-8-carboxamide having a purity of 92.3%.
The resulting solid was combined with three other lots of the desired
compound previously synthesized to provide a total weight of 33.6 g. This
material was dissolved in 1200 ml of hot methanol and the resulting solution
was filtered. The filtrate was allowed to cool to room temperature and 600 ml
of water was added dropwise. The mixture was cooled in the freezer and the
precipitated crystals were collected by vacuum filtration. The crystals were
washed with methanol and dried in vacuo to provide 26.95 g of the desired
compound having a purity of 96.5% as determined by HPLC. The dried solid
was dissolved in 1100 ml of hot methanol, and the resulting solution was
filtered hot and allowed to cool. To this mixture was added 600 ml of water
and again the precipitated solid was collected by vacuum filtration. The solid
was washed with water and dried in vacuo to provide 25.82 g of the (8β)-Ncyclohexyl-
1-isopropyl-6-methylergoline-8-carboxamide, melting point 250°C.
The assayed material indicated 98.7% purity.
Therapeutic Function
Serotonin antagonist
Check Digit Verification of cas no
The CAS Registry Mumber 121588-75-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,1,5,8 and 8 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 121588-75:
(8*1)+(7*2)+(6*1)+(5*5)+(4*8)+(3*8)+(2*7)+(1*5)=128
128 % 10 = 8
So 121588-75-8 is a valid CAS Registry Number.
InChI:InChI=1/C25H35N3O/c1-16(2)28-15-17-13-23-21(20-10-7-11-22(28)24(17)20)12-18(14-27(23)3)25(29)26-19-8-5-4-6-9-19/h7,10-11,15-16,18-19,21,23H,4-6,8-9,12-14H2,1-3H3,(H,26,29)/t18-,21?,23?/m1/s1
121588-75-8Relevant articles and documents
CYCLOALKYLAMIDES OF (8BETA)-1-ALKYL-6-(SUBSTITUTED) ERGOLINES
-
, (2008/06/13)
This invention provides (8β)-N-cycloalkyl-1-alkyl-6-(substituted) ergoline-8-carboxamides useful for blocking 5HT 2 receptors in mammals having an excess of serotonin centrally or peripherally. The invention also provides methods for treating hypertension, migraine, vasospasm, thrombosis, ischemia, depression, anxiety, sleep disorders and appetite disorders with a compound of the invention.
(8β)-6-Methylergoline amide derivatives as serotonin antagonists: N1-substituent effects on vascular 5HT2 receptor activity
Misner,Garbrecht,Marzoni,Whitten,Cohen
, p. 652 - 656 (2007/10/02)
A series of (8β)-6-methylergoline amide derivatives was synthesized with various alkyl substituents in the N1-position in order to evaluate their effectiveness in blocking vascular 5HT2 receptors. The influence of both the N1 substituent and amide derivative proved to be of great importance on binding affinities to vascular 5HT2 receptors. Within each series of amides, however, maximum affinity was achieved with an N1-isopropyl substituent (14, 18, 26, 38, and 41; all with 2.7-5.0 times greater affinity than their N1-H analogues), with the exception of two cases (22 and 37) in the cyclohexylamide derivatives wherein N1-methyl equalled the isopropyl in potency. Other than these exceptions, affinities followed the pattern of H Me Et iPr, with potencies falling off with larger alkyl substituents.
