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Substance Name: Colchicine [USP:JAN]
RN: 64-86-8
UNII: SML2Y3J35T
InChIKey: IAKHMKGGTNLKSZ-INIZCTEOSA-N

Note

  • A major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (PERIODIC DISEASE).

Molecular Formula

  • C22-H25-N-O6

Molecular Weight

  • 399.4405
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Antimitotic Agents
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Gout Suppressants
  • Human Data
  • Mitosis Modulators
  • Mutation Data
  • Reproductive Effect
  • Skin / Eye Irritant
  • Suppressant (gout)
  • Tubulin Modulators

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 10/10000 lb

Names and Synonyms

Name of Substance

  • Colchicine
  • Colchicine [USP:JAN]

MeSH Heading

  • Colchicine

Synonyms

  • 7-alpha-H-Colchicine
  • 7alphaH-Colchicine
  • Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
  • AI3-31149
  • Benzo(a)heptalen-9(5H)-one, 7-acetamido-6,7-dihydro-1,2,3,10-tetramethoxy-
  • CCRIS 691
  • Colchicin
  • Colchicin [German]
  • Colchicina
  • Colchicina [Italian]
  • Colchicine
  • Colchicinum
  • Colchineos
  • Colchisol
  • Colchysat
  • Colcin
  • Colcrys
  • Colsaloid
  • Condylon
  • EC 200-598-5
  • EINECS 200-598-5
  • Goutnil
  • HSDB 3044
  • Kolkicin
  • Mitigare
  • N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide
  • N-Acetyl trimethylcolchicinic acid methylether
  • NSC 757
  • UNII-SML2Y3J35T

Systematic Names

  • Acetamide, N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-
  • Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
  • Colchicine

Superlist Name

  • Colchicine

Mixture Name

  • Colbenemid

Registry Numbers

CAS Registry Number

  • 64-86-8

FDA UNII

  • SML2Y3J35T

Other Registry Numbers

  • 30512-31-3
  • 5843-86-7

System Generated Number

  • 0000064868

Structure Descriptors

InChI

InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1

InChIKey

IAKHMKGGTNLKSZ-INIZCTEOSA-N

Smiles

COC1=CC=C2C(=CC1=O)[C@H](CCc3cc(OC)c(OC)c(OC)c23)NC(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 31600ug/kg (31.6mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LD50 intravenous 250ug/kg (0.25mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING		 Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 261, 1952.
cat LDLo oral 125ug/kg (0.125mg/kg)   "Principles of Insect Chemosterilization," Labrecque, G.C., and C.N. Smith, eds., New York, Appleton-Century-Crofts, 1968Vol. -, Pg. 315, 1968.
cat LDLo subcutaneous 500ug/kg (0.5mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1337, 1935.
child TDLo parenteral 2400ug/kg (2.4mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

GASTROINTESTINAL: NAUSEA OR VOMITING		 Veterinary and Human Toxicology. Vol. 37, Pg. 366, 1995.
dog LDLo oral 125ug/kg (0.125mg/kg)   "Principles of Insect Chemosterilization," Labrecque, G.C., and C.N. Smith, eds., New York, Appleton-Century-Crofts, 1968Vol. -, Pg. 315, 1968.
dog LDLo subcutaneous 571ug/kg (0.571mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1337, 1935.
dog LDLo unreported 5mg/kg (5mg/kg)   Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 27, Pg. 119, 1890.
gerbil LD50 intraperitoneal 90mg/kg (90mg/kg)   Medicina et Pharmacologia Experimentalis. Vol. 17, Pg. 323, 1967.
guinea pig LD50 intraperitoneal 500ug/kg (0.5mg/kg)   Medicina Experimentalis. Vol. 6, Pg. 101, 1962.
guinea pig LDLo oral 12500ug/kg (12.5mg/kg) LIVER: OTHER CHANGES

BLOOD: CHANGES IN SPLEEN

BLOOD: OTHER CHANGES		 Virchows Archiv fuer Pathologische, Anatomie und Physiologie, und fuer Klinische Medizin. Vol. 320, Pg. 93, 1951.
hamster LD50 intraperitoneal 7300ug/kg (7.3mg/kg)   Medicina Experimentalis. Vol. 6, Pg. 101, 1962.
human LDLo intravenous 129ug/kg (0.129mg/kg) VASCULAR: SHOCK

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Human Toxicology. Vol. 2, Pg. 169, 1983.
human LDLo oral 86ug/kg (0.086mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: OTHER CHANGES		 "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 184, 1969.
human TDLo parenteral 710ug/kg (0.71mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Archives of Internal Medicine. Vol. 137, Pg. 394, 1977.
man LDLo intravenous 143ug/kg/5D-I (0.143mg/kg) MUSCULOSKELETAL: OTHER CHANGES

