METITEPINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H24N2S2
Molecular Weight	356.548
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CSC1=CC=C2SC3=CC=CC=C3CC(N4CCN(C)CC4)C2=C1

InChI

InChIKey=RLJFTICUTYVZDG-UHFFFAOYSA-N

InChI=1S/C20H24N2S2/c1-21-9-11-22(12-10-21)18-13-15-5-3-4-6-19(15)24-20-8-7-16(23-2)14-17(18)20/h3-8,14,18H,9-13H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C20H24N2S2
Molecular Weight	356.548
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4340797 | Elks J., The Dictionary of Drugs: Chemical Data: Chemical Data, Structures, retrieved from: https://books.google.ru/books?id=0vXTBwAAQBAJ&pg=PA815&redir_esc=y#v=onepage&q&f=false

Metitepine, a psychotropic agent was developed as a non-selective antagonist of serotonin, dopamine, and adrenergic receptors. Metitepine has never been marketed.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 2a (5-HT2a) receptor 237 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27487565 \| https://www.ncbi.nlm.nih.gov/pubmed/15322733	Antagonist 2849	56.0 nM [IC50]
Serotonin 2b (5-HT2b) receptor 60 Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15322733	Antagonist 2849	8.68 null [pKi]
Serotonin 2c (5-HT2c) receptor 131 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15322733	Antagonist 2849	8.35 null [pKi]
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27487565	Antagonist 2849	71.0 nM [IC50]
Serotonin 6 (5-HT6) receptor 44 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25557493	Antagonist 2849	4.7 nM [IC50]
Serotonin 7 (5-HT7) receptor 30 Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805037	Antagonist 2849	1.5 nM [IC50]
Dopamine D1 receptor 106 Target ID: CHEMBL265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11784139	Antagonist 2849	2.0 nM [Ki]
Dopamine D2 receptor 311 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11784139	Antagonist 2849	0.4 nM [Ki]

PubMed

Title	Date	PubMed
A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis.	2013-02	23243064
Human 5-HT7 receptor-induced inactivation of forskolin-stimulated adenylate cyclase by risperidone, 9-OH-risperidone and other "inactivating antagonists".	2009-09	19509219
Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists.	2009-02	18996971
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006-03-27	16545797
Serotonin (5HT), fluoxetine, imipramine and dopamine target distinct 5HT receptor signaling to modulate Caenorhabditis elegans egg-laying behavior.	2005-03	15654117
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.	2004-10	15482641
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.	2004-08	15322733
Involvement of some 5-HT receptors in methamphetamine-induced locomotor activity in mice.	2004-06	15213358
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.	2004-01-26	14744596
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells.	2003-11	14578406
Specific labelling of serotonin 5-HT(1B) receptors in rat frontal cortex with the novel, phenylpiperazine derivative, [3H]GR125,743. A pharmacological characterization.	2002-04	11888550
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.	2001-06	11414657
Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution.	2001-04-27	11343685
Inverse agonism and constitutive activity as functional correlates of serotonin h5-HT(1B) receptor/G-protein stoichiometry.	2000-11	11040052
The role of serotonin(2) receptors in mediating cocaine-induced convulsions.	2000-04	10764922
Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor.	1999-09-10	10513577
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.	1998-11	9798944
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.	1998-09	9730917
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998-08-21	9760039
Functional characterisation of the human cloned 5-HT7 receptor (long form); antagonist profile of SB-258719.	1998-07	9720804
Labelling of recombinant human and native rat serotonin 5-HT1A receptors by a novel, selective radioligand, [3H]-S 15535: definition of its binding profile using agonists, antagonists and inverse agonists.	1998-03	9550290
[3H]Rauwolscine: an antagonist radioligand for the cloned human 5-hydroxytryptamine2b (5-HT2B) receptor.	1998-01	9459568
Characterization of human serotonin 1D and 1B receptors using [3H]-GR-125743, a novel radiolabelled serotonin 5HT1D/1B receptor antagonist.	1997-09	9303569
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
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.	1997-04-01	9225298
Cloning and characterization of the guinea pig 5-HT1F receptor subtype: a comparison of the pharmacological profile to the human species homolog.	1997-04-01	9225282
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.	1996-12	8967979
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.	1996-11	8863519
GR127935 acts as a partial agonist at recombinant human 5-HT1D alpha and 5-HT1D beta receptors.	1996-10-31	8957260
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.	1996-01	8522988
Cloning and characterisation of the human 5-HT5A serotonin receptor.	1994-12-05	7988681
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
Involvement of brain serotonergic function in lidocaine-induced convulsions in mice.	1993-07	8411779
Two members of a distinct subfamily of 5-hydroxytryptamine receptors differentially expressed in rat brain.	1993-04-15	7682702
Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization.	1993-03	8450829
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.	1993-03	7680751
Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.	1993-01-15	8380639
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.	1992-06-15	1608964
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.	1991-08	1652050
Evidence that central 5-HT1A-receptors play a role in the von Bezold-Jarisch reflex in the rat.	1990-08	2207497
Skeletal muscle necrosis following membrane-active drugs plus serotonin.	1976-05	6632

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:16:22 GMT 2025` Edited by `admin` on `Wed Apr 02 09:16:22 GMT 2025`
Record UNII	55D94103HL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METITEPINE

Official Name

English

metitepine [INN]

Preferred Name

English

RO-8-6837

Code

English

METHIOTHEPIN

Common Name

English

RO 8-6837

Code

English

METHIOTEPIN

Common Name

English

METHIOTHEPINE

Common Name

English

METITEPINE [MI]

Common Name

English

NSC-759875

Code

English

PIPERAZINE, 1-(10,11-DIHYDRO-8-(METHYLTHIO)DIBENZO(B,F)THIEPIN-10-YL)-4-METHYL-

Systematic Name

English

Code System Code Type Description

CAS

20229-30-5