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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Agricultural Chemical
- Antimitotic Agents
- Antirheumatic Agents
- Antiviral (COVID-19)
- 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
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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/s1InChIKey
IAKHMKGGTNLKSZ-INIZCTEOSA-NSmiles
COC1=CC=C2C(=CC1=O)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.