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Colchicine(CAS No. 64-86-8)

Colchicine C22H25NO6 (cas 64-86-8) Molecular Structure

64-86-8 Structure

Identification and Related Records

【CAS Registry number】
Acetamide,N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
Colchicine (8CI)
Benzo[a]heptalene, acetamide deriv.
NSC 757
【Molecular Formula】
C22H25NO6 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

yellow powder
1.32 g/cm3
【Melting Point】
【Boiling Point】
【Refractive Index】
【Flash Point】
-250 o (C=1, ALCOHOL)
45 g/L (20℃)
white to yellow with a green cast
Stable. Light sensitive. Incompatible with strong oxidizing agents.
【Storage temp】
Poison room
【Spectral properties】
Specific optical rotation: -429 at 17 deg C/D (water, 1.72%); -121 deg at 17 deg c/d (concentration by volume = 0.9 g in 100 ml chloroform); max absorption (95% ethanol): 350.5 nm (log epsilon = 4.22), 243 nm (log epsilon = 4.47)
IR: 17152 (Sadtler Research Laboratories Prism Collection)
UV: 5410 (Sadtler Research Laboratories Spectral Collection)
MASS: 35758 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
【Computed Properties】
Molecular Weight:399.437 [g/mol]
Molecular Formula:C22H25NO6
H-Bond Donor:1
H-Bond Acceptor:6
Rotatable Bond Count:5
Tautomer Count:2
Exact Mass:399.168188
MonoIsotopic Mass:399.168188
Topological Polar Surface Area:83.1
Heavy Atom Count:29
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:6
Feature 3D Donor Count:1
Feature 3D Ring Count:3
Effective Rotor Count:6.6
Conformer Sampling RMSD:0.8
CID Conformer Count:21

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

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:?T+,T
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

【PackingGroup 】
Light Sensitive
【Skin, Eye, and Respiratory Irritations】
Eye, skin, gastrointestinal and/or respiratory tract irritation.
【Cleanup Methods】
Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labelled container for disposal. Wash spill site.
Do not touch or walk through the spilled agent if at all possible. However, if you must, personnel should wear the appropriate personal protective equipment (PPE) during environmental decontamination. ... Keep combustibles (e.g., wood, paper, and oil) away from the spilled agent. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact the spilled agent. Do not direct water at the spill or the source of the leak. Stop the leak if it is possible to do so without risk to personnel, and turn leaking containers so that gas rather than liquid escapes. Prevent entry into waterways, sewers, basements, or confined areas. Isolate the area until gas has dispersed. Ventilate the area.
UN 1544
【Fire Fighting Procedures】
If a tank, rail car, or tank truck is involved in a fire, isolate it for 0.5 miles (800 m) in all directions; also consider initial evacuation for 0.5 miles (800 m) in all directions.
For large fires, use water spray, fog, or regular foam. Move containers from the fire area if it is possible to do so without risk to personnel. Dike fire control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. For fire involving tanks or car/trailer loads, fight the fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after the fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tanks. Always stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from the area and let the fire burn. Run-off from fire control or dilution water may be corrosive and/or toxic, and it may cause pollution. If the situation allows, control and properly dispose of run-off (effluent).
For fire involving tanks or car/trailer loads, fight the fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after the fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tanks. Always stay away from tanks engulfed in fire.
Run-off from fire control or dilution water may be corrosive and/or toxic, and it may cause pollution. If the situation allows, control and properly dispose of run-off (effluent).
For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from the area and let the fire burn.
/Colchicine/ is assumed to be combustible. As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.
【Fire Potential】
Grades: technical; United States Pharmacopeia.
Oral: Tablets: 0.6 mg (Colchicine Tablets). NOTE: Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name.
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl colchicine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Eye, skin, gastrointestinal and/or respiratory tract irritation.

? 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.

