Name: Cabergoline
SKU: 81409-90-7

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Basic Information

Molecular Structure:
CAS No.:	81409-90-7
Name:	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
Appearance:	White crystalline solid
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36/37
PSA:	71.68000
LogP:	3.52270

Synthetic route

: 153415-36-2
6-Norcabergoline

: 591-87-7
Allyl acetate

: 81409-90-7
cabergoline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In toluene Heating;	A 81% B 0.57 g

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Raw Materials

109-55-7

109-90-0

591-87-7

25952-53-8

Total:168 Page 1 of 5 1 2 3 4 5 Next>>

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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.

81409-90-7

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Chemistry

History

Toxicity Data With Reference

Specification