Noscapine

Modify Date: 2024-01-02 19:55:11

Noscapine Structure
Noscapine structure
Common Name Noscapine
CAS Number 128-62-1 Molecular Weight 413.421
Density 1.3±0.1 g/cm3 Boiling Point 565.3±50.0 °C at 760 mmHg
Molecular Formula C22H23NO7 Melting Point 174-176ºC
MSDS N/A Flash Point 295.7±30.1 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Noscapine


Noscapine is an orally administrable drug used worldwide for cough suppression, primarily mediated by its σ-receptor agonist activity, and possess anticancer activity.Target: σ-receptorin vitro: Noscapine is a phthalideisoquinoline alkaloid from opium, is a recently discovered anticancer drug and is currently under investigation in phase-I/II clinical trials for the treatment of leukemia and lymphoma. Noscapine causes few or no side effects and has been widely used as a cough suppressant in developing countries. Noscapine has been demonstrated to interact with microtubules. Interestingly, unlike many other microtubule-targeting agents such as Paclitaxel and Nocodazole, Noscapine does not obviously affect the total amount of microtubule polymers in cells; instead, it significantly increases the time microtubules spend in the pause state. The alteration of microtubule dynamics then activates the spindle checkpoint and arrests cell cycle progression at mitosis, leading to apoptotic cell death.

 Names

Name (-)-noscapine
Synonym More Synonyms

 Noscapine Biological Activity

Description Noscapine is an orally administrable drug used worldwide for cough suppression, primarily mediated by its σ-receptor agonist activity, and possess anticancer activity.Target: σ-receptorin vitro: Noscapine is a phthalideisoquinoline alkaloid from opium, is a recently discovered anticancer drug and is currently under investigation in phase-I/II clinical trials for the treatment of leukemia and lymphoma. Noscapine causes few or no side effects and has been widely used as a cough suppressant in developing countries. Noscapine has been demonstrated to interact with microtubules. Interestingly, unlike many other microtubule-targeting agents such as Paclitaxel and Nocodazole, Noscapine does not obviously affect the total amount of microtubule polymers in cells; instead, it significantly increases the time microtubules spend in the pause state. The alteration of microtubule dynamics then activates the spindle checkpoint and arrests cell cycle progression at mitosis, leading to apoptotic cell death.
Related Catalog
References

[1]. Yang Y, et al. CYLD Regulates Noscapine Activity in Acute Lymphoblastic Leukemia via a Microtubule-Dependent Mechanism. Theranostics. 2015 Mar 2;5(7):656-666.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 565.3±50.0 °C at 760 mmHg
Melting Point 174-176ºC
Molecular Formula C22H23NO7
Molecular Weight 413.421
Flash Point 295.7±30.1 °C
Exact Mass 413.147461
PSA 75.69000
LogP 2.83
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.603
Storage condition -20℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RD2625000
CHEMICAL NAME :
Noscapine
CAS REGISTRY NUMBER :
128-62-1
BEILSTEIN REFERENCE NO. :
0099933
LAST UPDATED :
199710
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C22-H23-N-O7
MOLECULAR WEIGHT :
413.46
WISWESSER LINE NOTATION :
T C566 DO FO KN EH&&TJ HO1 K1 J- DT56 BVO DHJ HO1 IO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1520 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
853 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
960 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
725 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
83 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
73200 ug/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - convulsions or effect on seizure threshold

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
100 mg/L
REFERENCE :
ATSUDG Archives of Toxicology, Supplement. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) No.1- 1978- Volume(issue)/page/year: 4,41,1980 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84631 No. of Facilities: 1254 (estimated) No. of Industries: 2 No. of Occupations: 3 No. of Employees: 2211 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Hazard Codes Xn:Harmful;
Risk Phrases R22
Safety Phrases 24/25
RIDADR UN 1544
WGK Germany 3
RTECS RD2625000
Packaging Group III
Hazard Class 6.1(b)

 Synthetic Route

~14%

Noscapine Structure

Noscapine

CAS#:128-62-1

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 8 p. 2983 - 2987

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Noscapine Structure

Noscapine

CAS#:128-62-1

Literature: Archiv der Pharmazie, , vol. 311, # 8 p. 664 - 671

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Noscapine Structure

Noscapine

CAS#:128-62-1

Literature: Archiv der Pharmazie, , vol. 311, # 8 p. 664 - 671

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Noscapine Structure

Noscapine

CAS#:128-62-1

Literature: Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie, , vol. 184, p. 327,329 Journal of the Chemical Society, , p. 1087,1091

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Noscapine Structure

Noscapine

CAS#:128-62-1

Literature: Archiv der Pharmazie, , vol. 311, # 8 p. 664 - 671

~11%

Noscapine Structure

Noscapine

CAS#:128-62-1

Literature: Acta Chimica Academiae Scientiarum Hungaricae, , vol. 103, # 4 p. 343 - 353

 Articles7

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Peloruside, laulimalide, and noscapine interactions with beta-tubulin.

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 Synonyms

(3S)-3-[(5R)-6-methyl-4-(methyloxy)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-bis(methyloxy)-2-benzofuran-1(3H)-one
MFCD00069316
Coscopin
Noscapal
Vadebex
Vadebe
[3H]-Noscapine
l-α-Narcotine
Narcosine
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-((5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3S)-rel-
Narcotussin
Key-tusscapine
l-a-Narcotine
Longatin
Capval
noscapine
Coscopin (VAN)
Gnoscopine
Methoxyhydrastine
Terbenol
Narcotine (8CI)
Nipaxon
Tusscapine
(S,R)-Noscapine
(-)-α-Narcotine
Narcotine
Opianine
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)-
Terial
Eil
Noscapalin
(3S)-6,7-Dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one
Coscotabs
[S-(R*,S*)]-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3H)-isobenzofuranone
l-a-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinoline
Narcompren
Opian
(-)-noscapine
Opianin
Nectadon
Nicolane
EINECS 204-899-2
Lyobex
(-)-Narcotine
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