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Colchicine
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Name

Colchicine

 EINECS 200-598-5
CAS No. 64-86-8 Density 1.25 g/cm3
PSA 83.09000 LogP 3.26250
Solubility 45 g/L (20 °C) in water Melting Point 150-160 °C (dec.)(lit.)
Formula C22H25NO6 Boiling Point 726 °C at 760 mmHg
Molecular Weight 399.444 Flash Point 392.9 °C
Transport Information UN 1544 6.1/PG 1 Appearance Yellow solid
Safety 13-45 Risk Codes 26/28
Molecular Structure Molecular Structure of 64-86-8 (Colchicine) Hazard Symbols ToxicT, VeryT+
Synonyms

Acetamide,N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-;Colchicine (8CI);(-)-Colchicine;(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide;Colchineos;Colchisol;Colcin;Colsaloid;Condylon;NSC 757;

Article Data 23

Colchicine Synthetic route

108-24-7

acetic anhydride

186374-95-8

(S)-tert-butyl N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate

64-86-8

colchicine

Conditions
ConditionsYield
Stage #1: (S)-tert-butyl N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate With hydrogenchloride In diethyl ether at 20℃; for 1h;
Stage #2: acetic anhydride With dmap; triethylamine In diethyl ether at 25℃; for 10h;		98%

methoxymagnesium bromide

10-demethoxy-10-tosylcolchicine

64-86-8

colchicine

Conditions
ConditionsYield
In tetrahydrofuran for 5h;85%

C22H27NO7

64-86-8

colchicine

Conditions
ConditionsYield
With N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 12h; Inert atmosphere;81%
With N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate In dichloromethane81%
With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at 20℃; for 2h;75%
109-88-6, 16436-83-2, 16436-85-4

magnesium methanolate

10-demethoxy-10-tosylcolchicine

64-86-8

colchicine

Conditions
ConditionsYield
In methanol78%
186581-53-3, 908094-01-9

diazomethane

60-29-7

diethyl ether

67-66-3

chloroform

477-27-0, 1990-46-1

colchiceine

A

64-86-8

colchicine

B

518-12-7

(7S)-isocolchicine

...Expand
186581-53-3, 908094-01-9

diazomethane

477-27-0, 1990-46-1

colchiceine

A

64-86-8

colchicine

B

518-12-7

(7S)-isocolchicine

Conditions
ConditionsYield
With diethyl ether; chloroform
186581-53-3, 908094-01-9

diazomethane

33530-04-0

2,10-didemethylcolchicine

A

64-86-8

colchicine

B

7336-36-9

2-demethylcolchicine

C

518-12-7

(7S)-isocolchicine

D

142713-50-6

2-demethylisocolchicine

Conditions
ConditionsYield
In diethyl ether; chloroform
...Expand
133946-40-4

<1-3H>-3-phenylpropanal

64-86-8

colchicine

Conditions
ConditionsYield
Colchicum byzantinum biosynthesis;
4469-06-1

<3-14C>-cinnamic acid

64-86-8

colchicine

Conditions
ConditionsYield
Colchicum byzantinum biosynthesis;
3476-50-4

deacetylcolchicine

108-24-7

acetic anhydride

64-86-8

colchicine

Conditions
ConditionsYield
With sodium hydrogencarbonate In chloroform; water for 2.5h;
Acetylation;

Colchicine Chemical Properties


IUPAC: N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
Molecular Formula:C22H25NO6
Molecular Weight:399.44
EINECS:200-598-5
Melting Point:150-160 °C (dec.)(lit.)
Solubility: H2O: 10 mg/mL
Form:Powder
Color:White to yellow with a green cast
Water Solubility:45 g/L (20 °C)
Classification Code: 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
Index of Refraction: 1.584 
Molar Refractivity: 106.6 cm3 
Molar Volume: 318.1 cm3
Surface Tension: 50.5 dyne/cm 
Density: 1.25 g/cm3 
Flash Point: 392.9 °C 
Enthalpy of Vaporization: 106.01 kJ/mol 
Boiling Point: 726 °C at 760 mmHg  
Vapour Pressure of Colchicine (CAS NO.64-86-8): 6.21E-21 mmHg at 25 °C

Colchicine Uses

Colchicine(64-86-8) is used as an antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signal.

Colchicine Toxicity Data With Reference

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"

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 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: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

VASCULAR: SHOCK

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 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) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

GASTROINTESTINAL: NAUSEA OR VOMITING		 Archives of Internal Medicine. Vol. 137, Pg. 394, 1977.
man LDLo intravenous 143ug/kg/5D-I (0.143mg/kg) BLOOD: APLASTIC ANEMIA

MUSCULOSKELETAL: OTHER CHANGES		 New England Journal of Medicine. Vol. 309, Pg. 310, 1983.
man LDLo oral 11mg/kg (11mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"		 Canadian Medical Association Journal. Vol. 138, Pg. 335, 1988.
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: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Toxicology and Applied Pharmacology. Vol. 13, Pg. 50, 1968.
rat LDLo intracrebral 1mg/kg (1mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 109, Pg. 386, 1957.
rat LDLo intraperitoneal 1400ug/kg (1.4mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

MUSCULOSKELETAL: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 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) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BLOOD: HEMORRHAGE		 Nouvelle Presse Medicale. Vol. 9, Pg. 1587, 1980.
women LDLo oral 600ug/kg (0.6mg/kg) CARDIAC: OTHER CHANGES

BLOOD: APLASTIC ANEMIA		 American Journal of Emergency Medicine. Vol. 16, Pg. 603, 1998.
women LDLo oral 3mg/kg (3mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES

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

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Journal of Analytical Toxicology. Vol. 4, Pg. 153, 1980.
women TDLo oral 320ug/kg (0.32mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 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) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BLOOD: LEUKOPENIA		 Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 71, 1995.
women TDLo oral 4368ug/kg/26W (4.368mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Neurology. Vol. 41, Pg. 943, 1991.
 

Colchicine Consensus Reports

EPA Extremely Hazardous Substances List. EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Colchicine Safety Profile

A human poison by ingestion and intravenous routes. Poison experimentally by most routes. Human systemic effects: aplastic anemia, blood pressure depression, body temperature decrease, changes in kidney tubules, dyspnea, flaccid paralysis without anesthesia, gastrointestinal effects, kidney damage and hemorrhaging, muscle contraction or spasticity, muscle weakness, nausea or vomiting, respiratory stimulation, and somnolence. An experimental teratogen. Experimental reproductive effects. A severe eye irritant. Human mutation data reported. Inhibits the formation of microtubules and thus impairs cell division. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: VeryT+,ToxicT
Risk Statements: 26/28 
R26/28:Very toxic by inhalation and if swallowed.
Safety Statements: 13-45 
S13:Keep away from food, drink and animal foodstuffs. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 1544 6.1/PG 1
WGK Germany: 3
RTECS: GH0700000
HazardClass: 6.1
PackingGroup: I

Colchicine Specification

  Colchicine (CAS NO.64-86-8), its Synonyms are 7-alpha-H-Colchicine ; 7alphaH-Colchicine ; AI3-31149 ; Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)- ; Benzo(a)heptalen-9(5H)-one, 7-acetamido-6,7-dihydro-1,2,3,10-tetramethoxy- ; 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)- . It is odorless or nearly odorless pale yellow needles or powder that darkens on exposure to light.

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