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81409-90-7

Basic Information
CAS No.: 81409-90-7
Name: Cabergoline
Article Data: 12
Cas Database
Molecular Structure:
Molecular Structure of 81409-90-7 (Cabergoline)
Formula: C26H37N5O2
Molecular Weight: 451.612
Synonyms: Ergoline-8-carboxamide,N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)-, (8b)- (9CI);Cabaser;Cabaseril;1-((6-Allylergolin-8beta-yl)carbonyl)-1-(3-(dimethylamino)propyl)-3-ethylurea;Ergoline-8beta-carboxamide, N-(3-(dimethylamino)propyl)-N-((ethylamino)carbonyl)-6-(2-propenyl)-;
EINECS: 200-419-0
Density: 1.156 g/cm3
Melting Point: 102-104°C
Boiling Point: N/A
Flash Point: N/A
Solubility: N/A
Appearance: White crystalline solid
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 26-36/37
Transport Information: N/A
PSA: 71.68000
LogP: 3.52270
Synthetic route
153415-36-2

6-Norcabergoline

591-87-7

Allyl acetate

81409-90-7

cabergoline

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 2h;92.3%

1-((6-allylergolin-8β-yl)-carbonyl)-1-(3-dimethylaminopropyl)-3-ethylurea chlorobenzene solvate

81409-90-7

cabergoline

Conditions
ConditionsYield
In n-heptane at 55℃; Product distribution / selectivity;90%
at 55 - 70℃; under 1.50015 Torr; for 24 - 92h; Product distribution / selectivity;
at 60℃; under 750.075 Torr; for 24h;
In diethyl ether; n-heptane at -35 - -15℃; for 8h; Product distribution / selectivity;

Cabergoline ethylbenzene/n-heptane

81409-90-7

cabergoline

Conditions
ConditionsYield
for 15h; Product distribution / selectivity; Drying under a blanket of nitrogen;86%
at 40℃; under 65.2565 - 83.2583 Torr; for 16 - 17h; Product distribution / selectivity;
at 60℃; for 20.5h; Product distribution / selectivity;
at 20 - 25℃; under 525.053 - 675.068 Torr; for 29.25h; Product distribution / selectivity; Vacuum;
at 40℃; for 2h; Product distribution / selectivity; Stream of nitrogen;
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

109-90-0

ethyl isocyanate

A

81409-90-7

cabergoline

B

126554-50-5

(6aR,9R,10aR)-7-allyl-N9-[3-(dimethylamino)propyl]-N4-ethyl-N9-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide

Conditions
ConditionsYield
In toluene Heating;A 81%
B 0.57 g
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

109-90-0

ethyl isocyanate

81409-90-7

cabergoline

Conditions
ConditionsYield
Stage #1: (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at -2 - 18℃; for 14h;
Stage #2: ethyl isocyanate In dichloromethane at 18℃; for 48h;
Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at -2℃; for 4h;
68.2%
25952-53-8

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

81409-74-7

(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid

A

81409-90-7

cabergoline

B

81409-91-8

N-<<<3-(dimethylamino)propyl>amino>carbonyl>-N-ethyl-6-(2-propenyl)-ergoline-8β-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 20h; Product distribution / selectivity;A 54.7%
B n/a
With triethylamine In N,N-dimethyl-formamide Ambient temperature;A 46%
B 35%
With triethylamine In ethyl acetate at 20℃; Product distribution / selectivity;
474397-69-8

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate

81409-90-7

cabergoline

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 1h;
72821-79-5

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

81409-90-7

cabergoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 85 percent / 2-hydroxypyridine / ethane-1,2-diol / 18 h / 100 °C
2: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C
3: NaHMDS / tetrahydrofuran / -40 - 20 °C
4: propan-2-ol / 18 h / 50 °C
5: aqueous hydrochloric acid / H2O / 1 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / acetic acid / Heating
2: 81 percent / toluene / Heating
View Scheme
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

81409-90-7

cabergoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C
2: NaHMDS / tetrahydrofuran / -40 - 20 °C
3: propan-2-ol / 18 h / 50 °C
4: aqueous hydrochloric acid / H2O / 1 h / 80 °C
View Scheme
109-55-7

1-amino-3-(dimethylamino)propane

Boc-β-alanine-(4-carbonylaminomethyl)benzyl ester copoly(styrene-divinylbenzene)resin

Boc-β-alanine-(4-carbonylaminomethyl)benzyl ester copoly(styrene-divinylbenzene)resin

81409-90-7

cabergoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 85 percent / 2-hydroxypyridine / ethane-1,2-diol / 18 h / 100 °C
2: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C
3: NaHMDS / tetrahydrofuran / -40 - 20 °C
4: propan-2-ol / 18 h / 50 °C
5: aqueous hydrochloric acid / H2O / 1 h / 80 °C
View Scheme
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Chemistry

Molecular Structure of Cabergoline (CAS NO.81409-90-7):

Molecular Formula: C26H37N5O2
Formula Weight: 451.6
H bond acceptors: 7
H bond donors: 2
Freely Rotating Bonds: 8
Polar Surface Area: 71.68 Å2
Index of Refraction: 1.594
Molar Refractivity: 132.54 cm3
Molar Volume: 390.4 cm3
Surface Tension: 48.6 dyne/cm
Density: 1.156 g/cm3
Melting point: 102-104°C
InChI
InChI=1/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1
Smiles
c12[C@@H]3[C@H]([N@@](C[C@@H](C3)C(N(C(NCC)=O)CCCN(C)C)=O)CC=C)Cc3c1c([nH]c3)ccc2
Product Categories: Intermediates & Fine Chemicals; Neurochemicals; Pharmaceuticals

History

 Cabergoline was invented by scientists working for the Italian drug company Farmitalia-Carlo Erba SpA in Milan in 1981/82, who were experimenting with semisynthetic derivatives of the ergot alkaloids. Farmitalia-Carlo Erba was acquired by Pharmacia in 1992, which in turn was acquired by Pfizer in 2002. The drug was not FDA approved until 2002. It went generic in late 2005 following US patent expiration.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 400mg/kg (400mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 24, Pg. 421, 1989.

Specification

  Cabergoline , with CAS number of 81409-90-7, can be called Ergoline-8-carboxamide,N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)-, (8b)- (9CI) ; Cabaser ; Cabaseril ; 1-((6-Allylergolin-8beta-yl)carbonyl)-1-(3-(dimethylamino)propyl)-3-ethylurea ; Ergoline-8beta-carboxamide, N-(3-(dimethylamino)propyl)-N-((ethylamino)carbonyl)-6-(2-propenyl)- . It is a white crystalline solid, used as a dopamine D2-receptor agonist. It is frequently used as a second-line agent in the management of prolactinomas when bromocriptine is ineffective.