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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 of .ALPHA.-NALOXOL

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
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

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

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence.
2001 Jun
Patents

Patents

Sample Use Guides

rats: 0.05–100 mg/kg, s.c.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 16:24:44 UTC 2023
Edited
by admin
on Thu Jul 06 16:24:44 UTC 2023
Record UNII
FLW43Q2H9L
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Thu Jul 06 16:24:44 UTC 2023 , Edited by admin on Thu Jul 06 16:24:44 UTC 2023
PRIMARY
PUBCHEM
5492271
Created by admin on Thu Jul 06 16:24:44 UTC 2023 , Edited by admin on Thu Jul 06 16:24:44 UTC 2023
PRIMARY
WIKIPEDIA
Naloxol
Created by admin on Thu Jul 06 16:24:44 UTC 2023 , Edited by admin on Thu Jul 06 16:24:44 UTC 2023
PRIMARY
MERCK INDEX
M11769
Created by admin on Thu Jul 06 16:24:44 UTC 2023 , Edited by admin on Thu Jul 06 16:24:44 UTC 2023
PRIMARY
SMS_ID
300000013056
Created by admin on Thu Jul 06 16:24:44 UTC 2023 , Edited by admin on Thu Jul 06 16:24:44 UTC 2023
PRIMARY
CAS
20410-95-1
Created by admin on Thu Jul 06 16:24:44 UTC 2023 , Edited by admin on Thu Jul 06 16:24:44 UTC 2023
PRIMARY
FDA UNII
FLW43Q2H9L
Created by admin on Thu Jul 06 16:24:44 UTC 2023 , Edited by admin on Thu Jul 06 16:24:44 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
PARENT -> METABOLITE LESS ACTIVE
Results also indicate that delay in onset of action of 6-alpha-naloxol at opioid receptors in the central nervous system may contribute significantly to its reduced potency relative to naloxone under certain morphine pretreatment conditions.
PARENT -> METABOLITE
URINE