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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO4.ClH
Molecular Weight 365.851
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-NALOXOL HYDROCHLORIDE

SMILES

Cl.O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC=C)[C@H]1O5

InChI

InChIKey=VFEZXRHXAKHILC-NINXOWEVSA-N
InChI=1S/C19H23NO4.ClH/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;1H/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
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

Description
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

CNS Active
4002
Curator's Comment: 6-alpha-Naloxol is CNS active in animals. No human data available.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 0.63 nM [Ki]
Antagonist
2849
 2.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Relative potency of the opioid antagonists naloxone and 6-alpha-naloxol to precipitate withdrawal from acute morphine dependence varies with time post-antagonist.
2009-03
Constitutively active micro opioid receptors mediate the enhanced conditioned aversive effect of naloxone in morphine-dependent mice.
2006-01
Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence.
2001-06
Patents

Patents

WO2004050020A2
2

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 Mon Mar 31 23:45:41 GMT 2025
Edited
by admin
on Mon Mar 31 23:45:41 GMT 2025
Record UNII
4IF1GAT6RI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EN-2265A
Preferred Name English
.ALPHA.-NALOXOL HYDROCHLORIDE
Common Name English
N-ALLYL-14-HYDROXYDIHYDROMORPHINE HYDROCHLORIDE
Common Name English
MORPHINAN-3,6,14-TRIOL, 4,5-EPOXY-17-(2-PROPENYL)-, HYDROCHLORIDE, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
6.ALPHA.-HYDROXYNALOXONE HYDROCHLORIDE
Common Name English
Code System Code Type Description
FDA UNII
4IF1GAT6RI
Created by admin on Mon Mar 31 23:45:41 GMT 2025 , Edited by admin on Mon Mar 31 23:45:41 GMT 2025
PRIMARY
CAS
34520-00-8
Created by admin on Mon Mar 31 23:45:41 GMT 2025 , Edited by admin on Mon Mar 31 23:45:41 GMT 2025
PRIMARY
SMS_ID
300000013052
Created by admin on Mon Mar 31 23:45:41 GMT 2025 , Edited by admin on Mon Mar 31 23:45:41 GMT 2025
PRIMARY
PUBCHEM
71750907
Created by admin on Mon Mar 31 23:45:41 GMT 2025 , Edited by admin on Mon Mar 31 23:45:41 GMT 2025
PRIMARY
NIH
NCATS
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