U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C22H27NO
Molecular Weight 321.4559
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENAZOCINE

SMILES

C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CCC4=CC=CC=C4

InChI

InChIKey=ZQHYKVKNPWDQSL-KNXBSLHKSA-N
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/t16-,21+,22+/m0/s1

HIDE SMILES / InChI
(-)-Phenazocine is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects. (-)-Phenazocine is a potent mu opioid receptor agonist. In addition, (−)-phenazocine is also known to bind to δ opioid receptors (DOR) and κ opioid receptors (KOR). Regarding their analgesic potency, (−)-phenazocine was twenty times more potent than morphine in the hot plate test and sixty times more potent than its dextro enantiomer when it was subcutaneously (s.c.) administered

Approval Year

Doses

Doses

DosePopulationAdverse events​
6 mg single, intramuscular
Highest studied dose
Dose: 6 mg
Route: intramuscular
Route: single
Dose: 6 mg
Sources: Page: p.338
unhealthy
Health Status: unhealthy
Condition: Chronic pain due to cancer
Sources: Page: p.338
PubMed

PubMed

TitleDatePubMed
The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse.
2001 Apr 13
MS-377, a selective sigma receptor ligand, indirectly blocks the action of PCP in the N-methyl-D-aspartate receptor ion-channel complex in primary cultured rat neuronal cells.
2002 Feb 22
Antagonism of NMDA receptors by sigma receptor ligands attenuates chemical ischemia-induced neuronal death in vitro.
2002 Nov 29
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.
2003 Oct
Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats.
2004 Aug 6
Phenytoin differentially modulates the affinity of agonist and antagonist ligands for sigma 1 receptors of guinea pig brain.
2005 Mar 1
Sigma-1 receptors bind cholesterol and remodel lipid rafts in breast cancer cell lines.
2007 Dec 1
sigma(2)-receptor ligand-mediated inhibition of inwardly rectifying K(+) channels in the heart.
2007 Jul
Voltage-gated sodium channel modulation by sigma-receptors in cardiac myocytes and heterologous systems.
2009 May
Patents

Patents

Name Type Language
PHENAZOCINE
INN   MI   WHO-DD  
INN  
Official Name English
phenazocine [INN]
Common Name English
Phenazocine [WHO-DD]
Common Name English
PHENAZOCINE [MI]
Common Name English
PHENETHYLAZOCINE
Common Name English
(±)-.ALPHA.-PHENAZOCINE
Common Name English
2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(2-PHENYLETHYL)-
Systematic Name English
PHENAZOCINE CIS-(±)-FORM [MI]
Common Name English
PHENOBENZORPHAN
Common Name English
IDS-NP-008
Code English
2'-HYDROXY-5,9-DIMETHYL-2-PHENETHYL-6,7-BENZOMORPHAN
Common Name English
Classification Tree Code System Code
WHO-VATC QN02AD02
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
DEA NO. 9715
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
WHO-ATC N02AD02
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
NCI_THESAURUS C67413
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
Code System Code Type Description
DRUG BANK
DB13606
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
SMS_ID
100000082210
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID90860736
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
FDA UNII
J0ND6N0AQC
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
WIKIPEDIA
PHENAZOCINE
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL46399
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
RXCUI
8119
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY RxNorm
EVMPD
SUB09752MIG
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
PUBCHEM
443405
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
CAS
127-35-5
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
204-835-3
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
NCI_THESAURUS
C96728
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
INN
900
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
MERCK INDEX
m8602
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
2119
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
CAS
58073-76-0
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY
MESH
D010620
Created by admin on Sat Dec 16 16:45:41 UTC 2023 , Edited by admin on Sat Dec 16 16:45:41 UTC 2023
PRIMARY