Noscapine

HCID 275196
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
128-62-1
Standard SMILES
COc1ccc2c(c1OC)C(=O)O[C@@H]2[C@H]1c2c(cc3c(c2OC)OCO3)CCN1C
InChIKey
AKNNEGZIBPJZJG-MSOLQXFVSA-N
Molecular formula
C22H23NO7
Average molar mass
413.4 g/mol
Monoisotopic mass
413.14745207

Names & identifiers

Preferred name
Noscapine
IUPAC
(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
English name
Narcotine
Molecular formula
C22H23NO7
Molecular weight
413.42

Names & synonyms

noscapine128-62-1NARCOTINETusscapineMethoxyhydrastineTerbenolCoscopinNarcomprenNarcosineVadebexNoscapalinLongatin
Show more names
OpianVadebeCapvalEcasilTerialOpianinnsc5366
Opianine(-)-NarcotineNarcotinNarcotussinNectadonNicolaneNoscapinLyobex

Database identifiers

CAS
128-62-1、6035-40-1
PubChem CID
275196
ChEMBL
CHEMBL364713
ChEBI
CHEBI:73237
UNII
8V32U4AOQU、A4C6WE7BZN
EC Number
204-899-2
Nikkaji
J9.283E

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
75.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
8
Rotatable bonds
4
Heavy atoms
30

Experimental & physicochemical properties

pHNEUTRAL TO LITMUS
OdorODORLESS
TasteVERY BITTER TASTE
Density1.395
Color/Form · 2 items

ORTHORHOMBIC BISPHENOIDAL PRISMS

FINE, WHITE, OR PRACTICALLY WHITE, CRYSTALLINE POWDER

Solubility · 6 items

PKA 6.24; FREELY SOL IN ETHANOL; INSOL IN DIETHYL ETHER /HYDROCHLORIDE/

FINE, WHITE, OR PRACTICALLY WHITE, CRYSTALLINE POWDER; ODORLESS OR HAS SLIGHT ODOR OF ETHANOL; FREELY SOL IN CHLOROFORM & METHANOL; SOL IN ALCOHOL; SPARINGLY SOL IN ACETONE; PRACTICALLY INSOL IN ETHER; SOLN IN WATER IS DEXTROROTATORY; PH OF SOLN (1 IN 20) BETWEEN 2.5 & 3.5 /HYDROCHLORIDE/

HEMIHYDRATE TO TETRAHYDRATE, CRYSTALS; VERY SOL IN WATER /HYDROCHLORIDE/

CRYSTALS; FREELY SOL IN WATER; SOL IN METHANOL, ETHANOL; SLIGHTLY SOL IN ETHYL ACETATE; PRACTICALLY INSOL IN ETHER /CAMPHORSULFONATE/

PRACTICALLY INSOL IN VEGETABLE OILS; SLIGHTLY SOL IN NH4OH, HOT SOLN OF KOH & NAOH

SLIGHTLY SOL IN ALCOHOL & ETHER

Physicochemical properties

Melting point
174 · 174-176 °C(lit.)
alpha
-200 · -200 º (c=1 in chloroform)
Boiling point
532.6 °C · 532.6°C (rough estimate)
Density
1.395 · 1.395
refractive index
1.5614 · 1.5614 (estimate)
storage temp.
-20 °C · -20°C Freezer, Under Inert Atmosphere

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 140 reports by companies from 4 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Chemical: 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*)]-

Status: Active Update: 29-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19776

Other Safety Information · 1 item

IMAP assessments - 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*)]-: Environment tier I assessment；IMAP assessments - 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*)]-: Human health tier I assessment

Hazard Classes and Categories · 2 items

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

Toxicology

Natural Pollution Sources · 2 items

...NATURALLY OCCURRING OPIUM ALKALOID OF BENZYLISOQUINOLINE GROUP...

...NATURALLY OCCURRING (LEVO-FORM) OF ALKALOID NARCOTINE. ... ISOLATED FROM OPIUM IN WHICH IT IS PRESENT IN AMT RANGING FROM 3-10%.

Human Toxicity ExcerptsADVERSE REACTIONS OCCUR INFREQUENTLY & INCL DROWSINESS, HEADACHE, NAUSEA, NONSEASONAL ALLERGIC (VASOMOTOR) RHINITIS, & CONJUNCTIVITIS.
Non-Human Toxicity ExcerptsIN DOGS, DRUG IS POTENT RELEASER OF HISTAMINE, & LARGE DOSES CAUSE BRONCHOCONSTRICTION & TRANSIENT HYPOTENSION. TOXIC DOSES PRODUCE CONVULSIONS IN ANIMALS.

