.ALPHA.-NALOXOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H23NO4
Molecular Weight	329.3902
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(CC=C)CC[C@@]14[C@@]5(O)CC[C@@H]2O)=CC=C3O

InChI

InChIKey=HMWHERQFMBEHNG-AQQQZIQISA-N

InChI=1S/C19H23NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,13-14,17,21-23H,1,5-10H2/t13-,14+,17-,18-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H23NO4
Molecular Weight	329.3902
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11413242
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19061911 | https://www.ncbi.nlm.nih.gov/pubmed/15956992

6-alpha-Naloxol is active metabolite of naloxone. 6-alpha-Naloxol was shown to be neutral antagonist at the mu receptor in vitro, with no affect on cAMP levels or GTPitalic gammaS binding, regardless of morphine pretreatment. It elicits withdrawal behaviour and conditioned place aversion in morphine pretreated rodents.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11413242	Antagonist 2778		0.63 nM [Ki]
Delta opioid receptor 77 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11413242	Antagonist 2778		2.1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence.	2001 Jun	11413242
Constitutively active micro opioid receptors mediate the enhanced conditioned aversive effect of naloxone in morphine-dependent mice.	2006 Jan	15956992
Relative potency of the opioid antagonists naloxone and 6-alpha-naloxol to precipitate withdrawal from acute morphine dependence varies with time post-antagonist.	2009 Mar	19061911

Patents

Sample Use Guides

In Vivo Use Guide

rats: 0.05–100 mg/kg, s.c.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:49:59 UTC 2023` Edited by `admin` on `Sat Dec 16 10:49:59 UTC 2023`
Record UNII	FLW43Q2H9L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

.ALPHA.-NALOXOL

Common Name

English

MORPHINAN-3,6.ALPHA.,14-TRIOL, 17-ALLYL-4,5.ALPHA.-EPOXY-

Systematic Name

English

EN-2265

Code

English

6-HYDROXYNALOXONE, (-)-

Common Name

English

6-NALOXOL, (6.ALPHA.)-

Common Name

English

MORPHINAN-3,6,14-TRIOL, 4,5-EPOXY-17-(2-PROPEN-1-YL)-, (5.ALPHA.,6.ALPHA.)-

Systematic Name

English

.ALPHA.-NALOXOL [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID20942579