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M3668

Sigma-Aldrich

Metergolin

Synonym(e):

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

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500 MG
€ 157,00
5 G
€ 1.430,00

About This Item

Empirische Formel (Hill-System):
C25H29N3O2
CAS-Nummer:
17692-51-2
Molekulargewicht:
403.52
EG-Nummer:
241-686-3
MDL-Nummer:
MFCD00153829
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278105
NACRES:
NA.77

€ 157,00

Voraussichtliches Versanddatum31. Mai 2025

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mp (Schmelzpunkt)

148-150 °C (lit.)

Löslichkeit

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

Lagertemp.

−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

InChIKey

WZHJKEUHNJHDLS-QTGUNEKASA-N

Angaben zum 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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Anwendung

Metergoline has been used as a serotonin receptor antagonist:

  • to study its effects on astrocyte calcium signals evoked by whisker stimulation[1]
  • to study its effects on lipopolysaccharide-induced anorexia in rats[2]
  • to evaluate the non-specific binding by 5-HT1A receptor binding assays[3]

Biochem./physiol. Wirkung

Metergoline is an ergot alkaloid[4] and a selective serotonin antagonist which blocks the 5-HT2A and 5-HT2C receptors with higher affinity.[5] It possesses antifungal activity against infection caused by Candida krusei.[6] Metergoline exhibits a therapeutic effect against premenstrual dysphoric disorder. It also exhibits antipyretic and analgesic activities.[7]

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

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

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCCL4038
BCCL9897
BCCL0669
BCCH9470
BCCG9869

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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
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
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
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
Catherine A Roca et al.
The American journal of psychiatry, 159(11), 1876-1881 (2002-11-02)
The authors investigated the role of acute serotonergic modulation in the efficacy of selective serotonin reuptake inhibitors (SSRIs) in women with premenstrual dysphoric disorder. Patients with premenstrual dysphoric disorder (whose symptoms had remitted during treatment with fluoxetine) and a group
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