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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H26N4O2S
Molecular Weight 362.49
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MESULERGINE

SMILES

[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@@]1([H])C[C@@H](CN2C)NS(=O)(=O)N(C)C

InChI

InChIKey=JLVHTNZNKOSCNB-YSVLISHTSA-N
InChI=1S/C18H26N4O2S/c1-20(2)25(23,24)19-13-9-15-14-6-5-7-16-18(14)12(10-21(16)3)8-17(15)22(4)11-13/h5-7,10,13,15,17,19H,8-9,11H2,1-4H3/t13-,15+,17+/m0/s1

HIDE SMILES / InChI
Mesulergine, an antagonist of 5-HT2C, and dopamine receptors was studied in clinical trials for the treatment of Parkinson's disease. However, further, development was discontinued due to toxicological observations in animal experiments.

Approval Year

PubMed

PubMed

TitleDatePubMed
Treatment of Parkinson's disease with 8-alpha-amino-ergoline, CU 32-085.
1983 Apr
Mechanism of action and tolerance of mesulergine.
1984 Nov
The binding of serotonergic ligands to the porcine choroid plexus: characterization of a new type of serotonin recognition site.
1984 Nov 27
The effect of serotonergic agents on haloperidol-induced catalepsy.
1990
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.
1993 Aug
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
1993 Aug 25
Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.
1993 Mar
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
Species variations in transmembrane region V of the 5-hydroxytryptamine type 2A receptor alter the structure-activity relationship of certain ergolines and tryptamines.
1994 Feb
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
1996 Jan
Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities.
1996 Jan 12
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.
1997 Apr-May
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).
1997 Sep
Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor.
1997 Sep
Activating mutations of the serotonin 5-HT2C receptor.
1997 Sep
[3H]Rauwolscine: an antagonist radioligand for the cloned human 5-hydroxytryptamine2b (5-HT2B) receptor.
1998 Jan
Functional characterisation of the human cloned 5-HT7 receptor (long form); antagonist profile of SB-258719.
1998 Jul
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.
1998 Sep
Effects of EGIS-7625, a selective and competitive 5-HT2B receptor antagonist.
2003 Sep-Nov
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
2004 Aug
A 5-HT2C agonist elicits hyperactivity and oral dyskinesia with hypophagia in rabbits.
2004 Aug
8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production.
2004 Jan
Involvement of 5-hydroxytryptamine (HT)7 receptors in the 5-HT excitatory effects on the rat urinary bladder.
2004 Nov
Serotonin-induced phase advances of SCN neuronal firing in vitro: a possible role for 5-HT5A receptors?
2004 Nov
The role of the phosphatidyinositol-linked D1 dopamine receptor in the pharmacology of SKF83959.
2005 Apr
Decreased agonist, but not antagonist, binding to the naturally occurring Thr92Lys variant of the h5-HT7(a) receptor.
2005 Aug
Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs.
2005 Jan
A serotonin receptor antagonist induces oocyte maturation in both frogs and mice: evidence that the same G protein-coupled receptor is responsible for maintaining meiosis arrest in both species.
2005 Mar
Heterologous desensitization is evoked by both agonist and antagonist stimulation of the human 5-HT(7) serotonin receptor.
2006 Feb 17
Effects of mu-CPP and mesulergine on dietary choices in deprived rats: possible mechanisms of their action.
2006 Jan
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.
2006 Mar 27
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
[The role of serotonergic 2C receptors in neurobiology and treatment of eating disorders].
2007 Jan
Diabetes-induced changes in 5-hydroxytryptamine modulation of vagally-induced bradycardia in rat heart.
2007 Nov
Stimulation of 5-HT1A, 5-HT1B, 5-HT2A/2C, 5-HT3 and 5-HT4 receptors or 5-HT uptake inhibition: short- and long-term memory.
2007 Nov 22
Ligand sensitivity in dimeric associations of the serotonin 5HT2c receptor.
2008 Apr
Serotonin activates presynaptic and postsynaptic receptors in rat globus pallidus.
2008 Apr
Inverse agonist and neutral antagonist actions of antidepressants at recombinant and native 5-hydroxytryptamine2C receptors: differential modulation of cell surface expression and signal transduction.
2008 Mar
Assessing the neuronal serotonergic target-based antidepressant stratagem: impact of in vivo interaction studies and knockout models.
2008 Sep
Distribution and neurochemical characterization of neurons within the nucleus of the solitary tract responsive to serotonin agonist-induced hypophagia.
2009 Jan 3
The sedating antidepressant trazodone impairs sleep-dependent cortical plasticity.
2009 Jul 1
Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects.
2009 Jun 5
Upregulation of 5-HT2C receptors in hippocampus of pilocarpine-induced epileptic rats: antagonism by Bacopa monnieri.
2009 Oct
Down-regulation of cerebellar 5-HT(2C) receptors in pilocarpine-induced epilepsy in rats: therapeutic role of Bacopa monnieri extract.
2009 Sep 15
Impact of RNA editing on functions of the serotonin 2C receptor in vivo.
2010
Successful drug development despite adverse preclinical findings part 2: examples.
2010 Dec
Clozapine and other competitive antagonists reactivate risperidone-inactivated h5-HT7 receptors: radioligand binding and functional evidence for GPCR homodimer protomer interactions.
2010 Dec
Electrophysiological effects of SKF83959 on hippocampal CA1 pyramidal neurons: potential mechanisms for the drug's neuroprotective effects.
2010 Oct 1
Reversal of haloperidol-induced motor deficits by mianserin and mesulergine in rats.
2011 Jan

Sample Use Guides

Initial dose were 0-5 mg mesulergine once a day. Doses were increased every 3-4 days by increments of 0-5 mg. Mesulergine the daily dose being distributed over 2-4 intakes. After the 20th day of treatment the daily dose was increased every 3-4 days by increments of 1- 0 mg, until a satisfactory therapeutic response was obtained or until significant side-effects appeared. Maximum daily doses of mesulergine was 30 mg.
Route of Administration: Oral
Name Type Language
MESULERGINE
INN   WHO-DD  
INN  
Official Name English
Mesulergine [WHO-DD]
Common Name English
N'-(1,6-DIMETHYLERGOLIN-8.ALPHA.-YL)-N,N-DIMETHYLSULFAMIDE
Systematic Name English
mesulergine [INN]
Common Name English
{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0{2,7}.0{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]sulfamoyl}dimethylamine
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL12314
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
PRIMARY
EVMPD
SUB08793MIG
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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NCI_THESAURUS
C83940
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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MESH
C031649
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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CHEBI
73378
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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INN
5161
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EPA CompTox
DTXSID3046324
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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SMS_ID
100000081169
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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WIKIPEDIA
MESULERGINE
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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PUBCHEM
68848
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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CAS
64795-35-3
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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FDA UNII
SML95FK06I
Created by admin on Fri Dec 15 16:07:53 GMT 2023 , Edited by admin on Fri Dec 15 16:07:53 GMT 2023
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