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Substance Name: Noscapine [USP:INN:BAN:JAN]
RN: 128-62-1
UNII: 8V32U4AOQU
InChIKey: AKNNEGZIBPJZJG-MSOLQXFVSA-N

Note

  • A naturally occurring opium alkaloid that is a centrally acting antitussive agent.

Molecular Formula

  • C22-H23-N-O7

Molecular Weight

  • 413.4237
 

Classification Codes

  • Antitussive
  • Antitussive Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Natural Product
  • Respiratory System Agents
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Names and Synonyms

Name of Substance

  • Noscapine
  • Noscapine [USP:INN:BAN:JAN]

MeSH Heading

  • Noscapine

Synonyms

  • (-)-3-(2-Methyl-6,7-methylendioxy-8-methoxy-1-isochinolyl)-6,7-dimethoxyphthalid
  • (-)-alpha-Norcotine
  • (-)-Narcotine
  • 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*))-
  • 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*))-
  • 4-27-00-06838 (Beilstein Handbook Reference)
  • 5-(6,7-Dimethoxyphthalidyl)-5,6,7,8-tetrahydro-4-methoxy-8-methyl-1,3-dioxolo(4,5-g)isoquinoline
  • 8-Methoxyhydrastin
  • alpha-Narcotine
  • BRN 0099933
  • Capval
  • CCRIS 9304
  • Coscopin
  • Coscopin (VAN)
  • Coscotabs
  • EINECS 204-899-2
  • Hederix (free base)
  • HSDB 3372
  • Key-tusscapine
  • L-alpha-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinaline
  • L-alpha-Narcotine
  • L-alpha-Noscapine
  • Longactin
  • Longatin
  • Lyobex
  • Methoxyhydrastine
  • Narcompren
  • Narcosine
  • Narcotin
  • Narcotine
  • Narcotussin
  • Narkotin
  • Nectadon
  • Nicolane
  • Nipaxon
  • Noscapalin
  • Noscapin
  • Noscapina
  • Noscapina [INN-Spanish]
  • Noscapine
  • Noscapinum
  • Noscapinum [INN-Latin]
  • Noskapin
  • NSC 5366
  • O-Methylnarcotoline
  • Opian
  • Opianin
  • Opianine
  • Terbenol
  • Tusscapine
  • UNII-8V32U4AOQU
  • Vadebex

Systematic Names

  • 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)-
  • 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*))-
  • Narcotine
  • Noscapine

Registry Numbers

CAS Registry Number

  • 128-62-1

FDA UNII

  • 8V32U4AOQU

Other Registry Numbers

  • 1368-39-4
  • 567-86-2
  • 8055-18-3
  • 8057-19-0

System Generated Number

  • 0000128621

Structure Descriptors

InChI

InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

InChIKey

AKNNEGZIBPJZJG-MSOLQXFVSA-N

Smiles

COc1ccc2[C@H](OC(=O)c2c1OC)[C@@H]3N(C)CCc4cc5OCOc5c(OC)c34

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 73200ug/kg (73.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 323, 1968.
mouse LD50 intraperitoneal 960mg/kg (960mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 24, Pg. 2331, 1982.
mouse LD50 intravenous 83mg/kg (83mg/kg)   Toxicology and Applied Pharmacology. Vol. 3, Pg. 96, 1961.
mouse LD50 oral 853mg/kg (853mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 24, Pg. 2331, 1982.
mouse LD50 subcutaneous 725mg/kg (725mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 338, 1968.
rat LD50 oral 1520mg/kg (1520mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 24, Pg. 2331, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 176 deg C   EXP
log P (octanol-water) 1.970 (none)   EST
Water Solubility 300 mg/L 30 EXP
Atmospheric OH Rate Constant 3.08E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.