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81409-90-7

Basic Information
CAS No.: 81409-90-7
Name: Cabergoline
Molecular Structure:
Molecular Structure of 81409-90-7 (Cabergoline)
Formula: C26H37N5O2
Molecular Weight: 451.60
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:
Flash Point:
Solubility:
Appearance: White crystalline solid
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 26-36/37
Transport Information:
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
474397-67-6

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

81409-90-7

cabergoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaHMDS / tetrahydrofuran / -40 - 20 °C
2: propan-2-ol / 18 h / 50 °C
3: aqueous hydrochloric acid / H2O / 1 h / 80 °C
View Scheme
474397-68-7

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

81409-90-7

cabergoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: propan-2-ol / 18 h / 50 °C
2: aqueous hydrochloric acid / H2O / 1 h / 80 °C
View Scheme
109-55-7

1-amino-3-(dimethylamino)propane

81409-90-7

cabergoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / acetic acid / Heating
2: 81 percent / toluene / Heating
View Scheme

C29H45N5O2Si

81409-90-7

cabergoline

Conditions
ConditionsYield
With ammonium fluoride In tetrahydrofuran; water
909724-71-6

C32H51N5O2Si

81409-90-7

cabergoline

Conditions
ConditionsYield
With ammonium fluoride In methanol; water at 20℃; for 3h;
1892-57-5

N-(3-dimethylaminopropyl)-N-ethylcarbodiimide

81409-74-7

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

81409-90-7

cabergoline

Conditions
ConditionsYield
Stage #1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid In trifluoromethylbenzene (BTF) at 24 - 38℃;
Stage #2: With water; acetic acid In trifluoromethylbenzene (BTF) pH=5.0 - 5.5;
Stage #3: With potassium hydroxide In tert-butyl methyl ether; water pH=9.5 - 10.0;

1-((6-allylergolin-8β-yl)-carbonyl)-1-(3-dimethylaminopropyl)-3-ethylurea 2-chlorotoluene solvate

81409-90-7

cabergoline

Conditions
ConditionsYield
at 30 - 60℃; under 0.750075 Torr; for 25h; Product distribution / selectivity;
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

81409-90-7

cabergoline

Conditions
ConditionsYield
Stage #1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 30h;
Stage #2: With ammonia; water In dichloromethane
994-05-8

tert-Amyl methyl ether

81409-90-7

cabergoline

Form TAME cabergoline

Conditions
ConditionsYield
Stage #1: tert-Amyl methyl ether; cabergoline at 41 - 50℃; for 0.25h;
Stage #2: cabergoline at 0 - 27℃; for 16.5h;
88.8%
123-00-2

4-(3-Aminopropyl)morpholine

81409-90-7

cabergoline

1419268-44-2

(5R,8R,10R)-6-allyl-N-[3-(morpholino)propyl]ergoline-8-carboxamide

Conditions
ConditionsYield
at 65℃; for 144h; Inert atmosphere; Sealed tube;80%
at 65℃; for 144h; Inert atmosphere; Sealed tube;80%
81409-90-7

cabergoline

108-90-7

chlorobenzene

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

Conditions
ConditionsYield
In n-heptane at -20 - 20℃; for 1.25h;
142-82-5

n-heptane

100-41-4

ethylbenzene

81409-90-7

cabergoline

Cabergoline ethylbenzene/n-heptane

Conditions
ConditionsYield
Stage #1: ethylbenzene; cabergoline at -23 - 30℃; for 0.5h;
Stage #2: n-heptane at -23 - -17℃; for 3.66667h;
67-56-1

methanol

81409-90-7

cabergoline

72821-79-5

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

Conditions
ConditionsYield
With triethylamine
81409-90-7

cabergoline

1419268-43-1

(5R,8R,10R)-6-allyl-N-[3-(morpholino)propyl]-N-[(ethylamino)carbonyl]-ergoline-8-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; methanol
2: triethylamine / dichloromethane
View Scheme
Multi-step reaction with 3 steps
1: 144 h / 65 °C / Inert atmosphere; Sealed tube
2: dmap / tetrahydrofuran
3: isopropyl alcohol / 50 °C
View Scheme
81409-90-7

cabergoline

81409-74-7

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

Conditions
ConditionsYield
Stage #1: cabergoline With sodium hydroxide In methanol; water
Stage #2: With hydrogenchloride In methanol; water
81409-90-7

cabergoline

C37H46N4O6

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 144 h / 65 °C / Inert atmosphere; Sealed tube
2: dmap / tetrahydrofuran
View Scheme
887144-97-0

Togni's reagent

81409-90-7

cabergoline

1515864-84-2

C27H36F3N5O2

Conditions
ConditionsYield
With copper (I) acetate In methanol at 40℃; for 4.5h; Inert atmosphere;
81409-90-7

cabergoline

7585-39-9

β‐cyclodextrin

C26H37N5O2*C42H70O35

Conditions
ConditionsYield
Stage #1: cabergoline; β‐cyclodextrin In methanol; water at 20℃; for 0.5h; Sonication;
Stage #2: In methanol; water at 20 - 50℃; for 48h;
81409-90-7

cabergoline

L-theanine cabergoline cocrystal

Conditions
ConditionsYield
In water; isopropyl alcohol
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  • Cabergoline CAS NO.81409-90-7

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    81409-90-7

    Cabergoline CAS NO.81409-90-7

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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.