U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H29N3O2
Molecular Weight 403.5167
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METERGOLINE

SMILES

[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@@]1([H])C[C@@H](CNC(=O)OCC5=CC=CC=C5)CN2C

InChI

InChIKey=WZHJKEUHNJHDLS-QTGUNEKASA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11910270 | https://www.ncbi.nlm.nih.gov/pubmed/12411222 | https://www.ncbi.nlm.nih.gov/pubmed/27251511 | https://www.ncbi.nlm.nih.gov/pubmed/8650684 |

Metergoline is a psychoactive drug of the ergoline chemical class which acts as a ligand for various serotonin and dopamine receptors. Metergoline is an antagonist at various 5-HT receptor subtypes at a relatively low concentration and an agonist at dopamine receptors. Its use has been studied in various clinical settings such as a treatment for seasonal affective disorder, prolactin hormone regulation due to its inhibitory effect on prolactin release premenstrual dysphoric disorder in women and antianxiety treatment

Originator

Sources: Gazzetta Chimica Italiana (1964), 94, (8-9), 936-46.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Determination of the role of serotonergic and cholinergic systems in apomorphine--induced aggressiveness in rats.
1979 Mar-Apr
The influence of 5-HT receptor blocking agents on the behavioral effects of analgesics in rats.
1980
Pharmacology in vivo of the phenylindan derivative, Lu 19-005, a new potent inhibitor of dopamine, noradrenaline and 5-hydroxytryptamine uptake in rat brain.
1985 Apr
Central antiserotonergic and antidopaminergic action of pirenperone, a putative 5-HT2 receptor antagonist.
1985 Mar-Apr
Antagonism of drug-induced yawning and penile erections in rats.
1986 Mar 18
Effect of metergoline, fenfluramine, and 8-OHDPAT on catalepsy induced by haloperidol or morphine.
1988 Aug
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.
1991 Aug
Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.
1993 Jan 15
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.
1993 Mar
Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.
1993 Nov 5
Cloning and characterisation of the human 5-HT5A serotonin receptor.
1994 Dec 5
Gonadal steroids, brain, and behavior: role of context.
2002 Jun
Reproductive hormonal treatments for mood disorders in women.
2002 Jun
Midbrain raphe modulation of nonphotic circadian clock resetting and 5-HT release in the mammalian suprachiasmatic nucleus.
2003 Aug 20
Treatment of seasonal affective disorders.
2003 Dec
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells.
2003 Nov
Study of the behavioural responses related to the potential addictive properties of MDMA in mice.
2004 Mar
Updated overview of the putative role of the serotoninergic system in obsessive-compulsive disorder.
2005 Sep
Anoestrus in the dog: a fascinating story.
2006 Aug
Serotonergic mediation of constant light-potentiated nonphotic phase shifting of the circadian locomotor activity rhythm in Syrian hamsters.
2006 Jul
Effects of dopamine D1-like receptor agonists on food-maintained operant behavior in rats.
2006 Jun
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.
2006 Mar 27
Clozapine modulates aromatic L-amino acid decarboxylase activity in mouse striatum.
2006 May
Systemic morphine produce antinociception mediated by spinal 5-HT7, but not 5-HT1A and 5-HT2 receptors in the spinal cord.
2006 Nov
Reanalysis of constitutively active rat and human 5-HT7(a) receptors in HEK-293F cells demonstrates lack of silent properties for reported neutral antagonists.
2006 Oct
Dopamine agonists, anti-progestins, anti-androgens, long-term-release GnRH agonists and anti-estrogens in canine reproduction: a review.
2006 Oct
Serotonin increases the phase shift of the circadian locomotor activity rhythm in mice after dark pulses in constant light conditions.
2007
In vivo Schild regression analyses using nonselective 5-HT2C receptor antagonists in a rat operant behavioral assay.
2007 Aug
Anxiolytic-like effect of group III mGlu receptor antagonist is serotonin-dependent.
2007 Feb
Feeding behavior after metergoline or GR-46611 injections into the paraventricular nucleus of the hypothalamus in the pigeon.
2007 May 16
Possible involvement of endogenous 5-HT in aggravation of cerulein-induced acute pancreatitis in mice.
2007 Nov
Anxiolytic-like action of MTEP expressed in the conflict drinking Vogel test in rats is serotonin dependent.
2007 Nov
The structure of human serotonin 2c G-protein-coupled receptor bound to agonists and antagonists.
2008 Aug
Selective serotonin reuptake inhibitors: a review of its effects on intraocular pressure.
2008 Dec
Physiology of the canine anoestrus and methods for manipulation of its length.
2008 Jul
The effects of metergoline and 8-OH-DPAT injections into arcuate nucleus and lateral hypothalamic area on feeding in female rats during the estrous cycle.
2008 Oct 20
Panic disorder: is the PAG involved?
2009
Antidepressant-like effects of glucagon-like peptide-2 in mice occur via monoamine pathways.
2009 Dec 1
Tonic serotonergic control of ingestive behaviours in the pigeon (Columba livia): the role of the arcopallium.
2009 Dec 28
Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists.
2009 Feb
cis-Urocanic acid stimulates primary human keratinocytes independently of serotonin or platelet-activating factor receptors.
2009 Nov
The bovine mammary gland expresses multiple functional isoforms of serotonin receptors.
2009 Oct
Human 5-HT7 receptor-induced inactivation of forskolin-stimulated adenylate cyclase by risperidone, 9-OH-risperidone and other "inactivating antagonists".
2009 Sep
Serotonergic-postsynaptic receptors modulate gripping-induced immobility episodes in male taiep rats.
2009 Sep
5-hydroxy-L-tryptophan Suppressed Food Intake in Rats Despite an Increase in the Arcuate NPY Expression.
2010 Dec
On the mechanism of the antidepressant-like action of group II mGlu receptor antagonist, MGS0039.
2010 Dec
A role for serotonin in the antidepressant activity of NG-Nitro-L-arginine, in the rat forced swimming test.
2010 Feb
On the intrinsic regulation of neuropeptide Y release in the mammalian suprachiasmatic nucleus circadian clock.
2010 Mar
In vitro synergistic effects of metergoline and antifungal agents against Candida krusei.
2010 Nov
Evaluation of [(11)C]metergoline as a PET radiotracer for 5HTR in nonhuman primates.
2010 Nov 15
Patents

