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
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
| Molecular Formula | C22H27NO |
| Molecular Weight | 321.4559 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
(-)-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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2009-12 |
|
| Voltage-gated sodium channel modulation by sigma-receptors in cardiac myocytes and heterologous systems. | 2009-05 |
|
| Sigma1 receptor antagonists determine the behavioral pattern of the methamphetamine-induced stereotypy in mice. | 2009-05 |
|
| Sigma-1 receptor regulation of voltage-gated calcium channels involves a direct interaction. | 2008-11 |
|
| sigma-1 receptors protect RGC-5 cells from apoptosis by regulating intracellular calcium, Bax levels, and caspase-3 activation. | 2008-06 |
|
| Combination of virtual screening and high throughput gene profiling for identification of novel liver X receptor modulators. | 2008-04-10 |
|
| Sigma-1 receptors bind cholesterol and remodel lipid rafts in breast cancer cell lines. | 2007-12-01 |
|
| Inhibition of hyperpolarization-activated cation currents by phencyclidine and some sigma ligands in rat hippocampal CA1 pyramidal neurons in vitro. | 2007-09 |
|
| sigma(2)-receptor ligand-mediated inhibition of inwardly rectifying K(+) channels in the heart. | 2007-07 |
|
| Involvement of the sigma1 receptor in inhibiting activity of fluvoxamine on marble-burying behavior: comparison with paroxetine. | 2007-06-01 |
|
| Effects of (+)SKF 10047, a sigma-1 selective agonist, on isolation-induced aggression in male mice. | 2006-11 |
|
| Phenytoin differentially modulates the affinity of agonist and antagonist ligands for sigma 1 receptors of guinea pig brain. | 2005-03-01 |
|
| Age-related expression of sigma1 receptors and antidepressant efficacy of a selective agonist in the senescence-accelerated (SAM) mouse. | 2005-02-15 |
|
| Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats. | 2004-08-06 |
|
| Dimemorfan enhances acetylcholine release from rat hippocampal slices. | 2004-05-15 |
|
| [Stimulation of the delta 1-receptors help to decrease reperfusion induced myocardial stunning]. | 2004-05-11 |
|
| Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine. | 2004-04 |
|
| Enhanced antidepressant efficacy of sigma1 receptor agonists in rats after chronic intracerebroventricular infusion of beta-amyloid-(1-40) protein. | 2004-02-20 |
|
| Antitussive activity of sigma-1 receptor agonists in the guinea-pig. | 2004-01 |
|
| Characterization of phenothiazine-induced apoptosis in neuroblastoma and glioma cell lines: clinical relevance and possible application for brain-derived tumors. | 2004 |
|
| Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice. | 2003-10 |
|
| Anti-amnesic effect of dimemorfan in mice. | 2003-03 |
|
| Activity of opioid ligands in cells expressing cloned mu opioid receptors. | 2003-01-04 |
|
| Antagonism of NMDA receptors by sigma receptor ligands attenuates chemical ischemia-induced neuronal death in vitro. | 2002-11-29 |
|
| Effects of sigma(1) receptor ligand MS-377 on D(2) antagonists-induced behaviors. | 2002-10 |
|
| Strain differences in sigma(1) receptor-mediated behaviours are related to neurosteroid levels. | 2002-05 |
|
| The sigma receptor as a ligand-regulated auxiliary potassium channel subunit. | 2002-04-25 |
|
| 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. | 2002-02-22 |
|
| Receptor mechanisms and circuitry underlying NMDA antagonist neurotoxicity. | 2002 |
|
| 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. | 2001-12 |
|
| Modulation of dopamine uptake in rat nucleus accumbens: effect of specific dopamine receptor antagonists and sigma ligands. | 2001-10-26 |
|
| The antidepressant-like effect induced by sigma(1)-receptor agonists and neuroactive steroids in mice submitted to the forced swimming test. | 2001-09 |
|
| Involvement of the sigma receptor in passive-avoidance learning in the day-old chick during the second wave of neuronal activity. | 2001-05 |
|
| The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse. | 2001-04-13 |
|
| Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors. | 2001-04 |
|
| Oral pentazocine and phenazocine: a comparison in postoperative pain. | 1971-05 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 08:21:14 GMT 2025
by
admin
on
Wed Apr 02 08:21:14 GMT 2025
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| Record UNII |
J0ND6N0AQC
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Validated (UNII)
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WHO-VATC |
QN02AD02
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DEA NO. |
9715
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WHO-ATC |
N02AD02
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NCI_THESAURUS |
C67413
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DB13606
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100000082210
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DTXSID90860736
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J0ND6N0AQC
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PHENAZOCINE
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CHEMBL46399
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8119
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SUB09752MIG
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127-35-5
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NON-SPECIFIC STEREOCHEMISTRY | |||
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204-835-3
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C96728
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900
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m8602
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2119
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58073-76-0
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D010620
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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ACTIVE MOIETY |
