.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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Antagonist 2,778		0.63 nM [Ki]
Delta opioid receptor 77	Antagonist 2,778		2.1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2,578

PubMed

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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

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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
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

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Code System

Code

Type

Description

EPA CompTox

DTXSID20942579

PRIMARY

PUBCHEM

5492271

PRIMARY

WIKIPEDIA

Naloxol

PRIMARY

MERCK INDEX

m11769

PRIMARY

SMS_ID

300000013056

PRIMARY

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Related Record

Type

Details


					1PE72K8X46

MU-TYPE OPIOID RECEPTOR

TARGET -> INHIBITOR

Amount:

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Related Record

Type

Details


					36B82AMQ7N

NALOXONE

PARENT -> METABOLITE LESS ACTIVE

Comments:

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.

Amount:


					36B82AMQ7N

NALOXONE

PARENT -> METABOLITE

Qualification:

URINE

Amount:

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