METERGOLINE
- Product Name
- METERGOLINE
- CAS No.
- 17692-51-2
- Chemical Name
- METERGOLINE
- Synonyms
- mce;ahr3009;Lyserdol;liserdol;metergolin;metergolina;METERGOLINE;methergoline;METERGOLINE, INTERNAL;METERGOLINE USP/EP/BP
- CBNumber
- CB1248755
- Molecular Formula
- C25H29N3O2
- Formula Weight
- 403.52
- MOL File
- 17692-51-2.mol
METERGOLINE Property
- Melting point:
- 148-150 °C(lit.)
- alpha
- D28 -7 ±2°
- Boiling point:
- 612.5±55.0 °C(Predicted)
- Density
- 1.25±0.1 g/cm3(Predicted)
- storage temp.
- −20°C
- solubility
- 0.1 M HCl: 1.4 mg/mL
- pka
- 12.45±0.46(Predicted)
- form
- solid
- color
- White
- Merck
- 13,5962
- Stability:
- Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethaqnol may be stored at -20°C for up to 2 month.
- InChIKey
- WZHJKEUHNJHDLS-QTGUNEKASA-N
- CAS DataBase Reference
- 17692-51-2(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
N-Bromosuccinimide Price
- Product number
- M3668
- Product name
- Metergoline
- Packaging
- 500mg
- Price
- $164
- Updated
- 2025/07/31
- Product number
- M3668
- Product name
- Metergoline
- Packaging
- 5g
- Price
- $1530
- Updated
- 2025/07/31
- Product number
- 21336
- Product name
- Metergoline
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 21336
- Product name
- Metergoline
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $70
- Updated
- 2024/03/01
- Product number
- 21336
- Product name
- Metergoline
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $116
- Updated
- 2024/03/01
METERGOLINE Chemical Properties,Usage,Production
Description
Metergoline (17692-51-2) is an ergot alkaloid derivative acting as antagonist at serotonin 5HT1 and 5HT2 receptors1,2 and 5HT7 receptors3. A safe and effective agent for management of hyperprolactinemic amenorrhea and anovulation.4 Displays a long-lasting antidepressant effect in seasonal affective disorder.5
Chemical Properties
White Solid
Originator
Liserdol,Farmitalia,Italy,1970
Uses
Metergoline is an antagonist at 5-HT1, 5-HT2, and 5-HT7 serotonin receptors. Metergoline is an analgesic; antipyretic.
Definition
ChEBI: Metergoline is an ergoline alkaloid that is the N-benzyloxycarbonyl derivative of lysergamine. A 5-HT2 antagonist. Also 5-HT1 antagonist and 5-HT1D ligand. Has moderate affinity for 5-HT6 and high affinity for 5-HT7. It has a role as a serotonergic antagonist, a dopamine agonist and a geroprotector. It is an ergoline alkaloid and a carbamate ester.
Manufacturing Process
16 g of 1-methyl-dihydro-lysergamine (the 10-position hydrogen has the αconfiguration) are dissolved in 80 cc of anhydrous pyridine by mildly heating. To the solution, cooled to -10°C and stirred, 18 cc of 85% carbobenzoxychloride (in toluene) diluted in 36 cc of chloroform are added dropwise, rather rapidly. The mixture is kept at -10°C during the addition, and for 10 minutes afterwards. The cooling means is removed and the temperature is allowed to rise to room level in 10 minutes. The reaction mixture is diluted with 240 cc of chloroform and rapidly washed with 80 cc of 5% aqueous sodium hydroxide solution, with saturated aqueous sodium bicarbonate solution, and finally with water.
The chloroform solution is briefly dried over anhydrous sodium sulfate and evaporated to dryness in vacuo at 40°C. The oily residue is taken up in 160 cc of benzene and passed through a column containing 48 g of alumina. The column is then eluted with further 160 cc of benzene. The collected eluates are evaporated in vacuo at 40°C. The thick oily residue is mixed with a small amount of anhydrous diethyl ether. After some time a crystalline mass is obtained, which is collected and washed with a small amount of benzene and diethyl ether. 12 g of white crystals are obtained, melting at 146° to 148°C.
Therapeutic Function
Analgesic
Biological Activity
Antagonist at 5-HT 1 /5-HT 2 with activity at 5-HT 1D . Has moderate affinity for 5-HT 6 and high affinity for 5-HT 7 .
Biochem/physiol Actions
Antagonist at 5-HT1, 5-HT2, and 5-HT7 serotonin receptors; analgesic; antipyretic.
storage
Room temperature
References
[1] C S AULAKH D L M J L Hill. Effects of various serotonin receptor subtype-selective antagonists alone and on m-chlorophenylpiperazine-induced neuroendocrine changes in rats.[J]. Journal of Pharmacology and Experimental Therapeutics, 1992, 263 2: 588-595.
[2] GYORGY BAGDY . Pharmacological characterization of serotonin receptor subtypes involved in vasopressin and plasma renin activity responses to serotonin agonists[J]. European journal of pharmacology, 1992, 210 3: Pages 285-289. DOI:10.1016/0014-2999(92)90417-3
[3] JESSICA A KNIGHT. Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists.[J]. Molecular Pharmacology, 2009, 75 2: 374-380. DOI:10.1124/mol.108.052084
[4] L FALSETTI. Metergoline in the management of hyperprolactinemic amenorrhea and anovulation.[J]. Gynecologic and Obstetric Investigation, 1982, 13 2: 108-116. DOI:10.1159/000299491
[5] E. TURNER. Double-Blind, Placebo-Controlled Study of Single-Dose Metergoline in Depressed Patients With Seasonal Affective Disorder[J]. Journal of Clinical Psychopharmacology, 2002, 22 1: 216-220. DOI:10.1097/00004714-200204000-00018
METERGOLINE Preparation Products And Raw materials
Raw materials
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View Lastest Price from METERGOLINE manufacturers
- Product
- METERGOLINE 17692-51-2
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-08-11