CAS No.25614-03-3,Bromocriptine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	25614-03-3
Name:	Bromocriptine
Article Data:	9

Formula:	C32H40 Br N5 O5
Molecular Weight:	654.604
Synonyms:	Ergocryptine,2-bromo- (8CI); 8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine,ergotaman-3',6',18-trione deriv.; Indolo[4,3-fg]quinoline,ergotaman-3',6',18-trione deriv.; (+)-Bromocriptine; 2-Bromo-a-ergocryptine; 2-Bromo-a-ergokryptine;2-Bromoergocriptine; 2-Bromoergocryptine; Bromergocryptine; Bromocriptin;Bromocriptine; Bromocryptine; Bromoergocryptine; Ergolactin; SAN 15-754; Sandoz15-754; a-Bromocryptine; a-Bromoergocryptine; a-Ergolactin
EINECS:	247-128-5
Density:	1.52 g/cm³
Melting Point:	215-218° (dec)
Boiling Point:	891.3 °C at 760 mmHg
Flash Point:	492.8 °C
Solubility:	2.07mg/L(temperature not stated)
Appearance:	white crystalline powder
Hazard Symbols:	Xn,Xi
Risk Codes:	R20/21/22
Safety:	Poison by intravenous and possibly other routes. Human teratogenic effects by an unspecified route: developmental abnormalities of the respiratory system, musculoskeletal system, urogenital system, craniofacial area and body wall. Human systemic effects by ingestion including: olfaction changes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes such as Br⁻ and NO_x.
PSA:	118.21000
LogP:	3.39740

Synthetic route

: 511-09-1
α-ergocryptine

: 25614-03-3
Bromocriptine

Conditions

Conditions	Yield
With bromodimethylsulfoxonium bromide In dimethyl sulfoxide for 0.166667h; Ambient temperature;	93%
With pyridazinium bromide; 3-bromo-6-chloro-2-methylimidazo In dichloromethane for 0.0333333h; Ambient temperature;	75%
With ammonium hydroxide; sodium hydroxide In dichloromethane; di-isopropyl ether; water; hydrogen bromide; dimethyl sulfoxide

: 511-09-1
α-ergocryptine

A: (6aR,9R)-5a-Hydroxy-7-methyl-5-oxo-4,5,5a,6,6a,7,8,9-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide

B: 25614-03-3
Bromocriptine

Conditions

Conditions	Yield
With water; hydrogen bromide In dimethyl sulfoxide for 0.333333h; Product distribution; Ambient temperature; halogenation of indole alkaloids with various halogenated agents;	A 8% B 72%

: 2857-97-8
trimethylsilyl bromide

: 511-09-1
α-ergocryptine

: 25614-03-3
Bromocriptine

Conditions

Conditions	Yield
With ammonium hydroxide; sodium chloride In ice-water; dichloromethane; di-isopropyl ether; dimethyl sulfoxide; ethyl acetate

: α-ergocryptine phosphate

α-ergocryptinine base: α-ergocryptinine base

: 2857-97-8
trimethylsilyl bromide

: 511-09-1
α-ergocryptine

: 25614-03-3
Bromocriptine

Conditions

Conditions	Yield
	4.7 g (0.007243 mole, 85%)
	4.7 g (0.007243 mole, 85%)

...Expand

α-ergocryptinine base: α-ergocryptinine base

: 2857-97-8
trimethylsilyl bromide

: 511-09-1
α-ergocryptine

: 25614-03-3
Bromocriptine

Conditions

Conditions	Yield
With ammonium hydroxide; sodium chloride In ice-water; dimethyl sulfoxide; ethyl acetate	mole, 87%)
With ammonium hydroxide; sodium chloride In ice-water; dimethyl sulfoxide; ethyl acetate	6.3 g (0.00967 mole, 87%)

...Expand

: α-ergocryptine phosphate

: 2857-97-8
trimethylsilyl bromide

: 25614-03-3
Bromocriptine

Conditions

Conditions	Yield
	0.9 g (0.001359 mole, 91.5%)
	0.9 g (0.001359 mole, 91.5%)

diispropyl ether: diispropyl ether

: 2857-97-8
trimethylsilyl bromide

: 511-09-1
α-ergocryptine

: 25614-03-3
Bromocriptine

Conditions

Conditions	Yield
With ammonium hydroxide; sodium chloride In ice-water; dichloromethane; dimethyl sulfoxide; ethyl acetate

