PHENAZOCINE


Synonyms	IDS-NP-008 Phenazocine Phenethylazocine Phenobenzorphan
Status
Molecule Category	UNKNOWN
ATC	N02AD02
UNII	J0ND6N0AQC
EPA CompTox	DTXSID90860736


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	ZQHYKVKNPWDQSL-UHFFFAOYSA-N
Smiles	CC1C2Cc3ccc(O)cc3C1(C)CCN2CCc1ccccc1
InChI	InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H27NO
Molecular Weight	321.46
AlogP	4.16
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	3.0
Polar Surface Area	23.47
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	24.0

Reference

Journal : J. Med. Chem.

Title : Synthesis and pharmacological characterization of (+/-)-5,9 alpha-dimethyl-2-[2-(4-fluorophenyl)ethyl]-2'-hydroxy-6,7-benzomorphan (fluorophen), a ligand suitable for visualization of opiate receptors in vivo.

PubMed ID : 6313921

DOI : 10.1021/jm00365a017

Year : 1983

Volume : 26

Issue : 11

First Page : 1643

Last Page : 1645

Authors : Rice KC, Konicki PE, Quirion R, Burke TR, Pert CB.

Abstract : A fluorinated derivative of the benzomorphan opiate agonist phenazocine, (+/-)-5,9 alpha-dimethyl-2-[2-(4-fluorophenyl)ethyl]-2'-hydroxy-6, 7-benzomorphan (fluorophen), was prepared by N-acylation of (+/-)-5,9 alpha-dimethyl-2'-hydroxybenzomorphan with (p-fluorophenyl)acetyl chloride, followed by diborane reduction of the resulting amide. Fluorination produces only a twofold opiate receptor affinity loss when measured either by bioassay or receptor binding (selectivity mu congruent to delta greater than kappa). Labeled with 18F, fluorophen should be sufficiently potent to be useful as an in vivo probe for visualizing opiate receptors by positron emission transaxial tomography (PETT).

Reference

Journal : J. Med. Chem.

PubMed ID : 6313921

DOI : 10.1021/jm00365a017

Year : 1983

Volume : 26

Issue : 11

First Page : 1643

Last Page : 1645

Authors : Rice KC, Konicki PE, Quirion R, Burke TR, Pert CB.

Reference

Journal : J. Med. Chem.

PubMed ID : 6313921

DOI : 10.1021/jm00365a017

Year : 1983

Volume : 26

Issue : 11

First Page : 1643

Last Page : 1645

Authors : Rice KC, Konicki PE, Quirion R, Burke TR, Pert CB.

Reference

Journal : J. Med. Chem.

PubMed ID : 6313921

DOI : 10.1021/jm00365a017

Year : 1983

Volume : 26

Issue : 11

First Page : 1643

Last Page : 1645

Authors : Rice KC, Konicki PE, Quirion R, Burke TR, Pert CB.

Reference

Journal : J. Med. Chem.

PubMed ID : 6313921

DOI : 10.1021/jm00365a017

Year : 1983

Volume : 26

Issue : 11

First Page : 1643

Last Page : 1645

Authors : Rice KC, Konicki PE, Quirion R, Burke TR, Pert CB.

Reference

Journal : J. Med. Chem.

PubMed ID : 6313921

DOI : 10.1021/jm00365a017

Year : 1983

Volume : 26

Issue : 11

First Page : 1643

Last Page : 1645

Authors : Rice KC, Konicki PE, Quirion R, Burke TR, Pert CB.

Assay Description	Organism	Bioactivity
Ability to induce 50% of maximal effect in rabbit vas deferens expressing Opioid receptor kappa 1	Oryctolagus cuniculus	121.0 nM
Ability to induce 50% of maximal effect in mouse vas deferens expressing Opioid receptor delta 1	None	8.0 nM
Ability to induce 50% of maximal effect in guinea pig ileum expressing Opioid receptor mu 1	Cavia porcellus	9.8 nM
Ability to displace 50% of (+/-) ethylketocyclazocine (2.8) in rat brain homogenate	Rattus norvegicus	65.0 nM
Ability to displace 50% of (-) naloxone(1.0) in rat brain homogenate	Rattus norvegicus	82.0 nM
Ability to displace 50% of [3H]- labeled DADLE in rat brain homogenate	Rattus norvegicus	26.0 nM

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Cross References

Resources	Reference
ChEMBL	CHEMBL46399
DrugCentral	2119
FDA SRS	J0ND6N0AQC
PubChem	443405
SureChEMBL	SCHEMBL26733

CONTENTS

Structure
Chemical and Physical Properties
Related Entries