17692-51-2

Basic information

• Product Name: METERGOLINE
• Synonyms: n-cbz-[(8β)-1,6-dimethylergolin-8-yl]methylamine;N-Cbz-[(8β)-1,6-Dimethylergolin-8-yl]methylamine, [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester;[((8beta)-1,6-Dimethylergoline-8-yl)methyl]carbamic acid phenylmethyl ester;Lyserdol;N-[(1,6-Dimethylergolin-8β-yl)methyl]carbamic acid benzyl ester;[(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamicacidphenylmethylester;D-[(4,6,6a,7,8,9,10,10a-Octahydro-4,7-dimethyl-10aalpha-indolo[4,3-fg]quinolin-9beta-yl)methyl]carbamic acid benzyl ester;liserdol
• CAS NO: 17692-51-2
• Molecular Formula: C₂₅H₂₉N₃O₂
• Molecular Weight: 403.52
• EINECS: 241-686-3
• Product Categories: Serotonin receptor
• Mol File: 17692-51-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 148-150 °C(lit.)
• Boiling Point: 612.5 °C at 760 mmHg
• Flash Point: 324.2 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: 0.1 M HCl: 1.4 mg/mL
• PKA: 12.45±0.46(Predicted)
• 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.
• Merck: 13,5962
• CAS DataBase Reference: METERGOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: METERGOLINE(17692-51-2)
• EPA Substance Registry System: METERGOLINE(17692-51-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: FA1070000
• Hazardous Substances Data: 17692-51-2(Hazardous Substances Data)

Usage

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.

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.

References

Aulakh et al. (1992), Effects of various serotonin receptor subtype-selective antagonists alone and on m-chlorophenylpiperazine-induced neuroendocrine changes in rats; J. Pharmacol. Exp. Ther., 263 588 Bagdy et al. (1992), Pharmacological characterization of serotonin receptor subtypes involved in vasopressin and plasma renin activity responses to serotonin agonists; Eur. J. Pharmacol., 210 285 Knight et al. (2009), Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists; Mol. Pharmacol., 75 374 Falsetti et al. (1982), Metergoline in the management of hyperprolactinemia amenorrhea and anovulation; Gynecol. Obstet. Invest., 13 108 Turner et al. (2002), Double-blind, placebo-controlled study of single-dose metergoline in depressed patients with seasonal affective disorder; J. Clin. Psychopharmacol., 22 216

InChI:InChI=1/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/p+1/t18-,21+,23+/m0/s1

Downstream Products

• 2169-46-2 N-(((6aR,9S,10aR)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl)propionamide