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Substance Name: Demecolcine [INN:BAN:DCF]
RN: 477-30-5
UNII: Z01IVE25KI
InChIKey: NNJPGOLRFBJNIW-HNNXBMFYSA-N

Note

  • An alkaloid isolated from Colchicum autumnale L. and used as an antineoplastic.

Molecular Formula

  • C21-H25-N-O5

Molecular Weight

  • 371.4305
 

Classification Codes

  • Antimitotic Agents
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
  • Human Data
  • Mitosis Modulators
  • Mutation Data
  • Reproductive Effect
  • Tubulin Modulators
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Names and Synonyms

Name of Substance

  • Demecolcine
  • Demecolcine [INN:BAN:DCF]

MeSH Heading

  • Demecolcine

Synonyms

  • (-)-Colchamine
  • (-)-Demecolcine
  • 4-14-00-00940 (Beilstein Handbook Reference)
  • 6,7-Dihydro-1,2,3,10-tetramethoxy-7-(methylamino)-benzo(alpha)heptalen-9(5H)-one
  • Alkaloid H 3, from colchicum antumnale
  • BRN 2822892
  • C-12669
  • CCRIS 2764
  • Ciba 12669A
  • Colcemid
  • Colchamine
  • Colchicine, 7-deacetamido-7-(methylamino)-
  • Colchicine, N-deacetyl-N-methyl-
  • Deacetyl-N-methylcolchicine
  • Deacetylmethylcolchicine
  • Demecolcin
  • Demecolcina
  • Demecolcina [INN-Spanish]
  • Demecolcine
  • Demecolcinum
  • Demecolcinum [INN-Latin]
  • Desacetylmethylcolchicine
  • Desmecolcine
  • EINECS 207-514-6
  • Kolchamin
  • Kolchicin
  • Kolchicin [Czech]
  • Kolkamin
  • Methylcolchicine
  • N-Deacetyl-N-methylcolchicine
  • N-Desacetyl-N-methylcolchicine
  • N-Desacetylmethylcolchicine
  • N-Methyl-N-deacetylcolchicine
  • N-Methyl-N-desacetylcolchicine
  • NSC 3096
  • Omain
  • Omaine
  • Reichstein's F
  • Santavy's substance F
  • Substance F
  • UNII-Z01IVE25KI
  • X 153

Systematic Names

  • Benzo(a)heptalen-9(5H)-one, 6,7-dihydro-1,2,3,10-tetramethoxy-7-(methylamino)-, (S)-
  • Colchicine, N-deacetyl-N-methyl-
  • Deacetyl-N-methylcolchicine
  • Demecolcin
  • Demecolcine

Registry Numbers

CAS Registry Number

  • 477-30-5

FDA UNII

  • Z01IVE25KI

System Generated Number

  • 0000477305

Structure Descriptors

InChI

1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/t15-/m0/s1

InChIKey

NNJPGOLRFBJNIW-HNNXBMFYSA-N

Smiles

CN[C@H]1CCc2cc(OC)c(OC)c(OC)c2C3=CC=C(OC)C(=O)C=C13

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 200ug/kg (0.2mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 184, 1969.
mouse LD50 intramuscular 87mg/kg (87mg/kg)   Journal of Medicinal Chemistry. Vol. 24, Pg. 257, 1981.
mouse LD50 intraperitoneal 35mg/kg (35mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 230, Pg. 559, 1957.
mouse LD50 intravenous 56mg/kg (56mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Pharmacology and Toxicology. English translation of FATOAO. Vol. 20, Pg. 284, 1957.
mouse LD50 oral 25530ug/kg (25.53mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD50 intravenous 1700ug/kg (1.7mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
rat LD50 parenteral 1700ug/kg (1.7mg/kg)   Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 1.37 (none)   EXP
Water Solubility 3160 mg/L 25 EST
Vapor Pressure 1.48E-09 mm Hg 25 EST
Henry's Law Constant 1.21E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.03E-10 cm3/molecule-sec 25 EST

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