Noscapine - CAS 128-62-1

Noscapine - CAS 128-62-1 Catalog number: BADC-00302

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Noscapine is often used as an antitussive medication.

Category
ADCs Cytotoxin
Product Name
Noscapine
CAS
128-62-1
Catalog Number
BADC-00302
Molecular Formula
C22H23NO7
Molecular Weight
413.42
Noscapine

Ordering Information

Catalog Number Size Price Quantity
BADC-00302 -- $--
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Description
Noscapine is often used as an antitussive medication.
Synonyms
CB-3304; CB 3304; CB3304; alpha-Narcotine; Narcompren; Tusscapine; Narcosine; Terbenol; Opianin; Capval
IUPAC Name
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Canonical SMILES
CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
InChI
InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1
InChIKey
AKNNEGZIBPJZJG-MSOLQXFVSA-N
Density
1.395
Solubility
Chloroform, not in water
Melting Point
174-176 °C.
Optical Rotation
MAX ABSORPTION (ETHANOL): 209, 291, 309-310 NM (LOG E= 4.86, 3.60, 3.69); SPECIFIC OPTICAL ROTATION: +32.7 at 33 °C/D (WATER, 4.56%)
Mechanism Of Action
Noscapine's antitussive effects appear to be primarily mediated by its sigma receptor agonist activity. Evidence for this mechanism is suggested by experimental evidence in rats. Pretreatment with rimcazole, a sigma specific antagonist, causes a dose-dependent reduction in antitussive activity of noscapine.
In Vitro
Noscapine reduced clonogenic survival without enhancement of radiosensitivity in vitro. Noscapine combined with radiation significantly increased tumor growth delay: 5, 8, 13, and 18 days for control, noscapine alone, radiation alone, and the combination treatment, respectively (p < 0.001). To assess the effect of the combination of noscapine plus radiation on the tumor vasculature, tubule formation by the murine endothelial 2H11 cells was tested. Noscapine with radiation significantly inhibited tubule formation compared with radiation alone. By immunohistochemistry, tumors treated with the combination of noscapine plus radiation showed a decrease in BrdU incorporation, an increase in apoptosis by terminal deoxynucleotidyl transferase-mediated deoxyuridine triphosphate nick end labeling, and a decrease in tumor vessel density compared with tumors treated with radiation alone.
In Vivo
Noscapine (4 μM) significantly attenuated intracellular Ca(2+) elevation (P < 0.001). Also, noscapine significantly decreased NO production during a 30-minute oxygen-glucose deprivation/reperfusion (P < 0.01). The inhibitory effect of noscapine (4 μM) on intracellular Ca(2+) was greater than ionotropic glutamate receptors antagonists. Noscapine is protective against ischemia/reperfusion-induced excitotoxic injury in OLN-93 oligodendrocyte. This protective effect seems to be related to attenuation of intracellular Ca(2+) overload and NO production.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT00912899Refractory Multiple MyelomaPhase 12016-10-07Cougar Biotechnology, Inc.Terminated (Terminated early due to lack of clinical response.)
NCT00183950Non-Hodgkin's LymphomaPhase 1, Phase 22014-05-22University of Southern CaliforniaTerminated (No funding)
Application
ADCs Cytotoxin
Appearance
White Solid
Purity
98 % (TLC).
Shelf Life
Sublimes @ 150-160 °C;Very Weak Base Forming Unstable Salts With Acids & Strong Bases; Salts Formed With Acids Are Unstable In Water;Stable In Light & Air
Shipping
-20°C (International: -20°C)
Storage
Store at +4 °C, in dark place.
Pictograms
Irritant
Signal Word
Warning
Current Developer
Cougar Biotechnology, Inc
1. Determination of Noscapine and Papaverine in Mixtures
Neelam Khanna, lshivar C. Varshney, Sadhana Banerjee* and Bajsang B. Singh. Analyst, Vol. 108
Noscapine was extracted with 20-, 10-, 10- and 5-ml portions of 4% sodium hydroxide solution. To the combined aqueous solution were added 10 ml of concentrated hydrochloric acid and the resulting acidic solution was transferred into a separating funnel and then rinsed with three successive 5-ml portions of water. About 10 ml of concentrated ammonia solution (27.0-30.0% m/V of ammonia, ca. 0.896 g ml-1) were added and the mixture was extracted with successive 20-, lo-, 10- and 5-ml portions of chloroform, washing each extract with the same 10ml of water. The chloroform extract was dried over anhydrous sodium sulphate, filtered, the sodium sulphate washed twice with 5 ml of chloroform, the washings were added to the extract, the solvent was distilled off and the contents were evaporated to dryness on a water-bath. The residue was dissolved in 10 ml of glacial acetic acid, 5 ml of acetic anhydride were added and the solution was titrated against 0.1 N perchloric acid using crystal violet as the indicator, the colour change being from violet to green. Each 1 ml of 0.1 N perchloric acid is equivalent to 0.04134 g of noscapine.
2. A high-throughput multi-class liquid chromatography tandem mass spectrometry method for quantitative determination of licit and illicit drugs in whole blood
Lambert K. Sørensen* and Jørgen B. Hasselstrøm. Anal. Methods, 2013, 5, 3185–3193
Calibrants based on blank donor blood from single persons were used for the construction of 5- to 6-point calibration curves. The samples were treated according to the same procedure except that 100 mL ofMeOH was replaced by 100 mLof the mixed standards of the drug substances. Concentrations in the original blood sample of 10, 100, 400, 800, 1200 and 1600 mg L-1 for chlordiazepoxide, citalopram, lidocaine, methadone, tramadol and O-desmethyltramadol; 2, 8, 16, 24 and 32 mg L-1for buprenorphine, norbuprenorphine, fentanyl, 6-MAM, noscapine, THC and THC-OH; 5, 20, 40, 60 and 80 mg L-1 for THC-COOH; and 5, 50, 200, 400, 600 and 800 mg L-1of the remaining substances were obtained. The SIL analogues were used in the quantification of all substances except noscapine and desmethylmirtazapine because SIL analogues of these substances were not commercially available at the time of the study. Instead, zolpidem-D6 andmirtazapine-D3 were used as IS for noscapine and desmethyl-mirtazapine, respectively.
3. Detection of drugs in latent fingermarks by mass spectrometric methods
Angelina Yimei Lim,* Frederick Rowell, Cheryl Grace Elumbaring-Salazar, Jason Lokee and Jan Ma. Anal. Methods, 2013, 5, 4378–4385
Redevelopment of pre-dusted (using Lightning silver/grey magnetic fingerprint powder) spiked lifted fingermarks by either re-dusting with silica-CB particles or spraying with silica-CB particle suspension resulted in the successful SALDI-MS detection of nicotine, noscapine and 6-MAM. Fig. 6 shows the SALDI-MS detection of noscapine at m/z 220 post-redevelopment. The noscapine peak was initially absent in the pre-dusted fingermark. Heroin was detected in the sprayed section of thefingermark as [M + Na]+ at m/z 392 but remained undetectable in the re-dusted section of the fingermark. It was observed that methadone did not require a matrix for SALDI-MS and could be detected in the Lightning silver/grey dusted lifted fingermark. Also, it was noted that redevelopment with silica-CB particles using either method did not improve the S/N value of the peak of interest for methadone.
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