TRIMETHIDINIUM METHOSULFATE

US Previously Marketed

First approved in 1959

Details

Stereochemistry	UNKNOWN
Molecular Formula	C17H36N2.2CH3O4S
Molecular Weight	490.675
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TRIMETHIDINIUM METHOSULFATE

Structure Search

SMILES

COS([O-])(=O)=O.COS([O-])(=O)=O.CC1(C)C2CCC1(C)C[N+](C)(CCC[N+](C)(C)C)C2

InChI

InChIKey=ZOSQTCOGKFRDET-UHFFFAOYSA-L

InChI=1S/C17H36N2.2CH4O4S/c1-16(2)15-9-10-17(16,3)14-19(7,13-15)12-8-11-18(4,5)6;2*1-5-6(2,3)4/h15H,8-14H2,1-7H3;2*1H3,(H,2,3,4)/q+2;;/p-2

HIDE SMILES / InChI

Molecular Formula	CH3O4S
Molecular Weight	111.097
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H36N2
Molecular Weight	268.4811
Charge	2
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13859541 | Elks, J. (2014) The Dictionary of Drugs: Chemical Data, page 1247, retrieved from: https://books.google.ru/books?id=0vXTBwAAQBAJ | Morton, I.K., Hall, J.M. (2012) Concise Dictionary of Pharmacological Agents, page 281, retrieved from: https://books.google.ru/books?id=tsjrCAAAQBAJ

Trimethidinium is a bisquaternary amine ganglion blocking agent with antihypertensive actions. Administration of the drug results in a decrease in blood pressure in the systemic and pulmonary arteries and the right atrium. Associated with these decreased pressures, the stroke volume decreased, but there was sufficient increase in cardiac rate so that cardiac output did not change significantly. Both right and left ventricular work decreased significantly while left ventricular myocardial oxygen consumption was unchanged and calculated cardiac efficiency decreased. Associated side effects on the gastrointestinal tract are reported to be mild and easily controlled when compared with those of pentapyrrolidinium and mecamylamine.

Approval Year

Doses

Dose	Population	Adverse events
300 mg 1 times / day steady, oral Studied dose Dose: 300 mg, 1 times / day Route: oral Route: steady Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14431862	unhealthy, 19-61 years Health Status: unhealthy Age Group: 19-61 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14431862	Other AEs: Paralytic ileus, Constipation... Other AEs: Paralytic ileus (1 patient) Constipation (mild, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/14431862

AEs

AE	Significance	Dose	Population
Paralytic ileus	1 patient	300 mg 1 times / day steady, oral Studied dose Dose: 300 mg, 1 times / day Route: oral Route: steady Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14431862	unhealthy, 19-61 years Health Status: unhealthy Age Group: 19-61 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14431862
Constipation	mild, 1 patient	300 mg 1 times / day steady, oral Studied dose Dose: 300 mg, 1 times / day Route: oral Route: steady Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14431862	unhealthy, 19-61 years Health Status: unhealthy Age Group: 19-61 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14431862

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1B86
Alfa Chemistry	65488
Alfa Chemistry	ACM14149430
Alinda	IBS-E0001927
Asinex	BAS 00347566
Aurora Fine Chemicals LLC	K02.793.510	http://online.aurorafinechemicals.com/info?ID=K02.793.510
ChemDiv	0180-0432
Chemspace	CSSS00160633551	https://chem-space.com/CSSS00160633551
eMolecules	1201272
eMolecules	33575177
IBScreen	STOCK1N-26341
Lab Network	LN00393139
mcule	MCULE-4484204683	https://mcule.com/MCULE-4484204683/
MolPort	MolPort-000-727-648
Pharmeks	PHAR038920
Vitas-M Laboratory	STL552870
ZINC	ZINC000000000810	http://zinc15.docking.org/substances/ZINC000000000810
ZINC	ZINC000004611018	http://zinc15.docking.org/substances/ZINC000004611018
ZINC	ZINC000100375648	http://zinc15.docking.org/substances/ZINC000100375648
ZINC	ZINC000100375651	http://zinc15.docking.org/substances/ZINC000100375651
ZINC	ZINC000239306248	http://zinc15.docking.org/substances/ZINC000239306248

PubMed

Title	Date	PubMed
[Effect of hypotensive agents on return of venous blood to the heart].	1982-03-01	6122601
Vasopressin and beta-endorphin release after osmotic and non-osmotic stimuli: effect of naloxone and dexamethasone.	1982-02-05	6277672
Effect of isoprenaline and trimethidinium on the plasma vasopressin concentration in conscious rats.	1980-06	6996629
[Double controlled regulation of renin release by the sympathetic nervous system. Stimulation via beta receptors and inhibition via alpha receptors].	1977-09-29	199532
alpha-Adrenoceptor-mediated inhibitory effect of the sympathetic nervous system on the isoprenaline-induced increase in plasma renin concentration.	1977-08	198679
Cholinergic agents affect two receptors that modulate transmitter release at a central synapse in Aplsia californica.	1975-05-09	166727
[TREATMENT OF HYPERTENSION WITH CAMPHONIUM].	1963-10	14131716
Acute systemic and coronary hemodynamic effects of trimethidinium methosulfate.	1962-05	13859541
[On the pharmacology of Camphonium].	1962-03-01	14495329
A controlled clinical comparison of guanethidine and trimethidinium methosulfate.	1962-02	14476712

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:22:38 GMT 2025` Edited by `admin` on `Mon Mar 31 19:22:38 GMT 2025`
Record UNII	C1O32IJ4HS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMETHIDINIUM METHOSULFATE

Official Name

English

1,3,8,8-TETRAMETHYL-3-(3-(TRIMETHYLAMMONIO)PROPYL)-3-AZONIABICYCLO(3.2.1)OCTANE BIS(METHYL SULFATE)

Preferred Name

English

TRIMETHIDINIUM METHOSULPHATE

Common Name

English

trimethidinium methosulfate [INN]

Common Name

English

TRIMETHIDINIUM METHOSULFATE [JAN]

Common Name

English

TRIMETHIDINIUM METHOSULFATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C270