M3668

Metergoline

• Synonyme(s) : N-CBZ-[(8β)-1,6-Dimethylergolin-8-yl]methylamine, [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
• Formule empirique (notation de Hill): C₂₅H₂₉N₃O₂
• Numéro CAS: 17692-51-2
• Poids moléculaire : 403.52
• Numéro CE : 241-686-3
• Numéro MDL: MFCD00153829
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278105
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 100
• Pf: 148-150 °C (lit.)
• Solubilité: 0.1 M HCl: 1.4 mg/mL; ethanol: 4 mg/mL; H₂O: insoluble
• Température de stockage: −20°C
• Chaîne SMILES: [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
• Clé InChI: WZHJKEUHNJHDLS-QTGUNEKASA-N
• Informations sur le gène: 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

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H302 + H312 + H332
• Conseils de prudence: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312
• Classification des risques: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Faceshields, Gloves