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Details

Stereochemistry RACEMIC
Molecular Formula C22H27NO.BrH
Molecular Weight 402.368
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENAZOCINE HYDROBROMIDE

SMILES

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

InChI

InChIKey=MNMGNPZLUMHSKK-BAONSNCKSA-N
InChI=1S/C22H27NO.BrH/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;1H/t16-,21+,22+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C22H27NO
Molecular Weight 321.4559
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

(-)-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
Differential involvement of the sigma(1) (sigma(1)) receptor in the anti-amnesic effect of neuroactive steroids, as demonstrated using an in vivo antisense strategy in the mouse.
2001 Dec
Involvement of the sigma receptor in passive-avoidance learning in the day-old chick during the second wave of neuronal activity.
2001 May
Modulation of dopamine uptake in rat nucleus accumbens: effect of specific dopamine receptor antagonists and sigma ligands.
2001 Oct 26
The antidepressant-like effect induced by sigma(1)-receptor agonists and neuroactive steroids in mice submitted to the forced swimming test.
2001 Sep
Receptor mechanisms and circuitry underlying NMDA antagonist neurotoxicity.
2002
The sigma receptor as a ligand-regulated auxiliary potassium channel subunit.
2002 Apr 25
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
Strain differences in sigma(1) receptor-mediated behaviours are related to neurosteroid levels.
2002 May
Antagonism of NMDA receptors by sigma receptor ligands attenuates chemical ischemia-induced neuronal death in vitro.
2002 Nov 29
Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats.
2004 Aug 6
Dimemorfan enhances acetylcholine release from rat hippocampal slices.
2004 May 15
Phenytoin differentially modulates the affinity of agonist and antagonist ligands for sigma 1 receptors of guinea pig brain.
2005 Mar 1
Effects of (+)SKF 10047, a sigma-1 selective agonist, on isolation-induced aggression in male mice.
2006 Nov
Inhibition of hyperpolarization-activated cation currents by phencyclidine and some sigma ligands in rat hippocampal CA1 pyramidal neurons in vitro.
2007 Sep
sigma-1 receptors protect RGC-5 cells from apoptosis by regulating intracellular calcium, Bax levels, and caspase-3 activation.
2008 Jun
Sigma-1 receptor regulation of voltage-gated calcium channels involves a direct interaction.
2008 Nov
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 15:06:38 UTC 2023
Edited
by admin
on Fri Dec 15 15:06:38 UTC 2023
Record UNII
C1749020IH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENAZOCINE HYDROBROMIDE
MART.   WHO-DD  
Common Name English
2'-HYDROXY-5,9-DIMETHYL-2-PHENETHYL-6,7-BENZOMORPHAN, HYDROBROMIDE
Common Name English
PHENETHYLAZOCINE BROMIDE
Systematic Name English
PHENAZOCINE HYDROBROMIDE [MART.]
Common Name English
NIH-7519
Code English
PHENAZOCINE CIS-(±)-FORM HYDROBROMIDE
MI  
Common Name English
2'-HYDROXY-5,9-DIMETHYL-2-PHENETHYL-6,7-BENZOMORPHAN, HBR
Common Name English
PRINADOL
Common Name English
NARPHEN
Brand Name English
PHENAZOCINE HBR
Common Name English
PHENAZOCINE CIS-(±)-FORM HYDROBROMIDE [MI]
Common Name English
Phenazocine hydrobromide [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
Code System Code Type Description
CAS
1239-04-9
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
214-982-5
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
RXCUI
104979
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID20872382
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
EVMPD
SUB03734MIG
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL46399
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
PUBCHEM
13501022
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
NCI_THESAURUS
C96729
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
SMS_ID
100000085699
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
CAS
70878-79-4
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
ALTERNATIVE
FDA UNII
C1749020IH
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY
MERCK INDEX
m8602
Created by admin on Fri Dec 15 15:06:38 UTC 2023 , Edited by admin on Fri Dec 15 15:06:38 UTC 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY