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25614-03-3

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25614-03-3 Usage

Chemical Properties

Crystals.

Uses

Different sources of media describe the Uses of 25614-03-3 differently. You can refer to the following data:
1. Bromocriptine, a dopaminomimetic that is a dopamine D2 receptor agonist, possesses expressed antiparkinsonian activity. It is used for treating all phases of idiopathic and postencephalic Parkinsonism.
2. Enzyme inhibitor (prolactin).

Definition

An semisynthetic ergotamine alkaloid derivative and powerful dopamine D2 agonist. It inhibits prolactin secretion and release from the pituitary and retards tumor growth.

Brand name

Parlodel (Novartis);Bromed;Lactismine;Parilac;Umprel.

World Health Organization (WHO)

Bromocriptine, a semisynthetic ergot alkaloid derivative and prolactin inhibitor was introduced into medicine in 1976. It is used in the prevention of lactation, but because of the risk of rebound effect and since only 10% of women benefit therapeutically from such intervention, the United States Food and Drug Administration has requested manufacturers to no longer indicate preparations containing bromocriptine for this purpose. The World Health Organization is not aware of similar action having been taken elsewhere.

Hazard

Poison; teratogen; developmental abnor- malities of the respiratory system,musculoskeletal system, rogenital system, craniofacial area, and body wall; teratogen; mutagen; questionable car- cinogen; tumorigen; causes nausea, vomiting, orthostatic hypotension; constipation, dyskinesias, psychoses, digital spasm, erythromelalgia.

Mechanism of action

Bromocriptine is absorbed after oral administration, but approximately 90% of a dose undergoes extensive first-pass hepatic metabolism, with the remainder hydrolyzed in the liver to inactive metabolites that are eliminated mostly in the bile. The half-life is relatively short (~3 hours).

Clinical Use

Bromocriptine is an ergot peptide derivative that is a partial agonist at D1-type and a full agonist at D2-type postsynaptic dopamine receptors, usually given in combination with levodopa therapy. It was the first direct dopamine receptor agonist used in treatment of Parkinson's disease after its development as an inhibitor of prolactin release (via activation of anterior pituitary D2 receptors). At low doses (typically 1–5 mg/day), bromocriptine is an effective prolactin inhibitor, and at higher doses (typically 10–20 mg/day), the antiparkinsonism and mood-elevating effects of bromocriptine become apparent.

Side effects

Bromocriptine has a number of undesirable side effects, even causing mental disturbances in long-term use.

Synthesis

Bromocriptine, 2-bromoergocriptine (10.1.13), is a semisynthetic derivative of a natural ergot alkaloid, ergocriptin (a derivative of lysergic acid), which is synthesized by bromination of ergocriptin using N-bromosuccinimide [18,19].

Drug interactions

Potentially hazardous interactions with other drugs Increased risk of toxicity with bromocriptine and isometheptene.

Metabolism

Bromocriptine is extensively metabolised. It undergoes extensive first-pass biotransformation in the liver, reflected by complex metabolite profiles and by almost complete absence of parent drug in urine and faeces. In plasma the elimination half life is 3-4 hours for the parent drug and 50 hours for the inactive metabolites.The parent drug and its metabolites are also completely excreted via the liver with only 6% being eliminated via the kidney.

Check Digit Verification of cas no

The CAS Registry Mumber 25614-03-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,6,1 and 4 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 25614-03:
(7*2)+(6*5)+(5*6)+(4*1)+(3*4)+(2*0)+(1*3)=93
93 % 10 = 3
So 25614-03-3 is a valid CAS Registry Number.