【Octanol/Water Partition Coefficient】
log Kow = 1.03

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

【Disposal Methods】
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

The seeds of the meadow saffron (Colchicum autumnale L.) are extracted with boiling alcohol to obtain colchicine. Because of its solubility, it can be separated from accompanying substances: the extract is evaporated and the residue mixed with water. The undissolved resins and fats are filtered off and the filtrate extracted with chloroform. After evaporation of the chloroform solution the procedure is repeated with the residue. When the purity is sufficient, the colchicine crystallizes from the concentrated chloroform solutions as a chloroform complex.
Extraction from the plant Colchicum autumnale with ethanol, followed by water treatment, filtration, extraction with petroleum ether, extraction with chloroform, concentration of the residue, and distillation
By extracting ... seed with alc. After distilling off alc, syrupy residue is diluted with water to precipitate fats and resins and filtered. Filtrate is digested with some lead carbonate, refiltered, evaporated to small vol and colchicine extracted with chloroform.
From Colchicum autumnale by extraction and subsequent crystallization. Has been synthesized.
Consumption Patterns

Essentially 100% as a medicinal (1976)

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

Biomedical Effects and Toxicity

【Biological Activity】
Plant-derived alkaloid that binds to tubulin and depolymerizes microtubules.
【Pharmacological Action】
- Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout.
- Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
【Therapeutic Uses】
Gout Suppressants
Colchicine also is used in the prophylactic treatment of recurrent gouty arthritis. Colchicine has no effect on plasma concentrations or urinary excretion of uric acid; therefore, concomitant administration of allopurinol or a uricosuric agent (e.g., probenecid, sulfinpyrazone) is necessary to decrease serum urate concentrations. Prophylactic doses of colchicine should be administered before the initiation of allopurinol or uricosuric therapy because sudden changes in serum urate concentrations may precipitate acute gout attacks. After the serum urate concentration has been reduced to the desired level and acute gout attacks have not occurred for 3-6 months (some clinicians suggest 1-12 months), colchicine may be discontinued and the patient may be treated with urate lowering agents alone. Colchicine is frequently used in combination with probenecid to facilitate prophylactic therapy in patients with chronic gouty arthritis. The usefulness of the commercially available fixed-dosage preparation is limited, however, because the colchicine present exceeds the amount required by most patients. /Use Included in US product label/
Colchicine is used to relieve attacks of acute gouty arthritis. Nonsteroidal anti-inflammatory agents (NSAIAs) (e.g., indomethacin, ibuprofen, naproxen, sulindac, piroxicam, ketoprofen) are as effective as, and better tolerated than, usual dosages of colchicine for short-term use in relieving acute attacks of gouty arthritis. Corticosteroids also are used to relieve acute attacks of gouty arthritis. Colchicine is considered a second-line agent; colchicine may be used for the treatment of acute gouty arthritis in patients who have not responded to or who cannot tolerate recommended therapies (i.e., NSAIAs, corticosteroids). /Use Included in US product label/
96 patients aged 15 yr or more with complete or incomplete Behcet's disease, whose visual acuity was 20/40 or less, and who had experienced at least 2 episodes of ocular attack during the 16 wk before the study were selected. 47 patients received cyclosporin (10 mg/kg) and 49 colchicine (1 mg/kg) daily for 16 wk. The frequency of ocular attack was reduced more in the cyclosporin group than in the colchicine group (p < 0.001). The severity of ocular attacks was also less severe after cyclosporin than after colchicine (p < 0.001). Colchicine alleviated oral aphthous ulcer in 10 patients (20%). Dermal lesions were alleviated in 15% of the colchicine group. Clinical symptoms were improved in 33% for the colchicine group, and 10 cases were aggravated. OKT4/OKT8 ratios were 1.44 in the colchicine group before the study and 1.46 after treatment. Frequently observed side effects of colchicine were hirsutism (2 patients) and renal dysfunction (2 patients). Treatment was stopped because of hepatic dysfunction in 2 colchicine cases. [Masuda K et al; Lancet 1 (8647): 1093-6 (1989)]
