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
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
A 5-HT(7) receptor-mediated depolarization in the anterodorsal thalamus. I. Pharmacological characterization.	2001 Apr	11259568
Pharmacological characterisation of human 5-HT2 receptor subtypes.	2001 Feb 23	11230991
[(3)H]-serotonin release from bovine iris-ciliary body: pharmacology of prejunctional serotonin (5-HT(7)) autoreceptors.	2001 Jul	11428863
Calcium-antagonistic activity of sumatriptan in the rat anococcygeus muscle.	2002 Jan	11731721
The human 5-HT7 serotonin receptor splice variants: constitutive activity and inverse agonist effects.	2002 Mar	11906971
5-HT(2) receptor-mediated phosphoinositide hydrolysis in bovine ciliary epithelium.	2003 Feb	12648304
5-HT7 receptor-mediated relaxation of the oviduct in nonpregnant proestrus pigs.	2003 Feb 14	12586216
Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors.	2003 Jan	12479957
Insulin signaling inhibits the 5-HT2C receptor in choroid plexus via MAP kinase.	2003 Jun 9	12795815
Effects of EGIS-7625, a selective and competitive 5-HT2B receptor antagonist.	2003 Sep-Nov	15107597
8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production.	2004 Jan	14654097
Involvement of 5-hydroxytryptamine (HT)7 receptors in the 5-HT excitatory effects on the rat urinary bladder.	2004 Nov	15541139
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	15499574
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
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	18083778
The sedating antidepressant trazodone impairs sleep-dependent cortical plasticity.	2009 Jul 1	19568418
Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects.	2009 Jun 5	19503734
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 GMT 2023` Edited by `admin` on `Fri Dec 15 16:07:53 GMT 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