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

[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

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 231 Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7938165	Antagonist 2778	2.0 nM [Ki]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL324 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27061981	Antagonist 2778	1.9 nM [Ki]
Dopamine D2 receptor 297 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 290	8.0 nM [Ki]

PubMed

Title	Date	PubMed
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.	1993 Aug	8394987
Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.	1993 Mar	8450835
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.	1993 Mar	7680751
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.	1997 Apr-May	9225298
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).	1997 Sep	9298538
Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor.	1997 Sep	9284367
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.	1998 Sep	9730917
[(3)H]-serotonin release from bovine iris-ciliary body: pharmacology of prejunctional serotonin (5-HT(7)) autoreceptors.	2001 Jul	11428863
The GR127935-sensitive 5-HT(1) receptors mediating canine internal carotid vasoconstriction: resemblance to the 5-HT(1B), but not to the 5-HT(1D) or 5-ht(1F), receptor subtype.	2001 Mar	11226129
No involvement of 5-HT(7) or 5-HT(1D) receptors in the (R)-8-OH-DPAT-induced depression of the monosynaptic reflex in spinalized rats.	2001 Sep 14	11557264
Neuropharmacological profile of a novel potential atypical antipsychotic drug Y-931 (8-fluoro-12-(4-methylpiperazin-1-yl)- 6H-[1]benzothieno[2,3-b][1,5] benzodiazepine maleate).	2002 Apr	11927170
Up-regulation of 5-HT2B receptor density and receptor-mediated glycogenolysis in mouse astrocytes by long-term fluoxetine administration.	2002 Feb	11930908
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells.	2003 Nov	14578406
8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production.	2004 Jan	14654097
Heterologous desensitization is evoked by both agonist and antagonist stimulation of the human 5-HT(7) serotonin receptor.	2006 Feb 17	16487959
Effects of mu-CPP and mesulergine on dietary choices in deprived rats: possible mechanisms of their action.	2006 Jan	16242827
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006 Mar 27	16545797
[The role of serotonergic 2C receptors in neurobiology and treatment of eating disorders].	2007 Jan	22466431
Diabetes-induced changes in 5-hydroxytryptamine modulation of vagally-induced bradycardia in rat heart.	2007 Nov	17880377
Ligand sensitivity in dimeric associations of the serotonin 5HT2c receptor.	2008 Apr	18344975
Assessing the neuronal serotonergic target-based antidepressant stratagem: impact of in vivo interaction studies and knockout models.	2008 Sep	19506722
Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects.	2009 Jun 5	19503734
Upregulation of 5-HT2C receptors in hippocampus of pilocarpine-induced epileptic rats: antagonism by Bacopa monnieri.	2009 Oct	19700373
Impact of RNA editing on functions of the serotonin 2C receptor in vivo.	2010	20582266
Clozapine and other competitive antagonists reactivate risperidone-inactivated h5-HT7 receptors: radioligand binding and functional evidence for GPCR homodimer protomer interactions.	2010 Dec	20827463
Electrophysiological effects of SKF83959 on hippocampal CA1 pyramidal neurons: potential mechanisms for the drug's neuroprotective effects.	2010 Oct 1	20957037
Reversal of haloperidol-induced motor deficits by mianserin and mesulergine in rats.	2011 Jan	21190911

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 `Fri Dec 15 16:07:53 UTC 2023` Edited by `admin` on `Fri Dec 15 16:07:53 UTC 2023`
Record UNII	SML95FK06I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MESULERGINE

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