MESULERGINE

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 Search

SMILES

CN(C)S(=O)(=O)N[C@H]1C[C@H]2[C@@H](CC3=CN(C)C4=C3C2=CC=C4)N(C)C1

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

Molecular Formula	C18H26N4O2S
Molecular Weight	362.49
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3517235 | https://www.ncbi.nlm.nih.gov/pubmed/6855451

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

Targets

Primary Target	Pharmacology	Potency
Serotonin 2a (5-HT2a) receptor 237 Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7938165	Antagonist 2849	2.0 nM [Ki]
Serotonin 2c (5-HT2c) receptor 131 Target ID: CHEMBL324 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27061981	Antagonist 2849	1.9 nM [Ki]
Dopamine D2 receptor 311 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6230246\|https://www.ncbi.nlm.nih.gov/pubmed/12648304\|https://www.ncbi.nlm.nih.gov/pubmed/6468500\|https://www.ncbi.nlm.nih.gov/pubmed/10650171	Partial Agonist 297	8.0 nM [Ki]

PubMed

Title	Date	PubMed
Reversal of haloperidol-induced motor deficits by mianserin and mesulergine in rats.	2011-01	21190911
Successful drug development despite adverse preclinical findings part 2: examples.	2010-12	22272032
Clozapine and other competitive antagonists reactivate risperidone-inactivated h5-HT7 receptors: radioligand binding and functional evidence for GPCR homodimer protomer interactions.	2010-12	20827463
Electrophysiological effects of SKF83959 on hippocampal CA1 pyramidal neurons: potential mechanisms for the drug's neuroprotective effects.	2010-10-01	20957037
Impact of RNA editing on functions of the serotonin 2C receptor in vivo.	2010	20582266
Upregulation of 5-HT2C receptors in hippocampus of pilocarpine-induced epileptic rats: antagonism by Bacopa monnieri.	2009-10	19700373
Down-regulation of cerebellar 5-HT(2C) receptors in pilocarpine-induced epilepsy in rats: therapeutic role of Bacopa monnieri extract.	2009-09-15	19439326
The sedating antidepressant trazodone impairs sleep-dependent cortical plasticity.	2009-07-01	19568418
Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects.	2009-06-05	19503734
Distribution and neurochemical characterization of neurons within the nucleus of the solitary tract responsive to serotonin agonist-induced hypophagia.	2009-01-03	18762217
Assessing the neuronal serotonergic target-based antidepressant stratagem: impact of in vivo interaction studies and knockout models.	2008-09	19506722
Ligand sensitivity in dimeric associations of the serotonin 5HT2c receptor.	2008-04	18344975
Serotonin activates presynaptic and postsynaptic receptors in rat globus pallidus.	2008-04	18234984
Inverse agonist and neutral antagonist actions of antidepressants at recombinant and native 5-hydroxytryptamine2C receptors: differential modulation of cell surface expression and signal transduction.	2008-03	18083778
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.	2007-11-22	17692935
Diabetes-induced changes in 5-hydroxytryptamine modulation of vagally-induced bradycardia in rat heart.	2007-11	17880377
[The role of serotonergic 2C receptors in neurobiology and treatment of eating disorders].	2007-01	22466431
Reanalysis of constitutively active rat and human 5-HT7(a) receptors in HEK-293F cells demonstrates lack of silent properties for reported neutral antagonists.	2006-10	16967291
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006-03-27	16545797
Heterologous desensitization is evoked by both agonist and antagonist stimulation of the human 5-HT(7) serotonin receptor.	2006-02-17	16487959
Effects of mu-CPP and mesulergine on dietary choices in deprived rats: possible mechanisms of their action.	2006-01	16242827
Decreased agonist, but not antagonist, binding to the naturally occurring Thr92Lys variant of the h5-HT7(a) receptor.	2005-08	15896881
The role of the phosphatidyinositol-linked D1 dopamine receptor in the pharmacology of SKF83959.	2005-04	15820529
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.	2005-03	15499574
Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs.	2005-01	15726452
Involvement of 5-hydroxytryptamine (HT)7 receptors in the 5-HT excitatory effects on the rat urinary bladder.	2004-11	15541139
Serotonin-induced phase advances of SCN neuronal firing in vitro: a possible role for 5-HT5A receptors?	2004-11	15352136
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.	2004-08	15322733
A 5-HT2C agonist elicits hyperactivity and oral dyskinesia with hypophagia in rabbits.	2004-08	15234597
Effects of EGIS-7625, a selective and competitive 5-HT2B receptor antagonist.	2004-04-27	15107597
8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production.	2004-01	14654097
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.	1998-09	9730917
Functional characterisation of the human cloned 5-HT7 receptor (long form); antagonist profile of SB-258719.	1998-07	9720804
[3H]Rauwolscine: an antagonist radioligand for the cloned human 5-hydroxytryptamine2b (5-HT2B) receptor.	1998-01	9459568
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).	1997-09	9298538
Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor.	1997-09	9284367
Activating mutations of the serotonin 5-HT2C receptor.	1997-09	9282936
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.	1997-04-01	9225298
Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities.	1996-01-12	8534270
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.	1996-01	8522988
Species variations in transmembrane region V of the 5-hydroxytryptamine type 2A receptor alter the structure-activity relationship of certain ergolines and tryptamines.	1994-02	8114677
Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.	1993-11-05	8226867
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.	1993-08-25	8394362
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.	1993-08	8394987
Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.	1993-03	8450835
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.	1993-03	7680751
The effect of serotonergic agents on haloperidol-induced catalepsy.	1990	2250574
The binding of serotonergic ligands to the porcine choroid plexus: characterization of a new type of serotonin recognition site.	1984-11-27	6519175
Mechanism of action and tolerance of mesulergine.	1984-11	6488683
Treatment of Parkinson's disease with 8-alpha-amino-ergoline, CU 32-085.	1983-04	6682193

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:19:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:19:54 GMT 2025`
Record UNII	SML95FK06I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Mesulergine [WHO-DD]

Preferred Name

English

MESULERGINE

Official 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