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
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
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.
1992 Jun 15
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
Effects of serotoninergic drugs on tremor induced by physostigmine in rats.
2000 May
Discriminative stimulus properties of indorenate, a 5-HT1A, 5-HT1B and 5-HT2C agonist: a study in rats.
2001 Mar
Pregnancy termination in the bitch and queen.
2002 Aug
Pharmacological activity of hyperforin acetate in rats.
2002 Dec
Calcium-antagonistic activity of sumatriptan in the rat anococcygeus muscle.
2002 Jan
Serotonin sets the day state in the neurons that control coupling between the optic lobe circadian pacemakers in the cricket Gryllus bimaculatus.
2002 May
Effects of metergoline on symptoms in women with premenstrual dysphoric disorder.
2002 Nov
Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors.
2003 Jan
Effect of fenfluramine on caloric intake and macronutrient selection in Lou/c rats during aging.
2003 Jan-Feb
Serotonin regulates rhythmic whisking.
2003 Jul 17
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
2004 Aug
Involvement of mast cells in basal and neurotensin-induced intestinal absorption of taurocholate in rats.
2004 Aug
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
2004 Jan 26
Serotonin reuptake inhibitors do not prevent 5,7-dihydroxytryptamine-induced depletion of serotonin in rat brain.
2004 May 8
Serotonin-induced enhancement of vasopressin and oxytocin secretion in rat neurohypophyseal tissue culture.
2005 Apr 15
Anoestrus in the dog: a fascinating story.
2006 Aug
Possible involvement of endogenous 5-HT in aggravation of cerulein-induced acute pancreatitis in mice.
2007 Nov
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
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
On the intrinsic regulation of neuropeptide Y release in the mammalian suprachiasmatic nucleus circadian clock.
2010 Mar
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 UTC 2023 , Edited by admin on Fri Dec 15 14:58:03 UTC 2023
WHO-ATC G02CB05
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WHO-VATC QG02CB05
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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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PRIMARY
RXCUI
6834
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PRIMARY RxNorm
DRUG CENTRAL
1723
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PRIMARY
NSC
755878
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PRIMARY
NCI_THESAURUS
C91039
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ECHA (EC/EINECS)
241-686-3
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CAS
17692-51-2
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FDA UNII
1501393LY5
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PRIMARY