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M3668

Sigma-Aldrich

Metergoline

Sinónimos:

N-CBZ-[(8β)-1,6-Dimethylergolin-8-yl]methylamine, [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester

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About This Item

Fórmula empírica (notación de Hill):
C25H29N3O2
Número de CAS:
17692-51-2
Peso molecular:
403.52
Número CE:
241-686-3
Número MDL:
MFCD00153829
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24278105
NACRES:
NA.77

Nivel de calidad

100

mp

148-150 °C (lit.)

solubilidad

0.1 M HCl: 1.4 mg/mL
ethanol: 4 mg/mL
H2O: insoluble

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

WZHJKEUHNJHDLS-QTGUNEKASA-N

Información sobre el gen

human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR7(3363)
rat ... Htr7(65032)

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Aplicación

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-HT1A receptor binding assays

Acciones bioquímicas o fisiológicas

Metergoline is an ergot alkaloid and a selective serotonin antagonist which blocks the 5-HT2A and 5-HT2C 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.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302 + H312 + H332

Clasificaciones de peligro

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificados de análisis (COA)

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K Stachowicz et al.
Neuropharmacology, 53(6), 741-748 (2007-09-18)
The purpose of the present study was to investigate whether the anxiolytic-like action of a selective and brain penetrable group I metabotropic glutamate (mGlu5) receptor antagonist 3-[(2-methyl-1,3-tiazol-4-yl)ethynyl]-pyridine (MTEP) is dependent upon the serotonergic system. Experiments were performed on male Wistar
Camila Marroni Roncon et al.
Planta medica, 77(3), 236-241 (2010-09-17)
The objective of this study was to investigate the effects of chronic administration of a semi-purified extract (Purified Extract A--PEA; 4, 8, or 16 mg/kg) of PAULLINIA CUPANA (guaraná) seeds on rats submitted to the elevated T-maze (ETM) model of
J David Glass et al.
The European journal of neuroscience, 31(6), 1117-1126 (2010-04-10)
Timing of the circadian clock of the suprachiasmatic nucleus (SCN) is regulated by photic and non-photic inputs. Of these, neuropeptide Y (NPY) signaling from the intergeniculate leaflet (IGL) to the SCN plays a prominent role. Although NPY is critical to
Kai Kang et al.
Fungal biology, 115(3), 302-309 (2011-03-01)
Metergoline possesses potent antifungal activity against Candida krusei, a notorious yeast species that is inherently resistant to the common antifungal agents. In an attempt to elucidate the action mechanisms of metergoline, the present study was designed to investigate its effects
Boeun Lee et al.
Molecules (Basel, Switzerland), 26(11) (2021-06-03)
N-phenylpiperazine analogs can bind selectively to the D3 versus the D2 dopamine receptor subtype despite the fact that these two D2-like dopamine receptor subtypes exhibit substantial amino acid sequence homology. The binding for a number of these receptor subtype selective
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