Patents

Sample Use Guides

from 7.5 mg/day to 40 mg/day
Route of Administration: Oral
Oocytes were injected with human Kv1.4 channel cRNAs and maintained for 2 to 4 d before Kv1.4 channel currents were recorded in ND96 using a two-electrode voltage clamp technique. Original K+ current traces are shown under control conditions, after bath superfusion of metergoline and washout. Voltage pulses of 500-ms duration were applied in 10-mV increments and at 10-s intervals from a holding potential of –80 mV. I–V relationships of human Kv1.4 channels were recorded in the absence or presence of 10 μM metergoline (MG). The current-voltage relationships of Kv1.4 channels were obtained using voltage steps between –80 and +60 mV taken in 10 mV increments.
Name Type Language
METERGOLINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
FI 6337
Code English
NSC-755878
Code English
FI-6337
Code English
(+)-N-(CARBOXY)-1-METHYL-9,10-DIHYDROLYSERGAMINE BENZYL ESTER
Common Name English
METERGOLINE [MI]
Common Name English
metergoline [INN]
Common Name English
METERGOLINE [MART.]
Common Name English
MCE
Code English
Metergoline [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 14:58:03 GMT 2023 , Edited by admin on Fri Dec 15 14:58:03 GMT 2023
WHO-ATC G02CB05
Created by admin on Fri Dec 15 14:58:03 GMT 2023 , Edited by admin on Fri Dec 15 14:58:03 GMT 2023
WHO-VATC QG02CB05
Created by admin on Fri Dec 15 14:58:03 GMT 2023 , Edited by admin on Fri Dec 15 14:58:03 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID5042584
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PRIMARY
PUBCHEM
28693
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ChEMBL
CHEMBL19215
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MESH
D008711
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MERCK INDEX
m7279
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PRIMARY Merck Index
SMS_ID
100000081202
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INN
2378
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WIKIPEDIA
METERGOLINE
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EVMPD
SUB08824MIG
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DRUG BANK
DB13520
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CHEBI
64216
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RXCUI
6834
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PRIMARY RxNorm
DRUG CENTRAL
1723
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NSC
755878
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NCI_THESAURUS
C91039
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ECHA (EC/EINECS)
241-686-3
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CAS
17692-51-2
Created by admin on Fri Dec 15 14:58:03 GMT 2023 , Edited by admin on Fri Dec 15 14:58:03 GMT 2023
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FDA UNII
1501393LY5
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