【Biomedical Effects and Toxicity】
The absorption of colchicine is rapid but variable. Peak plasma concentrations occur 0.5 to 2 hours after dosing. In plasma, 50% of colchicine is protein-bound. There is significant enterohepatic circulation. The exact metabolism of colchicine is unknown but seems to involve deacetylation by the liver. Only 10% to 20% is excreted in the urine, although this increases in patients with liver disease. The kidney, liver, and spleen also contain high concentrations of colchicine, but it apparently is largely excluded from heart, skeletal muscle, and brain. The plasma half-life of colchicine is approximately 9 hours, but it can be detected in leukocytes and in the urine for at least 9 days after a single intravenous dose.
... Two cases involving suicide by the ingestion of medications marketed in France /is reported/. In case 1, only heart blood was taken after body external examination. In case 2 an autopsy was performed and heart blood, urine, gastric contents and bile were taken for toxicological analysis. Colchicine was assayed in biological specimens by an HPLC-DAD method, after extraction by dichloromethane at pH 8, adding prazepam as internal standard (IS). Analyses were performed on a Symetry C-8 column. Mobile phase was a gradient of acetonitrile/pH 3.8 phosphate buffer. Colchicine is eluted at 13.1 min and the method is linear for blood, urine and bile over the range 4-1000 ng/mL. LOQ is 4 ng/mL. The concentrations of colchicine detected are: case 1: heart blood 13 ng/mL; case 2: heart blood 66 ng/mL, urine 500 ng/mL, gastric content 12 ng/mL, bile 5632 ng/mL. Our findings are in the range of lethal concentrations previously described, but there is no correlation with the amount of ingested drug. Even after massive overdose, it could be impossible to detect colchicine in blood, and as there is a widespread enterohepatic recirculation before excretion in bile and feces, bile is the target sample to analyse. We conclude in both cases that the cause of death was suicide with colchicine. It appears very important to perform an autopsy in order to obtain bile, urine, heart blood and femoral blood. [Deveaux M et al; Forensic Sci Int 143 (2-3): 219-22 (2004). Available from, as of July 21, 2009:] PubMed Abstract
After oral administration plasma concentrations reach a peak within 0.5 to 2 hours and afterwards decrease rapidly within 2 hours. The plasma half-life is 60 minutes. Colchicine may remain in tissues for as long as 10 days.
Information was available on urinary excretion in 5 cases. Concentrations in urine are 10 to 80 fold higher than those in plasma. Four to 25 per cent of the dose ingested was excreted in urine over three to ten days. Excretion was specially high during the first 24 hours following ingestion. Colchicine is eliminated in urine up to the tenth day.
Colchicine is excreted unchanged (14% to 40%) or as metabolites (4% to 14%) within 48 hours.
Following oral administration, colchicine is absorbed from the GI tract and is partially metabolized in the liver. The drug and its metabolites re-enter the intestinal tract via biliary secretions and the unchanged drug may be reabsorbed from the intestine. Plasma concentrations of colchicine and its metabolites decline at 1-2 hours after ingestion of the drug and then increase, probably as a result of reabsorption of unchanged drug. Recycling of the drug probably accounts for the extensive intestinal manifestations which occur in colchicine poisoning.
Following IV administration of a single therapeutic dose (as of August 2008, IV preparations are no longer commercially available in the US), colchicine is rapidly removed from the plasma; plasma half-life is about 20 minutes. The drug has a half-life of about 60 hours in leukocytes. Colchicine is partly deacetylated in the liver and is also slowly metabolized in other tissues. Colchicine and its metabolites are excreted primarily in feces and lesser amounts are excreted in urine. In one study, patients with severe renal disease eliminated little or no colchicine or its metabolites in the urine resulting in a longer plasma half-life.