25614-03-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name bromocriptine

1.2 Other means of identification

Product number -
Other names Bromoergocryptine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:25614-03-3 SDS

25614-03-3Synthetic route

α-ergocryptine
511-09-1

α-ergocryptine

Bromocriptine
25614-03-3

Bromocriptine

Conditions
ConditionsYield
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
α-ergocryptine
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

(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

Bromocriptine
25614-03-3

Bromocriptine

Conditions
ConditionsYield
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%
trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

α-ergocryptine
511-09-1

α-ergocryptine

Bromocriptine
25614-03-3

Bromocriptine

Conditions
ConditionsYield
With ammonium hydroxide; sodium chloride In ice-water; dichloromethane; di-isopropyl ether; dimethyl sulfoxide; ethyl acetate
α-ergocryptine phosphate

α-ergocryptine phosphate

α-ergocryptinine base

α-ergocryptinine base

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

α-ergocryptine
511-09-1

α-ergocryptine

Bromocriptine
25614-03-3

Bromocriptine

Conditions
ConditionsYield
4.7 g (0.007243 mole, 85%)
4.7 g (0.007243 mole, 85%)
α-ergocryptinine base

α-ergocryptinine base

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

α-ergocryptine
511-09-1

α-ergocryptine

Bromocriptine
25614-03-3

Bromocriptine

Conditions
ConditionsYield
With ammonium hydroxide; sodium chloride In ice-water; dimethyl sulfoxide; ethyl acetatemole, 87%)
With ammonium hydroxide; sodium chloride In ice-water; dimethyl sulfoxide; ethyl acetate6.3 g (0.00967 mole, 87%)
α-ergocryptine phosphate

α-ergocryptine phosphate

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

Bromocriptine
25614-03-3

Bromocriptine

Conditions
ConditionsYield
0.9 g (0.001359 mole, 91.5%)
0.9 g (0.001359 mole, 91.5%)
diispropyl ether

diispropyl ether

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

α-ergocryptine
511-09-1

α-ergocryptine

Bromocriptine
25614-03-3

Bromocriptine

Conditions
ConditionsYield
With ammonium hydroxide; sodium chloride In ice-water; dichloromethane; dimethyl sulfoxide; ethyl acetate
Bromocriptine
25614-03-3

Bromocriptine

Bromocriptinmesilat

Bromocriptinmesilat

Conditions
ConditionsYield
In butanone
Bromocriptine
25614-03-3

Bromocriptine

L-theanine bromocriptine cocrystal

L-theanine bromocriptine cocrystal

Conditions
ConditionsYield
In water; isopropyl alcohol
methanesulfonic acid
75-75-2

methanesulfonic acid

Bromocriptine
25614-03-3

Bromocriptine

Cycloset
22260-51-1

Cycloset

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

25614-03-3Downstream Products

25614-03-3Relevant articles and documents

SIDE REACTIONS IN BROMINATION OF α-ERGOCRYPTINE

Cvak, Ladislav,Stuchlik, Josef,Schreiberova, Magdalena,Sedmera, Petr,Flieger, Miroslav

, p. 565 - 572 (2007/10/02)

2,3-Dihydro-2-oxo-α-ergocryptine (III) and 2,3-dihydro-2-oxo-3-hydroxy-α-ergocryptine (IV) were found as the side reaction products in bromination of α-ergocryptine (I) with bromine in the presence of water. 2,3-Dihydro-2-oxo-3-ethoxy-α-ergocryptine (V) was formed in the presence of ethanol.

Process for the preparation of 2-halogenated ergoline derivatives

-

, (2008/06/13)

The invention relates to a novel process for the halogenation in 2-position of ergot alkaloids. The process is characterized by that as a halogenating agent a system consisting of dimethylsulfoxide, a trialkylhalosilane or triarylhalosilane and optionally a hydrogen halide is used.

Process for the preparation of 2-halogenated ergoline derivatives

-

, (2008/06/13)

The invention relates to a novel process for the halogenation in 2-position of ergot alkaloids. The process is characterized by that as a halogenating agent a system consisting of dimethylsulfoxide, a trialkylhalosilane or triaryl-halosilane and optionally a hydrogen halide is used.

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