Levallorphan - CAS 152-02-3
Catalog number:
152-02-3
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C19H25NO
Molecular Weight:
283.41
COA:
Inquire
Targets:
Opioid Receptor
Description:
Levallorphan, an allylmorphinan derivative, has been found to be a μ-opioid receptor antagonist that could be an analgesic agent as an prescription drug.
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Purity:
98%
Appearance:
Powder
Synonyms:
levallorphan;(-)-3-Hydroxy-N-allylmorphinan;17-Allylmorphinan-3-ol;2H-10,4a-Iminoethanophenanthren-6-ol, 11-allyl-1,3,4,9,10,10a-hexahydro- (6CI);l-N-Allyl-3-hydroxymorphinan;MCL 113
Storage:
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
MSDS:
Inquire
Quality Standard:
In-house standard
Quantity:
Milligram-Grams
Boiling Point:
433.5ºC at 760mmHg
Density:
1.14 g/cm3
InChIKey:
OZYUPQUCAUTOBP-QXAKKESOSA-N
InChI:
InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1
Canonical SMILES:
C=CCN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O
1.Inhibition of morphine-induced cAMP overshoot: a cell-based assay model in a high-throughput format.
Xia M1, Guo V, Huang R, Shahane SA, Austin CP, Nirenberg M, Sharma SK. Cell Mol Neurobiol. 2011 Aug;31(6):901-7. doi: 10.1007/s10571-011-9689-y. Epub 2011 May 20.
Opiates are not only potent analgesics but also drugs of abuse mainly because they produce euphoria. Chronic use of opiates results in the development of tolerance and dependence. Dr Marshall Nirenberg's group at the National Institutes of Health (NIH) was the first to use a cellular model system of Neuroblastoma × Glioma hybrid cells (NG108-15) to study morphine addiction. They showed that opiates affect adenylyl cyclase (AC) by two opposing mechanisms mediated by the opiate receptor. Although the cellular mechanisms that cause addiction are not yet completely understood, the most observed correlative biochemical adaptation is the upregulation of AC. This model also provides the opportunity to look for compounds which could dissociate the acute effect of opiates from the delayed response, upregulation of AC, and thus lead to the discovery of non-addictive drugs. To identify small molecule compounds that can inhibit morphine-induced cAMP overshoot, we have validated and optimized a cell-based assay in a high throughput format that measures cellular cAMP production after morphine withdrawal.
2.Sensitive determination of pentazocine in human tissues by high-performance liquid chromatography.
Imamura T1, Kudo K, Namera A, Yashiki M, Kojima T. Leg Med (Tokyo). 2000 Aug;2(2):119-22.
The authors developed a simple, reliable and sensitive method for the determination of pentazocine in human solid tissues using high-performance liquid chromatography, combined with a three-step liquid-liquid extraction procedure. Levallorphan tartrate served as the internal standard. The extract was evaporated to dryness and dissolved in the mobile phase of acetonitrile/10 mM phosphate buffer (pH 4.0). The eluent was pumped at a flow rate of 0.4 ml/min through a Spherisorb Ph (2.1 mm I.D. x 150 mm) column. A fluorescence detector with excitation at 247 nm and emission at 320 nm was used. The lower limit of detection was about 0.5 ng/g. The calibration curve was linear over the concentration ranges from 1 to 500 ng/g in each tissue examined and could be determined up to at least 10.0 microg/g by means of reduction of injected volumes. Using this method, the concentrations of pentazocine could be determined in the tissues of an autopsied individual for toxicological evaluation.
3.Effects of opioids in morphine-treated pigeons trained to discriminate among morphine, the low-efficacy agonist nalbuphine, and saline.
Walker EA1, Picker MJ, Granger A, Dykstra LA. J Pharmacol Exp Ther. 2004 Jul;310(1):150-8. Epub 2004 Mar 25.
In opioid-dependent subjects, the low-efficacy mu agonist nalbuphine generally precipitates withdrawal or withdrawal-like stimulus effects. To provide a more complete characterization of the discriminative stimulus effects of nalbuphine in opioid-treated subjects, seven White Carneux pigeons were treated daily with 10 mg/kg morphine i.m. and trained 6 h later to discriminate among 10 mg/kg morphine, 1.0 mg/kg nalbuphine, and saline by responding on one of three different keys. When tested, morphine produced morphine-key responding and nalbuphine produced nalbuphine-key responding. Replacing the daily morphine injection with saline produced nalbuphine-key responding, and this effect was reversed by the administration of morphine. In substitution tests with other compounds, the antagonists naltrexone (i.m.) and CTAP (D-Phe-Cys-Tyr-D-Tryp-Lys-Thr-Pen-Thr-NH2) (i.c.v.) produced nalbuphine-key responding. High-efficacy agonists fentanyl and etorphine produced morphine-key responding.
4.In rats, acute morphine dependence results in antagonist-induced response suppression of intracranial self-stimulation.
Easterling KW1, Holtzman SG. Psychopharmacology (Berl). 2004 Sep;175(3):287-95.
RATIONALE: Lower (0.001-1.0 mg/kg) doses of the opioid antagonist naltrexone produce few behavioral effects in otherwise drug-free rats responding for ICSS, but reduce response rates by up to 75% after a single dose of morphine.
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Chemical Structure

CAS 152-02-3 Levallorphan

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