PENTAMORPHONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28N2O3
Molecular Weight	368.4693
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCN[C@]12C=CC(=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4O

InChI

InChIKey=NRPCWSUJMWEFOK-KDXIVRHGSA-N

InChI=1S/C22H28N2O3/c1-3-4-5-11-23-22-9-8-16(26)20-21(22)10-12-24(2)17(22)13-14-6-7-15(25)19(27-20)18(14)21/h6-9,17,20,23,25H,3-5,10-13H2,1-2H3/t17-,20+,21+,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H28N2O3
Molecular Weight	368.4693
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1708214 | https://www.ncbi.nlm.nih.gov/pubmed/1698039 | https://www.ncbi.nlm.nih.gov/pubmed/2465708

Pentamorphone was developed as a highly potent opioid with rapid onset and short duration of action that has been reported to produce analgesia with limited depression of ventilation. Pentamorphone participated in a clinical trial for the management of postoperative pain. However, no acute cardiorespiratory changes were observed. The drug was ineffective for treating acute postoperative pain after major surgery. In addition, was shown that pentamorphone, 10 micrograms/kg, does not seem to offer any significant advantage over opioids currently used for anesthesia in patients undergoing elective coronary artery bypass grafting (CABG). That is why its further development was discontinued.

Approval Year

PubMed

Title	Date	PubMed
A comparison of pentamorphone and fentanyl in balanced anaesthesia during general surgery.	1994-08	7522977
Pharmacodynamics of pentamorphone during coronary artery bypass grafting in humans.	1992-04	1373660
Depression of ventilatory responses to hypoxia and hypercapnia after pentamorphone.	1990-10	1698039
Cardiovascular effects of large doses of pentamorphone in the dog.	1990-06	1720033
Evaluation of pentamorphone in humans: a new potent opiate.	1989-03	2465708

Sample Use Guides

In Vivo Use Guide

double-blind study of 72 patients given 0.08, 0.16, or 0.24 micrograms/kg of pentamorphone or a placebo intravenously in the recovery room after major abdominal or orthopedic surgery.

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:52:20 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:20 GMT 2025`
Record UNII	MM4487B4MW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

A-4492

Preferred Name

English

PENTAMORPHONE

Official Name

English

14B-N-PENTYLAMINOMORPHINONE

Common Name

English

MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5-EPOXY-3-HYDROXY-17-METHYL-14-(PENTYLAMINO)-, (5.ALPHA.)-

Systematic Name

English

PENTAMORPHONE [MART.]

Common Name

English

pentamorphone [INN]

Common Name

English

RX77989

Code

English

PENTAMORPHONE [USAN]

Common Name

English

RX-77989

Code

English

Code System Code Type Description

PUBCHEM

5464186