Noscapine (HCID 275196)

Namen und Bezeichner

Bevorzugter 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
Lokaler Name: Noscapin
Englischer Name: Narcotine
Summenformel: C22H23NO7
Molmasse: 413.42

Namen und Synonyme

noscapine128-62-1NARCOTINETusscapineMethoxyhydrastineTerbenolCoscopinNarcomprenNarcosineVadebexNoscapalinLongatin

Weitere Namen anzeigen

OpianVadebeCapvalEcasilTerialOpianinnsc5366

Opianine(-)-NarcotineNarcotinNarcotussinNectadonNicolaneNoscapinLyobex

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,7
Polarare Oberfläche (TPSA): 75,7 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 8
Frei drehbare Bindungen: 4
Schwere Atome: 30
Formalladung: 0
Komplexität: 647

Experimentelle und physikochemische Eigenschaften

pHNEUTRAL TO LITMUS

OdorODORLESS

TasteVERY BITTER TASTE

Density1.395

Color/Form · 2 Einträge

ORTHORHOMBIC BISPHENOIDAL PRISMS

FINE, WHITE, OR PRACTICALLY WHITE, CRYSTALLINE POWDER

Solubility · 6 Einträge

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

Physikochemische Eigenschaften

Schmelzpunkt: 174 · 174-176 °C(lit.)
Siedepunkt: 532.6 °C · 532.6°C (rough estimate)
Dichte: 1.395 · 1.395
Brechungsindex: 1.5614 · 1.5614 (estimate)
storage temp.: -20 °C · -20°C Freezer, Under Inert Atmosphere
Löslichkeit: Practically insoluble in water, soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in strong acids; on dilution of the solution with water, the base may be precipitated.
pka: 7.8 · 7.8(at 25℃)
Aggregatzustand: Solid
Farbe: Orthorhombic prisms or stout needles from alc
Wasserlöslichkeit: 302.9 mg/L · 302.9mg/L(25 ºC)
Merck: 13 · 13,6752
NIST chemische Informationen: Narcotine alkaloid(128-62-1)
EPA chemische Informationen: 1 · 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)- (128-62-1)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

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 Eintrag

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 Einträge

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

Toxikologische Informationen

Natural Pollution Sources · 2 Einträge

...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.

Regulatorische Informationen

Regulatory Information · 2 Einträge

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

Sicherheitsdaten

wgk: 3
ridadr: 1544
hs_code: 29329990
RTECS-Nr.: RD2625000
risk_code: 22
Toxizität: cyt-ham:lng 100 mg/L ATSUDG (4),41,80
hazard_code: Xn
safety_code: 24/25
hazard_class: 6.1(b)
packing_group: III
Giftige Stoffe Daten: 128-62-1(Hazardous Substances Data)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

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 Einträge

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 Eintrag

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

Verwendung und Herstellung

Uses · 2 Einträge

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.

Anwendungen · 1 Eintrag

BeschreibungA 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

(-)-β-Narcotine 7-O-DeMethyl α-Narcotine

Nachgelagerte Produkte

(3S)-3-[(5R)-9-amino-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one Cotarnin [S-(R*,S*)]-3,4-Dimethoxy-α1-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isochinolin-5-yl)-o-xylol-α,α'-diol

Anbieter50 Anbieter

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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]

Ergänzende Hinweise · 1 Eintrag

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.