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=CC2=C(SC3=C(CC2N4CCN(C)CC4)C=CC=C3)C=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

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 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27487565 \| https://www.ncbi.nlm.nih.gov/pubmed/15322733	Antagonist 2778	56.0 nM [IC50]
Serotonin 2b (5-HT2b) receptor 60 Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15322733	Antagonist 2778	8.68 null [pKi]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15322733	Antagonist 2778	8.35 null [pKi]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27487565	Antagonist 2778	71.0 nM [IC50]
Serotonin 6 (5-HT6) receptor 45 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25557493	Antagonist 2778	4.7 nM [IC50]
Serotonin 7 (5-HT7) receptor 31 Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805037	Antagonist 2778	1.5 nM [IC50]
Dopamine D1 receptor 101 Target ID: CHEMBL265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11784139	Antagonist 2778	2.0 nM [Ki]
Dopamine D2 receptor 297 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11784139	Antagonist 2778	0.4 nM [Ki]

PubMed

Title	Date	PubMed
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.	1991 Aug	1652050
Two members of a distinct subfamily of 5-hydroxytryptamine receptors differentially expressed in rat brain.	1993 Apr 15	7682702
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.	1993 Aug	8394987
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.	1993 Aug 25	8394362
Involvement of brain serotonergic function in lidocaine-induced convulsions in mice.	1993 Jul	8411779
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.	1993 Mar	7680751
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 Dec	8967979
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.	1997 Apr-May	9225298
Cloning and characterization of the guinea pig 5-HT1F receptor subtype: a comparison of the pharmacological profile to the human species homolog.	1997 Apr-May	9225282
Characterization of human serotonin 1D and 1B receptors using [3H]-GR-125743, a novel radiolabelled serotonin 5HT1D/1B receptor antagonist.	1997 Sep	9303569
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
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998 Aug 21	9760039
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 Mar	9550290
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.	1998 Sep	9730917
Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor.	1999 Sep 10	10513577
The role of serotonin(2) receptors in mediating cocaine-induced convulsions.	2000 Apr	10764922
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells.	2003 Nov	14578406
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.	2004 Aug	15322733
Involvement of some 5-HT receptors in methamphetamine-induced locomotor activity in mice.	2004 Jun	15213358
Serotonin (5HT), fluoxetine, imipramine and dopamine target distinct 5HT receptor signaling to modulate Caenorhabditis elegans egg-laying behavior.	2005 Mar	15654117

Name

Type

Language

METITEPINE

Official 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

metitepine [INN]

Common Name

English

Code System Code Type Description

CAS

20229-30-5