To clarify whether colchicine is excreted in breast milk, and to compare its concentrations in the serum and breast milk of lactating women who have familial Mediterranean fever. Using a specific radioimmunoassay, we determined colchicine concentrations in the serum and breast milk of 4 patients at various time points, following oral administration of the drug. The study evaluated 4 patients with familial Mediterranean fever who had been taking colchicine on a long-term basis. Colchicine was found to be excreted in breast milk. Its levels ranged between 1.9 and 8.6 ng/ml, which were similar to those found in the serum (parallel concentration time curves). However, there appeared to be a considerable variation in colchicine milk concentration among the different patients, which might be related to individual breast milk composition and, possibly, to other nutritional or metabolic factors. The extensive peripheral tissue binding and relatively low concentration of colchicine in breast milk suggests that the amount ingested by the infant is small. Furthermore, based on our clinical experience, nursing appears to be safe for lactating women with familial Mediterranean fever who continue to take colchicine. [Ben-Chetrit E et al; Arthritis Rheum 39 (7): 1213-7 (1996). Available from, as of September 28, 2009:] PubMed Abstract
Free and total plasma, granulocyte and mononuclear cell colchicine concentrations were measured by radioimmunoassay in 30 patients with familial Mediterranean fever treated with colchicine 0.5 to 2 mg day-1. Colchicine concentrations showed a large intersubject variability in plasma (0.13-1.75 ng ml-1), granulocytes (4 to 64 ng/10(9) cells), and mononuclear cells (11.4 to 57.6 ng/10(9) cells). Whereas unbound and total plasma colchicine concentrations were well correlated, no correlation was found between total or free plasma and granulocyte or mononuclear cell colchicine concentrations and dose of administered colchicine. In contrast, total or free plasma and granulocyte or mononuclear cell colchicine concentrations were correlated using a hyperbolic function indicating saturable colchicine distribution in both leukocyte populations. [Chappey O et al; Br J Clin Pharmacol 38 (1): 87-9 (1994). Available from, as of September 28, 2009:] PubMed Abstract
After reabsorption, colchicine is rapidly removed from the plasma and distributed into various tissues. Colchicine is concentrated in leukocytes. The drug and its metabolites are also distributed into other tissues including kidneys, liver, spleen, and intestinal tract but appear to be absent in heart, skeletal muscle, and brain. Colchicine is distributed into milk. In a limited number of nursing women receiving long-term colchicine therapy at dosages of 1-1.5 mg daily, peak concentrations of the drug in milk were similar to serum concentrations and ranged from 1.9-8.6 ng/mL. Higher concentrations of the drug in milk (31, 24-27, or 10 ng/mL at 2, 4, or 7 hours, respectively, after a dose) have been reported in the absence of concurrent serum concentration data in a nursing woman receiving colchicine 1 mg daily.
The pharmacokinetics of colchicine were studied in six healthy male and four elderly female volunteers after iv and oral administration. Plasma samples were collected over 72 hr and assayed for colchicine by a specific and sensitive radioimmunoassay. Plasma concentration-time curves were fitted using a three-compartmental model after iv administration of 0.5 mg (healthy volunteers) and 1 mg (elderly group) colchicine. The first distribution half-life was short: 9.2 min in healthy volunteers and 3.0 min in the elderly group; the second distribution half-life was of the same order for both groups, 1.2 hr. Plasma elimination half-lives were also in the same range: 30 hr for healthy volunteers versus 34 h for the elderly subjects. Mean residence time was also in the same range in the two groups: 27 hr in healthy volunteers and 21 h for elderly subjects. The volume of distribution (Vz) was 6.7 for the healthy group and 6.3 for the elderly group, while Vss was smaller: 4.2 for healthy volunteers and 2.9 for elderly subjects. Total body clearance was 10.5 l.h-1 for healthy and 5.5 l.h-1 for elderly subjects. After oral administration of 1 mg, lag-time was 14 min in healthy volunteers and 11 min in elderly subjects. Maximal plasma concentration was 5.5 at 62 min in the healthy group, while in the elderly group Cmax was 12 at 87 min. Mean absolute bioavailability of the tablet was the same in both groups, 44% for healthy volunteers and 45% for elderly subjects. [Rochdi M et al; Eur J Clin Pharmacol 46 (4): 351-4 (1994). Available from, as of September 29, 2009:] PubMed Abstract
After intravenous administration of (3)H-colchicine to rat, hamster, rabbit and dog (0.2-2 mg/kg), colchicine is widely distributed. high levels have been found in the liver, kidneys, spleen and intestinal tract.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 1.03(2) and a structure estimation method(3), indicates that colchicine is expected to have low mobility in soil(SRC). Volatilization of colchicine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-17 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Colchicine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-11 mm Hg at 25 deg C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2009).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 1.03(2) and a structure estimation method(3), indicates that colchicine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.8X10-17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 2.2(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2009).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), colchicine, which has an estimated vapor pressure of 3.2X10-11 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase colchicine may be removed from the air by wet or dry deposition(SRC). Colchicine contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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