TRAPENCAINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H34N2O3
Molecular Weight	374.517
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCOC1=CC(NC(=O)O[C@@H]2CCCC[C@H]2N3CCCC3)=CC=C1

InChI

InChIKey=HVYGHQWGUABUST-NHCUHLMSSA-N

InChI=1S/C22H34N2O3/c1-2-3-8-16-26-19-11-9-10-18(17-19)23-22(25)27-21-13-5-4-12-20(21)24-14-6-7-15-24/h9-11,17,20-21H,2-8,12-16H2,1H3,(H,23,25)/t20-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H34N2O3
Molecular Weight	374.517
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7993886 | https://www.ncbi.nlm.nih.gov/pubmed/1897435 | https://www.ncbi.nlm.nih.gov/pubmed/3394577

Trapencaine (pentacaine) is a local anesthetic, used as an antiulcerogenic agent. A proportional involvement of local and systemic effects of pentacaine was found in phenylbutazone-induced and cold-resistant stress-induced lesions, whereas in ethanol-induced lesions oral administration was the only effective way. On the other hand, duodenal lesions and gastric acid secretion were substantially affected by parenteral administration. Pentacaine prevented the depletion of mucus after stress in rats. Intraduodenal administration of pentacaine significantly suppressed both the basal and stimulated gastric secretion.

Approval Year

PubMed

Title	Date	PubMed
Study of local anaesthetics: part 201. Determination of the critical micellar concentration of pentacaine hydrochloride from the measurements of UV absorption of pyrene in methanol solutions.	2013-06	23961815
[Study of local anesthetics--part 195. Study of micellization of pentacainium chloride in methanol and ethanol solutions].	2011-12	22312852
Is there a place for local anesthetics structurally different from classical amid or ester local anesthetics?	2006-10	16960483
Differences between gastric antiulcer effects of trapencaine enantiomers.	2003-09	14531465
[Study of local anesthetics. CLVII. Chromatographic properties of pentacaine, carbisocaine, heptacaine and its 3-, and 4-positional isomers in the RP HPLC system].	2001-09	11579689
[Anti-radical activity of certain anti-ulcer agents and local anesthetics].	2001-07	11475894
Gastric transmucosal potential difference: effect of antisecretory and gastroprotective drugs.	1998-03	9510081
Effective one/two step purification of various materials by solid-phase extraction.	1997-12-31	9413613
Gastroprotective effect of stereoisomeric cis- and trans-2-(1-pyrrolidinyl) and 2-(1-pyrrolidinylmethyl)cyclohexyl alkoxycarbanilates in rats.	1997-12	9442559
Effect of pentacaine and its derivatives on the contractile responses of smooth muscle in the guinea-pig stomach.	1996-11-21	8982669
Effect of trapencaine and some of its derivatives on gastric wall mucus in stressed rats.	1995-06	7651982
Comparison of local anesthetic activity of pentacaine (trapencaine) and some of its derivatives by three different techniques.	1993-03	8493287
Determination of pentacaine, trans-2-(1-pyrrolidinyl)cyclohexyl-3-pentyloxycarbanilate hydrochloride, in biological samples by gas chromatography/mass spectrometry.	1985-08	2931128

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:16:45 GMT 2025` Edited by `admin` on `Mon Mar 31 19:16:45 GMT 2025`
Record UNII	6H10WF5D0H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

trapencaine [INN]

Preferred Name

English

TRAPENCAINE

Official Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29701