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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
EC Number:
241-686-3
MDL number:
MFCD00153829
UNSPSC Code:
12352200
PubChem Substance ID:
24278105
NACRES:
NA.77

Quality Level

100

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)

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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-HT1A receptor binding assays

Biochem/physiol Actions

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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

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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
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
N J Beijerink et al.
Reproduction (Cambridge, England), 128(2), 181-188 (2004-07-29)
Dopamine agonists decrease plasma prolactin concentration and shorten the duration of anoestrus in the bitch. In order to determine whether this shortening results from decreased prolactin release or is due to another dopamine agonistic effect on the pulsatile release of
B K Smith et al.
The American journal of physiology, 277(3 Pt 2), R802-R811 (1999-09-14)
Systemic treatment with dexfenfluramine (dF), fluoxetine, or serotonin (5-hydroxytryptamine, 5-HT) recently was shown to suppress fat and occasionally protein but not carbohydrate intake in rats when a macronutrient selection paradigm was employed. These reports contrast with the prevailing literature, which
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