Noscapine

Names

[ CAS No. ]:
128-62-1

[ Name ]:
Noscapine

[Synonym ]:
(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

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]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> GPCR/G Protein >> Sigma Receptor

Research Areas >> Cancer

[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.

[Related Small Molecules]

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

[ 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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Determinants of increased opioid-related mortality in the United States and Canada, 1990-2013: a systematic review.

Am. J. Public Health 104(8) , e32-42, (2014)

We review evidence of determinants contributing to increased opioid-related mortality in the United States and Canada between 1990 and 2013. We identified 17 determinants of opioid-related mortality a...

Adlumiceine methyl ester, a new alkaloid from Fumaria vaillantii.

J. Asian Nat. Prod. Res. 16(12) , 1148-52, (2014)

A new alkaloid, adlumiceine methyl ester (1), together with two known alkaloids, parfumine (2) and N-methylhydrastine methyl ester (3), was isolated from aerial parts of Fumaria vaillantii. The struct...

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

Pharm. Res. 29(11) , 2985-93, (2012)

This article reviews the recent findings regarding the binding sites, binding modes and binding affinities of three novel antimitotic drugs peloruside, laulimalide and noscapine with respect to tubuli...