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Substance Name: Sinomenine
RN: 115-53-7
UNII: 63LT81K70N
InChIKey: INYYVPJSBIVGPH-QHRIQVFBSA-N

Note

  • Isolated from root of Sinomenium acutum; antirheumatic, antineuralgic.

Classification Codes

  • Antirheumatic Agents
  • Drug / Therapeutic Agent

Molecular Formula

  • C19-H23-N-O4

Molecular Weight

  • 329.394
 
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Names and Synonyms

Name of Substance

  • Sinomenine

Synonyms

  • 5-21-13-00516 (Beilstein Handbook Reference)
  • 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-morphinan-6-one
  • BRN 0095280
  • CCRIS 1550
  • Coculine
  • Cucoline
  • EINECS 204-094-6
  • Kukoline
  • Sabianine A
  • Sinomenine
  • UNII-63LT81K70N

Systematic Names

  • (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
  • 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-
  • Sinomenine

Registry Numbers

CAS Registry Number

  • 115-53-7

FDA UNII

  • 63LT81K70N

Related Registry Number

  • 6080-33-7 (hydrochloride salt)

System Generated Number

  • 0000115537

Structure Descriptors

InChI

1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1

InChIKey

INYYVPJSBIVGPH-QHRIQVFBSA-N

Smiles

O=C1C(=C[C@H]2[C@@]3(c4c(c(ccc4C[C@@H]2[N@@](CC3)C)OC)O)C1)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 285mg/kg (285mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 8, Pg. 177, 1960.
mouse LD50 oral 580mg/kg (580mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 10, Pg. 673, 1963.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 162 deg C   EXP
log P (octanol-water) 1.050 (none)   EST
Atmospheric OH Rate Constant 3.01E-10 cm3/molecule-sec 25 EST

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