Details
| Stereochemistry | ABSOLUTE |
| 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 |
|---|---|---|
| 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 |
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| The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse. | 2001 Apr 13 |
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| 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 |
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| 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 |
|
| 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 |
|
| Combination of virtual screening and high throughput gene profiling for identification of novel liver X receptor modulators. | 2008 Apr 10 |
|
| 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 |
|
| 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 |
|
| Sigma1 receptor antagonists determine the behavioral pattern of the methamphetamine-induced stereotypy in mice. | 2009 May |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:56:19 GMT 2023
by
admin
on
Sat Dec 16 07:56:19 GMT 2023
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| Record UNII |
7UZW80C91Q
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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443405
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7UZW80C91Q
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DTXSID30110040
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m8602
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58640-87-2
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