ENADOLINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H32N2O3.ClH
Molecular Weight	432.983
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)CC4=CC=CC5=C4C=CO5

InChI

InChIKey=ZVVAINSYJGRDTR-TYLGTTGKSA-N

InChI=1S/C24H32N2O3.ClH/c1-25(23(27)16-18-6-4-7-22-19(18)9-15-28-22)20-8-11-24(10-5-14-29-24)17-21(20)26-12-2-3-13-26;/h4,6-7,9,15,20-21H,2-3,5,8,10-14,16-17H2,1H3;1H/t20-,21-,24-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C24H32N2O3
Molecular Weight	396.5225
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/2178014 | https://www.ncbi.nlm.nih.gov/pubmed/8889289 | https://www.ncbi.nlm.nih.gov/pubmed/15989506

Enadoline (CI-977) is a potent and selective agonist at the kappa-opioid receptor. Enadoline is a potent antinociceptive agent. Clinical use of enadoline was associated with dose-limiting neuropsychiatric adverse events. Enadoline may yet find some application against ischaemic stroke and severe head injury, presumably in comatose patients.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Design and synthesis of novel dimeric morphinan ligands for kappa and micro opioid receptors.	2003-11-20	14613319
Analysis of [3H]bremazocine binding in single and combinatorial opioid receptor knockout mice.	2001-03-02	11239918
Radioligand-dependent discrepancy in agonist affinities enhanced by mutations in the kappa-opioid receptor.	1996-10	8863844
CI-977, a novel and selective agonist for the kappa-opioid receptor.	1990-09	2178014

Sample Use Guides

In Vivo Use Guide

20, 40, 80, and 160 microg/70 kg. The highest dose (160 microg/70 kg) was not tolerated and led to psychotomimetic effects.

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:37 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:37 GMT 2025`
Record UNII	086I9HO04E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENADOLINE HYDROCHLORIDE

Official Name

English

CI-977

Preferred Name

English

ENADOLINE HYDROCHLORIDE [USAN]

Common Name

English

4-BENZOFURANACETAMIDE, N-METHYL-N-(7-(1-PYRROLIDINYL)-1-OXASPIRO(4.5)DEC-8-YL)-, MONOHYDROCHLORIDE, (5R-(5.ALPHA.,7.ALPHA,8.BETA.))-

Common Name

English

ENADOLINE HYDROCHLORIDE [MART.]

Common Name

English

N-Methyl-N-[(5R,7S,8S)-7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-4-benzofuranacetamide monohydrochloride

Systematic Name

English

ENADOLINE HCL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413