2-demethylcolchicine

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Names

[ CAS No. ]:
7336-36-9

[ Name ]:
2-demethylcolchicine

[Synonym ]:
O2-Demethylcolchicin
2-O-demethylcolchicine
3-demethylcolchicine

Chemical & Physical Properties

[ Density]:
1.31g/cm3

[ Boiling Point ]:
766.1ºC at 760mmHg

[ Molecular Formula ]:
C21H23NO6

[ Molecular Weight ]:
385.41000

[ Flash Point ]:
417.1ºC

[ Exact Mass ]:
385.15300

[ PSA ]:
94.09000

[ LogP ]:
2.95950

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GH0880000
CHEMICAL NAME :
Colchicine, O(sup 2)-demethyl-
CAS REGISTRY NUMBER :
7336-36-9
LAST UPDATED :
199409
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C21-H23-N-O6
MOLECULAR WEIGHT :
385.45
WISWESSER LINE NOTATION :
L B677 MV&T&J CO1 DO1 EO1 JMV1 NO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
75 ug/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 109,386,1957
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
19 mg/kg
TOXIC EFFECTS :
Behavioral - food intake (animal) Behavioral - muscle weakness Gastrointestinal - hypermotility, diarrhea
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 94,453,1953
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 109,386,1957
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16577 ug/kg
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,257,1981

Synthetic Route

Precursor & DownStream

Precursor

  • Colchicine
  • diazomethane
  • N-[(7S)-2,10-dihydroxy-1,3-dimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide

DownStream

  • 1, 2-Didemethylcolchicine

Related Compounds

  • 2-Demethyl Colchicine
  • 2-DEMETHYLCOLCHICINE-D3
  • 3-Demethyl Colchicine-d3
  • (2S,3S,4S,5R,6S)-6-[[(7S)-7-acetamido-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  • Thiocolchicine analog
  • 1-Demethylcolchicine
  • COLCHICINE, O(sup 1)-DEMETHYL-, ACETATE