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128-62-1

128-62-1 structure
128-62-1 structure
  • Name: Noscapine
  • Chemical Name: (-)-noscapine
  • CAS Number: 128-62-1
  • Molecular Formula: C22H23NO7
  • Molecular Weight: 413.421
  • Catalog: analytical chemistry Standard Pharmacopoeia Standards and Magazine Standards
  • Create Date: 2018-02-04 08:00:00
  • Modify Date: 2026-07-01 17:01:38
  • 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.
Name (-)-noscapine
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
Coscopin
L-a-Noscapine
Vadebex
Vadebe
NOSCAPINE
l-α-Narcotine
Narcotussin
Key-tusscapine
Longatin
l-alpha-noscapine
Coscopin (VAN)
Terbenol
Nkotin
Ncotussin
(S,R)-NOSCAPINE
Ncosine
Tusscapine
(S,R)-Noscapine
1,3-Dioxolo[4,5-g]isoquinoline, 1(3H)-isobenzofuranone deriv
6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1(3h)-isobenzofuranon
NOSCAPINE (NCOTINE) NATURALLY OCCURRIN G O
Terial
Eil
nsc5366
(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
l-a-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinoline
Opian
Opianin
6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3H)-one
Nectadon
Nicolane
EINECS 204-899-2
MFCD00069316
Noscapal
Noscapin
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]
[3H]-Noscapine
Narcosine
Hederix (free base)
l-a-Narcotine
Capval
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
a-Ncotine
alpha-Ncotine
noscapine
O-Methylncotoline
Gnoscopine
Methoxyhydrastine
(-)-a-Ncotine
l-a-Ncotine
Key-Tusscapine
(S)-6,7-DIMETHOXY-3-((R)-4-METHOXY-6-METHYL-5,6,7,8-TETRAHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-5-YL)-3H-ISOBENZOFURAN-1-ONE
Narcotine (8CI)
5-g]isoquinolin-5-yl)-,[s-(theta,s)]-3-dioxolo[4
NCOTINE
(3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone
Ncompren
Ncotin
Nipaxon
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)- (9CI)
(-)-α-Narcotine
Phthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)
Narcotine
Opianine
L-ALPHA-NCOTINE
Noscapalin
tusseapine
Gnoscopine [dl-form]
[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
[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-alpha-2-methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1
Narcompren
1-alpha-Ncotine
2,3,4-tetrahydroisoquinaline
dl-Ncotine [dl-form]
5-g)isoquinolin-5-yl)-,(s-(r*,s*))-3-dioxolo(4
Lyobex
(-)-Narcotine
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.
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℃

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)
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)
488721-01-3 structure

488721-01-3

~14%

1214255-25-0 structure

1214255-25-0

128-62-1 structure

128-62-1

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 8 p. 2983 - 2987
68353-58-2 structure

68353-58-2

~%

128-62-1 structure

128-62-1

Literature: Archiv der Pharmazie, , vol. 311, # 8 p. 664 - 671
3860-46-6 structure

3860-46-6

~%

128-62-1 structure

128-62-1

Literature: Archiv der Pharmazie, , vol. 311, # 8 p. 664 - 671
186581-53-3 structure

186581-53-3

~%

128-62-1 structure

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
186581-53-3 structure

186581-53-3

68353-55-9 structure

68353-55-9

~%

128-62-1 structure

128-62-1

Literature: Archiv der Pharmazie, , vol. 311, # 8 p. 664 - 671
70253-41-7 structure

70253-41-7

~11%

35933-62-1 structure

35933-62-1

128-62-1 structure

128-62-1

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