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

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 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
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.	1992 Jun 15	1608964
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.	1993 Aug 25	8394362
Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization.	1993 Mar	8450829
Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.	1993 Nov 5	8226867
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
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.	1996 Jan	8522988
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 Nov	8863519
GR127935 acts as a partial agonist at recombinant human 5-HT1D alpha and 5-HT1D beta receptors.	1996 Oct 31	8957260
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
Functional characterisation of the human cloned 5-HT7 receptor (long form); antagonist profile of SB-258719.	1998 Jul	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 Mar	9550290
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.	1998 Nov	9798944
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.	1998 Sep	9730917
Inverse agonism and constitutive activity as functional correlates of serotonin h5-HT(1B) receptor/G-protein stoichiometry.	2000 Nov	11040052
Specific labelling of serotonin 5-HT(1B) receptors in rat frontal cortex with the novel, phenylpiperazine derivative, [3H]GR125,743. A pharmacological characterization.	2002 Apr	11888550
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.	2004 Jan 26	14744596
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.	2004 Oct	15482641
Serotonin (5HT), fluoxetine, imipramine and dopamine target distinct 5HT receptor signaling to modulate Caenorhabditis elegans egg-laying behavior.	2005 Mar	15654117
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006 Mar 27	16545797
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 Feb	18996971
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 Feb	23243064

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:31:38 UTC 2023` Edited by `admin` on `Sat Dec 16 17:31:38 UTC 2023`
Record UNII	55D94103HL
Record Status	`Validated (UNII)`
Record Version

Download

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