TROPANSERIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H23NO2
Molecular Weight	273.37
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C3=CC(C)=CC(C)=C3

InChI

InChIKey=HDDNYFLPWFSBLN-ZSHCYNCHSA-N

InChI=1S/C17H23NO2/c1-11-6-12(2)8-13(7-11)17(19)20-16-9-14-4-5-15(10-16)18(14)3/h6-8,14-16H,4-5,9-10H2,1-3H3/t14-,15+,16+

HIDE SMILES / InChI

Molecular Formula	C17H23NO2
Molecular Weight	273.37
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/6472484 | https://www.ncbi.nlm.nih.gov/pubmed/28025094 | https://www.karger.com/Article/Abstract/411517

Tropanserin (MDL 72422) is a potent and selective 5-HT3 receptor antagonist. It was investigated as a drug for the treatment of migraine. MDL 72222 was shown to be an effective antimigraine agent in a double-blind placebo-controlled study.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2111332 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D06253 \| https://www.ncbi.nlm.nih.gov/pubmed/1338307 \| https://www.ncbi.nlm.nih.gov/pubmed/2141798 \| https://www.ncbi.nlm.nih.gov/pubmed/6472484 \| https://www.ncbi.nlm.nih.gov/pubmed/2562495	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 107 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3893732 https://www.ncbi.nlm.nih.gov/pubmed/3709648 https://www.ncbi.nlm.nih.gov/pubmed/28025094	Primary		Phase II 1147	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ChemBridge	5254007	http://www.hit2lead.com/screening-compounds/5254007
ChemDiv	4480-0919	http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=4480-0919
eMolecules	1304629	https://orderbb.emolecules.com/search/#?query=1304629
eMolecules	33422852	https://orderbb.emolecules.com/search/#?query=33422852
Lab Network	LN01043686	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01043686
Lab Network	LN03031447	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN03031447
mcule	HDDNYFLPWFSBLN-UHFFFAOYSA-N	https://mcule.com/HDDNYFLPWFSBLN-UHFFFAOYSA-N/
mcule	MCULE-1343403053	https://mcule.com/MCULE-1343403053/
mcule	MCULE-5176283853	https://mcule.com/MCULE-5176283853/
MolPort	MolPort-001-903-626	https://www.molport.com/shop/molecule-link/MolPort-001-903-626
MolPort	MolPort-002-140-070	https://www.molport.com/shop/molecule-link/MolPort-002-140-070
MuseChem	I010258	https://www.musechem.com/product/I010258.html
Princeton BioMolecular Research	OSSL_457967	http://www.princetonbio.com/order_online?common_id=OSSL_457967
TimTec	ST50975614	http://www.echemstore.com/catalogsearch/result/?q=ST50975614
TimTec	ST51171915	http://www.echemstore.com/catalogsearch/result/?q=ST51171915
Tocris	641	https://www.tocris.com/search.php?Type=QuickSearch&Value=0641

PubMed

Title	Date	PubMed
Analgesia induced by 2- or 100-Hz electroacupuncture in the rat tail-flick test depends on the anterior pretectal nucleus.	2013-11-06	24063986
5-HT3 receptor-dependent modulation of respiratory burst frequency, regularity, and episodicity in isolated adult turtle brainstems.	2010-06-30	20399913
GABA(A) receptors mediate the attenuating effects of a 5-HT(3) receptor antagonist on methamphetamine-induced behavioral sensitization in mice.	2010-04	19953653
5HT2 and 5HT3 receptors' contribution to modeling of post-serotonin respiratory pattern in cats.	2004-09-24	15350826

Patents

Sample Use Guides

In Vivo Use Guide

Forty-seven patients with common (n = 29) or classical (n = 8) migraine or mixed type with or without a psychogenic component (n = 10) received 20-40 mg Tropanserin (MDL-72,422) (n = 24) or placebo (n = 23) intravenously during the headache phase of a migraine attack.

Route of Administration: Intravenous

In Vitro Use Guide

Treatment of rat ganglia with the 5-HT(3) receptor antagonist Tropanserin (MDL 72222) (0.5 uM) during the maintenance phase of established gLTD (1 h after LFS) antagonized the LFS-induced depression.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:13:59 GMT 2025` Edited by `admin` on `Mon Mar 31 19:13:59 GMT 2025`
Record UNII	04B48I6VHR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZOIC ACID, 3,5-DIMETHYL-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER

Preferred Name

English

TROPANSERIN

Official Name

English

tropanserin [INN]

Common Name

English

BENZOIC ACID, 3,5-DIMETHYL-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, ENDO-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885