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M3668

Sigma-Aldrich

Metergoline

Synonym(s):

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
$147.60
5 G
$1,530.00

About This Item

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

$147.60

List price$164.00Save 10%
Web-Only Promotion

Available to ship onApril 08, 2025Details

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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[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 Actions

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]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCL4038
BCCL9897
BCCL0669
BCCH9470
BCCG9869

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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
K J Miller et al.
European journal of pharmacology, 227(1), 99-102 (1992-09-01)
We have recently cloned a novel human 5-HT1D receptor subtype termed 5-HT1D beta. CHO K1 cells expressing the human serotonin 5-HT1D beta receptor were assayed to determine the second messenger system of this receptor. Cyclic AMP radioimmunoassays revealed that the
Elsa Rouah-Martin et al.
International journal of molecular sciences, 13(12), 17138-17159 (2012-12-18)
Ergot alkaloids are mycotoxins produced by fungi of the genus Claviceps, which infect cereal crops and grasses. The uptake of ergot alkaloid contaminated cereal products can be lethal to humans and animals. For food safety assessment, analytical techniques are currently
Sanna K Janhunen et al.
Obesity (Silver Spring, Md.), 19(10), 1979-1986 (2011-04-09)
Because the use of monoamine reuptake inhibitors as weight-reducing agents is limited by adverse effects, novel antiobesity drugs are needed. We studied acute effects of the noradrenaline (NA) and serotonin (5-HT) reuptake inhibitor sibutramine (SIB), alone and after pretreatment with
A Dogrul et al.
British journal of pharmacology, 149(5), 498-505 (2006-08-22)
The serotonergic system within the spinal cord have been proposed to play an important role in the analgesic effects of systemic morphine. Currently, seven groups of 5-HT receptors (5-HT1-7) have been characterized. One of the most recently identified subtypes of
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