Regulatory information

Regulatory Information · 2 items

Chemical: 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*)]-

Status: Active Update: 29-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19776

Safety data

wgk
3
rtecs
RD2625000
ridadr
1544
hs_code
29329990
Toxicity
cyt-ham:lng 100 mg/L ATSUDG (4),41,80
risk_code
22

Chemistry & industry

Pharmacology

ATC Code · 2 items

R - Respiratory system；R05 - Cough and cold preparations；R05D - Cough suppressants, excl. combinations with expectorants；R05DA - Opium alkaloids and derivatives；R05DA07 - Noscapine

QR - Respiratory system；QR05 - Cough and cold preparations；QR05D - Cough suppressants, excl. combinations with expectorants；QR05DA - Opium alkaloids and derivatives；QR05DA07 - Noscapine

Mechanism of Action · 2 items

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.

...EXCEPT FOR ITS ANTITUSSIVE EFFECT, IT HAS NO SIGNIFICANT ACTIONS ON CNS IN DOSES WITHIN THERAPEUTIC RANGE.

Metabolism/Metabolites · 1 item

MECONIN WAS THE MAJOR URINARY METABOLITE OF RATS, RABBITS, & HUMANS WHO HAD RECEIVED 120, 150 MG/KG & 10 MG, RESPECTIVELY, ORALLY. IT ACCOUNTED FOR APPROX 3, 8, & 2% OF DOSE RESPECTIVELY, AFTER 24 HR. O-DEMETHYLATED METABOLITES WERE ALSO FOUND.

MeSH Pharmacological ClassificationAgents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.
Absorption, Distribution and ExcretionITS ANTITUSSIVE POTENCY & ONSET & DURATION OF ACTION ARE APPROX EQUAL, MG FOR MG, TO THOSE OF CODEINE.
Cellular LocationsCytoplasm；Extracellular

Uses & manufacturing

Uses · 2 items

MEDICATION

Use (kg; approx.) in Germany (2009): >1000；Consumption (g per capita; approx.) in Germany (2009): 0.0122；Excretion rate: 1；Calculated removal (%): 46.5

Methods of ManufacturingMAILLARD, US PATENT 3,108,106 (1963 TO JACQUES LOGEAIS).
Formulations/PreparationsTUSSCAPINE (FISONS). ORAL: LIQUID 15 MG/5 ML
Use ClassificationPharmaceuticals
General Manufacturing InformationOPIUM ALKALOID, ISOLATED FROM PLANT PAPAVER SOMNIFERUM L PAPAVERACEAE. FIRST ISOLATION: ROBIQUET, ANN CHIM PHYS (2) 5, 275 (1817). EXTRACTABLE FROM WATER INSOLUBLE RESIDUE REMAINING FROM PROCESSING OF OPIUM FOR MANUFACTURE OF MORPHINE.
Applications · 3 items

DescriptionA major constituent of opium (Papaver sornni!erurn), this phthalideisolquinoline base was probably first discovered by Derosne, but initially characterized by Robiquet who gave it the formula C23H3S0 7N, changed to that now accepted by Matthiesen and Foster. It crystallizes in colourless needles from EtOH and has [α]D - 198° (c 1.0, CHC13); - 146° (c 2.0, toluene); - 147° (c 1.59, C6H6) and + 50° (1 % HCl). The alkaloid is a weak, monoacidic, tertiary base, forming unstable salts with acids which are dissociated with H20. The hydrochloride crystallizes with varying amounts of H20, is very soluble in water, readily decomposing into basic salts on standing. The platinichloride is amorphous; the oxalate has m.p. 174°C;[α]20D + 39.5° (H20); the phthalate, m.p. 160°C; [α]22D + 115° (CHC13); sesquisulphate, colourless crystals of the hexahydrate and the picrate, m.p. 1 74-S°C. The (+)-bromocamphorsulphonate has m.p. 110- 120°C; [α]D + 100.7° (CHC13) and the corresponding (-)-bromocamphorsul_x0002_phonate, m.p. l80.SoC; [α]D + 29° (CHC13). The alkaloid yields an N-oxide which is a hygroscopic solid; [α]D + 135° (CHC13) furnishing a crystalline hydrochloride, m.p. 193°C; platinichloride, m.p. 175°C and a picrate, m.p. 130°C.The base is unstable to heat and when heated in a sealed tube yields a mixture of dimethylnornarcotine, methylnornarcotine and nornarcotine. On heating with H20 and 150°C, or on boiling with dilute acids, it is hydrolyzed to opianic acid and hydrocotarnine. Similar degradations are brought about by acid oxidation orreduction, e.g. Zn and dilute HCl gives hydrocotarnine and meconin while dilute HN03 yields cotarnine and opianic acid. Pharmacologically, narcotine resembles thebaine (q.v.) in its action, being a reflex stimulant rather than a narcotic.

Usesantiacne, antiproliferative agent

UsesAntitussive.

Upstream & downstream products

Suppliers65 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from p ants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.

Related reactions

7 records
New reaction record

Compound notes

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