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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

Description

(-)-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

1959
138
Doses

Doses

DosePopulationAdverse events​
6 mg single, intramuscular
Highest studied dose
Dose: 6 mg
Route: intramuscular
Route: single
Dose: 6 mg
Sources:
https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf
Page: p.338
unhealthy
Health Status: unhealthy
Condition: Chronic pain due to cancer
Sources:
https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf
Page: p.338
Sources:
https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf
Page: p.338
Sourcing

Sourcing

Vendor/AggregatorIDURL
Compound Cloud
443405
Toronto Research Chemicals
P295400
ZINC
ZINC000001481896
http://zinc15.docking.org/substances/ZINC000001481896
PubMed

PubMed

TitleDatePubMed
Oral pentazocine and phenazocine: a comparison in postoperative pain.
1971 May
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.
2001 Apr
The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse.
2001 Apr 13
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
Effects of sigma(1) receptor ligand MS-377 on D(2) antagonists-induced behaviors.
2002 Oct
Activity of opioid ligands in cells expressing cloned mu opioid receptors.
2003 Jan 4
Anti-amnesic effect of dimemorfan in mice.
2003 Mar
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.
2003 Oct
Characterization of phenothiazine-induced apoptosis in neuroblastoma and glioma cell lines: clinical relevance and possible application for brain-derived tumors.
2004
Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine.
2004 Apr
Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats.
2004 Aug 6
Enhanced antidepressant efficacy of sigma1 receptor agonists in rats after chronic intracerebroventricular infusion of beta-amyloid-(1-40) protein.
2004 Feb 20
Antitussive activity of sigma-1 receptor agonists in the guinea-pig.
2004 Jan
[Stimulation of the delta 1-receptors help to decrease reperfusion induced myocardial stunning].
2004 Mar-Apr
Dimemorfan enhances acetylcholine release from rat hippocampal slices.
2004 May 15
Age-related expression of sigma1 receptors and antidepressant efficacy of a selective agonist in the senescence-accelerated (SAM) mouse.
2005 Feb 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
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
Involvement of the sigma1 receptor in inhibiting activity of fluvoxamine on marble-burying behavior: comparison with paroxetine.
2007 Jun 1
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
The C-terminal amidated analogue of the substance P (SP) fragment SP(1-7) attenuates the expression of naloxone-precipitated withdrawal in morphine dependent rats.
2009 Dec
Voltage-gated sodium channel modulation by sigma-receptors in cardiac myocytes and heterologous systems.
2009 May
Patents

Patents

JP2005520783A
40
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 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
DEA NO. 9715
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
WHO-ATC N02AD02
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
NCI_THESAURUS C67413
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
Code System Code Type Description
DRUG BANK
DB13606
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
SMS_ID
100000082210
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID90860736
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
FDA UNII
J0ND6N0AQC
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
WIKIPEDIA
PHENAZOCINE
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL46399
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
RXCUI
8119
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY RxNorm
EVMPD
SUB09752MIG
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
PUBCHEM
443405
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
CAS
127-35-5
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
204-835-3
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
NCI_THESAURUS
C96728
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
INN
900
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
MERCK INDEX
m8602
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2119
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
CAS
58073-76-0
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
MESH
D010620
Created by admin on Sat Dec 16 16:45:41 GMT 2023 , Edited by admin on Sat Dec 16 16:45:41 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of PHENAZOCINE
SALT/SOLVATE (PARENT)
Structure of PHENAZOCINE HYDROBROMIDE
NIH
NCATS
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HHS VULNERABILITY DISCLOSURE
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