BLOOD: APLASTIC ANEMIA		 New England Journal of Medicine. Vol. 309, Pg. 310, 1983.
man LDLo oral 11mg/kg (11mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Canadian Medical Association Journal. Vol. 138, Pg. 335, 1988.
man TDLo oral 400ug/kg (0.4mg/kg)   Critical Care Medicine. Vol. 7, Pg. 278, 1979.
man TDLo oral 400ug/kg (0.4mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"		 Critical Care Medicine. Vol. 7, Pg. 278, 1979.
man TDLo oral 12514ug/kg/2Y (12.514mg/kg) BEHAVIORAL: MUSCLE WEAKNESS New England Journal of Medicine. Vol. 316, Pg. 1562, 1987.
mouse LD50 intramuscular 1197ug/kg (1.197mg/kg)   Journal of Medicinal Chemistry. Vol. 24, Pg. 257, 1981.
mouse LD50 intraperitoneal 1600ug/kg (1.6mg/kg)   Journal of Medicinal Chemistry. Vol. 28, Pg. 1204, 1985.
mouse LD50 intravenous 1700ug/kg (1.7mg/kg)   Drugs in Japan Vol. 6, Pg. 280, 1982.
mouse LD50 oral 5886ug/kg (5.886mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 1200ug/kg (1.2mg/kg)   Drugs in Japan Vol. 6, Pg. 280, 1982.
pigeon LDLo unreported 30mg/kg (30mg/kg)   Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 27, Pg. 119, 1890.
quail LD50 oral 42mg/kg (42mg/kg)   Journal of Reproduction and Fertility. Vol. 48, Pg. 371, 1976.
rabbit LDLo intravenous 3mg/kg (3mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 67, Pg. 768, 1909.
rabbit LDLo oral 50mg/kg (50mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 67, Pg. 768, 1909.
rabbit LDLo subcutaneous 5mg/kg (5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 67, Pg. 768, 1909.
rat LD50 intravenous 1600ug/kg (1.6mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Toxicology and Applied Pharmacology. Vol. 13, Pg. 50, 1968.
rat LDLo intracrebral 1mg/kg (1mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 109, Pg. 386, 1957.
rat LDLo intraperitoneal 1400ug/kg (1.4mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

MUSCULOSKELETAL: OTHER CHANGES

BEHAVIORAL: MUSCLE WEAKNESS		 Archives of Neurology Vol. 24, Pg. 72, 1971.
rat LDLo parenteral 1000ug/kg (1mg/kg)   Farmaco, Edizione Scientifica. Vol. 15, Pg. 533, 1960.
rat LDLo subcutaneous 4mg/kg (4mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 84, Pg. 257, 1950.
rat LDLo unreported 1mg/kg (1mg/kg)   "Principles of Insect Chemosterilization," Labrecque, G.C., and C.N. Smith, eds., New York, Appleton-Century-Crofts, 1968Vol. -, Pg. 315, 1968.
women LDLo intravenous 360ug/kg/6D (0.36mg/kg) BLOOD: HEMORRHAGE

KIDNEY, URETER, AND BLADDER: OTHER CHANGES 		Nouvelle Presse Medicale. Vol. 9, Pg. 1587, 1980.
women LDLo oral 600ug/kg (0.6mg/kg) BLOOD: APLASTIC ANEMIA

CARDIAC: OTHER CHANGES		 American Journal of Emergency Medicine. Vol. 16, Pg. 603, 1998.
women LDLo oral 3mg/kg (3mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES		 Japanese Journal of Toxicology. Vol. 12, Pg. 337, 1999.
women LDLo oral 8360ug/kg (8.36mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"		 Journal of Analytical Toxicology. Vol. 4, Pg. 153, 1980.
women TDLo oral 320ug/kg (0.32mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)		 Lancet. Vol. 2, Pg. 1271, 1987.
women TDLo oral 510ug/kg (0.51mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: APLASTIC ANEMIA		 Human & Experimental Toxicology. Vol. 16, Pg. 229, 1997.
women TDLo oral 960ug/kg (0.96mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP New England Journal of Medicine. Vol. 322, Pg. 642, 1995.
women TDLo oral 1mg/kg (1mg/kg) BLOOD: LEUKOPENIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP		 Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 71, 1995.
women TDLo oral 4368ug/kg/26W (4.368mg/kg)   Neurology. Vol. 41, Pg. 943, 1991.
women TDLo oral 4368ug/kg/26W (4.368mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: MUSCLE WEAKNESS		 Neurology. Vol. 41, Pg. 943, 1991.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 156 deg C   EXP
pKa Dissociation Constant 1.85 (none)   EXP
log P (octanol-water) 1.3 (none)   EXP
Water Solubility 4.50E+04 mg/L 25 EXP
Vapor Pressure 3.13E-12 mm Hg 25 EST
Henry's Law Constant 1.79E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.32E-10 cm3/molecule-sec 25 EST

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