M3668

Metergoline

• Synonym(s): N-CBZ-[(8β)-1,6-Dimethylergolin-8-yl]methylamine, [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
• Empirical Formula (Hill Notation): C₂₅H₂₉N₃O₂
• CAS Number: 17692-51-2
• Molecular Weight: 403.52
• EC Number: 241-686-3
• MDL number: MFCD00153829
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278105
• NACRES: NA.77

Properties

• mp: 148-150 °C (lit.)
• solubility: 0.1 M HCl: 1.4 mg/mL; ethanol: 4 mg/mL; H₂O: insoluble
• storage temp.: −20°C
• SMILES string: [H][C@]2(CNC(=O)OCc1ccccc1)CN(C)[C@]3([H])Cc4cn(C)c5cccc(c45)[C@@]3([H])C2
• InChI: 1S/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)/t18-,21+,23+/m0/s1
• InChI key: WZHJKEUHNJHDLS-QTGUNEKASA-N
• Gene Information: human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR7(3363) ; rat ... Htr7(65032)

Description

Application

Metergoline has been used as a serotonin receptor antagonist:

• to study its effects on astrocyte calcium signals evoked by whisker stimulation
• to study its effects on lipopolysaccharide-induced anorexia in rats
• to evaluate the non-specific binding by 5-HT_1A receptor binding assays

Biochem/physiol Actions

Metergoline is an ergot alkaloid and a selective serotonin antagonist which blocks the 5-HT_2A and 5-HT_2C receptors with higher affinity. It possesses antifungal activity against infection caused by Candida krusei. Metergoline exhibits a therapeutic effect against premenstrual dysphoric disorder. It also exhibits antipyretic and analgesic activities.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332
• Precautionary Statements: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves