Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H29NO2 |
| Molecular Weight | 315.4498 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@]12CCN(CC3(O)CC3)[C@H](CC4=CC=C(O)C=C14)C2(C)C
InChI
InChIKey=ZDXGFIXMPOUDFF-XLIONFOSSA-N
InChI=1S/C20H29NO2/c1-4-20-9-10-21(13-19(23)7-8-19)17(18(20,2)3)11-14-5-6-15(22)12-16(14)20/h5-6,12,17,22-23H,4,7-11,13H2,1-3H3/t17-,20+/m1/s1
| Molecular Formula | C20H29NO2 |
| Molecular Weight | 315.4498 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Bremazocine, a kappa-opioid agonist has limited potential as a clinical analgesic, however, possesses a possible utility for the therapy of alcohol and drug addiction. It was shown that bremazocine-like drugs could lower intraocular pressure and to minimize ischemic damage, that could be used in the therapy of glaucoma and cardiovascular disease.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A new synthesis of 2,3-di- or 2,3,3-trisubstituted 2,3-dihydro-4-pyridones by reaction of 3-ethoxycyclobutanones and N-p-toluenesulfonyl imines using titanium(IV) chloride: synthesis of (+/-)-bremazocine. | 2010-07-16 |
|
| Standard opioid agonists activate heteromeric opioid receptors: evidence for morphine and [d-Ala(2)-MePhe(4)-Glyol(5)]enkephalin as selective μ-δ agonists. | 2010-02-17 |
|
| Central antinociception induced by mu-opioid receptor agonist morphine, but not delta- or kappa-, is mediated by cannabinoid CB1 receptor. | 2009-09 |
|
| Effects of atypical kappa-opioid receptor agonists on intrathecal morphine-induced itch and analgesia in primates. | 2009-01 |
|
| Engineered G-protein Coupled Receptors are Powerful Tools to Investigate Biological Processes and Behaviors. | 2009 |
|
| Acute delta- and kappa-opioid agonist pretreatment potentiates opioid antagonist-induced suppression of water consumption. | 2008-08-15 |
|
| The mu-opioid receptor agonist morphine, but not agonists at delta- or kappa-opioid receptors, induces peripheral antinociception mediated by cannabinoid receptors. | 2008-07 |
|
| Pharmacological selectivity of CTAP in a warm water tail-withdrawal antinociception assay in rats. | 2008-01 |
|
| Selectivity of delta- and kappa-opioid ligands depends on the route of central administration in mice. | 2007-07 |
|
| Biological targets for isatin and its analogues: Implications for therapy. | 2007-06 |
|
| Aqueous humor dynamics in monkeys in response to the kappa opioid agonist bremazocine. | 2007 |
|
| Ligands regulate cell surface level of the human kappa opioid receptor by activation-induced down-regulation and pharmacological chaperone-mediated enhancement: differential effects of nonpeptide and peptide agonists. | 2006-11 |
|
| New kappa opioid receptor from zebrafish Danio rerio. | 2006-09-11 |
|
| Characterization of opioid-binding sites in zebrafish brain. | 2006-02 |
|
| Interaction of bivalent ligand KDN21 with heterodimeric delta-kappa opioid receptors in human embryonic kidney 293 cells. | 2005-10 |
|
| Purification and mass spectrometric analysis of the delta opioid receptor. | 2005-05-20 |
|
| BU74, a complex oripavine derivative with potent kappa opioid receptor agonism and delayed opioid antagonism. | 2005-02-21 |
|
| Reciprocal regulation of agonist and inverse agonist signaling efficacy upon short-term treatment of the human delta-opioid receptor with an inverse agonist. | 2005-01 |
|
| Bremazocine: a kappa-opioid agonist with potent analgesic and other pharmacologic properties. | 2005 |
|
| Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine. | 2004-06-28 |
|
| Differential effects of bremazocine on oral phencyclidine (PCP) self-administration in male and female rhesus monkeys. | 2004-05 |
|
| Bremazocine increases C-type natriuretic peptide levels in aqueous humor and enhances outflow facility. | 2004-05 |
|
| Peripheral selectivity and apparent efficacy of dynorphins: comparison to non-peptidic kappa-opioid agonists in rhesus monkeys. | 2004-04 |
|
| Kappa-opioid receptors are differentially labeled by arylacetamides and benzomorphans. | 2004-02-06 |
|
| Variable modulation of opioid brain uptake by P-glycoprotein in mice. | 2004-01-15 |
|
| A novel and facile preparation of bremazocine enantiomers through optically pure N-norbremazocines. | 2004-01-02 |
|
| Opioid interactions in rhesus monkeys: effects of delta + mu and delta + kappa agonists on schedule-controlled responding and thermal nociception. | 2003-12 |
|
| Purification and mass spectrometric analysis of the mu opioid receptor. | 2003-10-21 |
|
| Ultra-long antagonism of kappa opioid agonist-induced diuresis by intracisternal nor-binaltorphimine in monkeys. | 2003-08-22 |
|
| Involvement of glutamate and gamma-amino-butyric acid receptor systems on gastric acid secretion induced by activation of kappa-opioid receptors in the central nervous system in rats. | 2003-03 |
|
| The kappa-opioid agonist (+/-)-bremazocine elicits peripheral antinociception by activation of the L-arginine/nitric oxide/cyclic GMP pathway. | 2002-11-01 |
|
| Autoradiography of opioid and ORL1 ligands in opioid receptor triple knockout mice. | 2002-11 |
|
| Comparison of the discriminative and neuroendocrine effects of centrally penetrating kappa-opioid agonists in rhesus monkeys. | 2002-10 |
|
| Effect of bremazocine, a kappa-opioid receptor agonist, on inositol phosphate formation in isolated iris-ciliary bodies. | 2002-10 |
|
| Quantitative autoradiographic mapping of opioid receptors in the brain of delta-opioid receptor gene knockout mice. | 2002-07-26 |
|
| Effects of bremazocine on self-administration of smoked cocaine base and orally delivered ethanol, phencyclidine, saccharin, and food in rhesus monkeys: a behavioral economic analysis. | 2002-06 |
|
| Elevation of atrial natriuretic peptide levels in aqueous humor of the rabbit by kappa opioid receptor agonists. | 2002-05-29 |
|
| Motivational effects mu- and kappa-opioid agonists following acute and chronic restraint stress: involvement of dopamine D(1) and D(2) receptors. | 2002-05-14 |
|
| Inhibition of mu and delta opioid receptor ligand binding by the peptide aldehyde protease inhibitor, leupeptin. | 2002-04-15 |
|
| Sex and rat strain determine sensitivity to kappa opioid-induced antinociception. | 2002-03 |
|
| Short-term inverse-agonist treatment induces reciprocal changes in delta-opioid agonist and inverse-agonist binding capacity. | 2001-10 |
|
| Biphasic alterations of cAMP levels and inhibition of norepinephrine release in iris-ciliary body by bremazocine. | 2001-09 |
|
| Effects of kappa-opioid receptor agonists on long-term cocaine use and dopamine neurotransmission. | 2001-08-24 |
|
| Kappa opioid agonists alter dopamine markers and cocaine-stimulated locomotor activity. | 2001-07 |
|
| Stimulatory effects of centrally injected kappa-opioid receptor agonists on gastric acid secretion in urethane-anesthetized rats. | 2001-04-27 |
|
| Opioid receptors on bone marrow neutrophils modulate chemotaxis and CD11b/CD18 expression. | 2001-03-02 |
|
| Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. | 1998-03 |
|
| Differential effects of fedotozine compared to other kappa agonists on diuresis in rats. | 1996-12 |
|
| Cloning and functional comparison of kappa and delta opioid receptors from mouse brain. | 1993-07-15 |
|
| Synthesis and evaluation of N-substituted cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamines as high affinity sigma receptor ligands. Identification of a new class of highly potent and selective sigma receptor probes. | 1990-11 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 17:49:06 GMT 2025
by
admin
on
Wed Apr 02 17:49:06 GMT 2025
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| Record UNII |
FDR3CJ69GC
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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DTXSID001317125
Created by
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FDR3CJ69GC
Created by
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443406
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75684-07-0
Created by
admin on Wed Apr 02 17:49:06 GMT 2025 , Edited by admin on Wed Apr 02 17:49:06 GMT 2025
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| Related Record | Type | Details | ||
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TARGET -> AGONIST |
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AGONIST -> TARGET |
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RACEMATE -> ACTIVE ENANTIOMER |
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