...Expand

: 25614-03-3
Bromocriptine

: Bromocriptinmesilat

Conditions

Conditions	Yield
In butanone

: 3081-61-6, 5822-62-8, 17010-37-6, 34271-54-0
N-ethyl-L-glutamine

: 25614-03-3
Bromocriptine

: L-theanine bromocriptine cocrystal

Conditions

Conditions	Yield
In water; isopropyl alcohol

: 75-75-2
methanesulfonic acid

: 25614-03-3
Bromocriptine

: 22260-51-1
Cycloset

Conditions

Conditions	Yield
In methanol; water at 4℃; for 2.58333h; Solvent;

Raw Materials

511-09-1

2857-97-8

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Chemistry

Molecular Formula: C₃₂H₄₀BrN₅O₅
Molar mass: 654.59 g/mol
EINECS: 247-128-5
Density: 1.23 g/cm³
Flash Point: 201.2 °C
Index of Refraction: 1.562
Boiling Point: 608.7 °C at 760 mmHg
Vapour Pressure: 2.34E-17 mmHg at 25°C
Appearance: A white crystalline powder
Product categories of Bromocriptine (25614-03-3): Organics
Structure of Bromocriptine (25614-03-3):

XLogP3-AA: 3.8
H-Bond Donor: 3
H-Bond Acceptor: 6
SMILES: Brc2nc1cccc\3c1c2C[C@@H]7C/3=C/[C@@H](C(=O)N[C@@]4(O[C@]6(O)N(C4=O)[C@H](C(=O)N5CCC[C@H]56)CC(C)C)C(C)C)CN7C
InChI: InChI=1/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1
InChIKey: OZVBMTJYIDMWIL-AYFBDAFIBH
Std. InChI: InChI=1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1
Std. InChIKey: OZVBMTJYIDMWIL-AYFBDAFISA-N

Uses

Bromocriptine (25614-03-3) is an ergoline derivative and is a dopamine agonist that is used in the treatment of Parkinson's disease (PD), pituitary tumors, and neuroleptic malignant syndrome.Galactorrhea, female infertility, amenorrhea, hypogonadism, and acromegaly (caused by pituitary problems, such as hyperprolactinaemia) may be treated by this drug.

Production

Bromocriptine (25614-03-3) can be obtained by the reaction of Ergocryptine and N-bromo-succinic acid imide .

Toxicity Data With Reference

1.	oms-hmn:lym 100 µmol/L	MUREAV Mutation Research. 117 (1983),163.
2.	dna-rat-ipr 4 mg/kg	CNREA8 Cancer Research. 36 (1976),2223.
3.	orl-rat TDLo:7 g/kg/2Y-C:ETA,REP	BMJOAE British Medical Journal. 2 (1977),1605.
4.	orl-wmn TDLo:6 mg/kg/60D-I:NOSE	NEJMAG New England Journal of Medicine. 306 (1982),178.
5.	ivn-rat LD50:72 mg/kg	DRUGAY Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. 17 (1978),313.
6.	ivn-rbt LD50:12 mg/kg	USXXAM United States Patent Document. (Commissioner of Patents and Trademarks, Washington, DC 20231) #3752814 .
7.	unr-mus LD50:200 mg/kg	BBIADT Biomedica Biochimica Acta. 43 (1984),1305.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Poison by intravenous and possibly other routes. Human teratogenic effects by an unspecified route: developmental abnormalities of the respiratory system, musculoskeletal system, urogenital system, craniofacial area and body wall. Human systemic effects by ingestion including: olfaction changes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes such as Br⁻ and NO_x.

Specification

Bromocriptine (25614-03-3) also can be called Parlodel ; Bromocriptin ; 2-Bromoergocryptine ; (5'a)-2-Bromo-12'-hydroxy-2'-(-1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione ; Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)- and Bromocryptin .Its use has been associated with causing or worsening psychotic symptoms: its mechanism is in opposition of most antipsychotics, whose mechanisms generally block dopamine.