Colchicine
Also known as Colchisol, Colchineos, Colchicinum
Key facts
What buyers check first
- Appearance
- Pale yellow scales or powder, pale yellow needles when crystallized from ethyl acetate
- Melting point
- 142 to 150
- Boiling point
- 407 °C
- Solubility
- 1 g dissolves in 22 mL water, 220 mL ether, 100 mL benzene, freely sol in alcohol or chl…
- HS code
- 293979
- Category
- Analgesics and anti-inflammatories
- UN number
- UN 1544
What is Colchicine?
Plain description, key identifiers and synonyms
(S)-colchicine is a colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions. It has a role as a mutagen, a gout suppressant and an anti-inflammatory agent. It is an alkaloid and a colchicine. It is an enantiomer of a (R)-colchicine.
Colchicine is a medication most commonly used to treat gout.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
- CAS number
- 64-86-8 CAS number cross-checkedOther or deprecated CAS: 30512-31-3
- EC number
- 200-598-5
- Molecular formula
- C22H25NO6
- UNII
- 7JX9WZ3SJ5, SML2Y3J35T
- MDL number
- MFCD00078484
- InChIKey
- IAKHMKGGTNLKSZ-INIZCTEOSA-N
- 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
- Canonical SMILES
- COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1C(NC(C)=O)CC2
- Isomeric SMILES
- CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Synonyms
- Colchisol
- Colchineos
- Colchicinum
- Colchicina
- Colcrys
- (-)-colchicine
- Mitigare
- 7-alpha-H-Colchicine
- Lodoco
- (S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
- N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
- Colchcine
- N-Acetyl trimethylcolchicinic acid methylether
- Gloperba
- Myinfla
- Mitigare component colchicine
- Benzo(a)heptalen-9(5H)-one, 7-acetamido-6,7-dihydro-1,2,3,10-tetramethoxy-
- Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
- Acetamide, N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-
- Acetamide, N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-
- (S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide
- N-((7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo(a)heptalen-7-yl)acetamide
- N-((7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo(d)heptalen-7-yl)acetamide
- N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]acetamide
- Colchicum
Show all 38 synonymsShow fewer synonyms
- Colcigel
- COLCHICINUM 4x
- Colchicine Tablets 0.5 mg
- N-(3,4,5,14-tetramethoxy-13-oxotricyclo(9.5.0.02,7)hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl)acetamide
- Benzo(a)heptalene, acetamide deriv.
- Colsaloid
- Condylon
- Colcin
- Colchicin
- 7alphaH-Colchicine
- Colchicine EP Impurity B
- Kolkicin
- Goutnil
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
| Appearance | Pale yellow scales or powder, pale yellow needles when crystallized from ethyl acetateexp.Measured value |
|---|---|
| Odour | Odorless or nearly soexp.Measured value |
| Melting point | 142 to 150exp.Measured value |
| Boiling point | 407 °Cexp.Measured value |
| Solubility | 1 g dissolves in 22 mL water, 220 mL ether, 100 mL benzene, freely sol in alcohol or chloroform, practically insoluble in petroleum etherexp.Measured value |
| Vapour pressure | 0.00001 [mm Hg] @25 °Cexp.Measured value |
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 399.44 g/molcalc.Computed value |
|---|---|
| Exact mass | 399.1682 Dacalc.Computed value |
| LogP (octanol/water) | 2.87calc.Computed value |
| Topological polar surface area | 83.09 Ųcalc.Computed value |
| Hydrogen bond donors | 1calc.Computed value |
| Hydrogen bond acceptors | 6calc.Computed value |
| Rotatable bonds | 5calc.Computed value |
| Heavy atoms | 29calc.Computed value |
| Rings | 3calc.Computed value |
| Aromatic rings | 2calc.Computed value |
| Fraction sp3 carbons | 0.36calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 1calc.Computed value |
| Lipinski rule of five | Passes (0 violations)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
Safety and hazards
GHS classification summary, not a safety data sheet
Hazard statements
- H300Fatal if swallowed.
- H340May cause genetic defects.
Precautionary statements (10)
- P203Obtain, read and follow all safety instructions before use.
- P264Wash skin thoroughly after handling.
- P270Do not eat, drink or smoke when using this product.
- P280Wear protective gloves, protective clothing, eye protection and face protection.
- P301 + P316If swallowed: Get emergency medical help immediately.
- P318If exposed or concerned, get medical advice.
- P321Specific treatment (see supplemental first aid instructions on the label).
- P330Rinse mouth.
- P405Store locked up.
- P501Dispose of contents and container in accordance with local regulations.
- UN number
- UN 1544
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Full safety data and first aidColchicine suppliers
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Where suppliers are based
135 suppliers in 27 countries
- United States35
- India27
- China26
- Germany7
- United Kingdom3
- Ukraine3
- and 21 more countries
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Colchicine price
Indicative price range per kg from live supplier offers
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Uses and applications
What the substance is used for, by industry and function
In research in plant genetics (for doubling chromosomes).
To induce chromosome doubling in plants, phytopathology.
Relieves acute attacks of gout.
Therapeutic category: Gout suppressant. Treatment of Familial Mediterranean Fever.
Colchicine is a highly toxic plant hormone that is used medically in the treatment of gout and in scientific research. Colchicine stops the process of cell division (it is an antimitotic agent). Exposure to colchicine can be fatal in very small doses (e.g., 7 to 65 mg). Colchicine is derived from the meadow saffron or autumn crocus plant (Colchicum autumnale), which is locally abundant in meadows throughout most of Europe and has become naturalized in parts of North America. It can also be found in the tubers of the Glory Lily (Gloriosa superba) found primarily in Florida. It is odorless or nearly so and has a very bitter taste. It is produced in tablets, granules, and ampules of sterile solution. It has uses in the production of legitimate and illicit plant production.
Use classes: Pharmaceuticals.
Industries and functions
Pharmacological actions
- Gout Suppressants
- Tubulin Modulators
Roles
- aetiopathogenetic role
- anti-inflammatory agent
- antimitotic
- antirheumatic drug
- eukaryotic metabolite
- genotoxin
- gout suppressant
- metabolite
- microtubule-destabilising agent
- mutagen
- pharmaceutical
- plant metabolite
- tubulin modulator
Pharmacology
Colchicine is an Alkaloid.
How it is made
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.
Read more
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.
Regulatory status
Inventories, regulations and trade controls that list this substance
Europe
- EU harmonised classification (CLP Annex VI)Index no: 614-005-00-6
Health and food
- EU Cosmetics Regulation Annex II, prohibited in cosmeticsName: Colchicine, its salts and derivatives, Ref no: 102, Annex ref: II/102
- Active ingredient in FDA approved drug labels
United States
- TSCA inventory (USA)Status: Active in US commerce
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Colchicine is traded under.
Alkaloids of vegetal origin, other than cocaine, ecgonine, salts, esters and other derivatives, not elsewhere…
- Switzerland * partner reported25.3%
- Germany21.4%
- India * partner reported14.9%
- United States20.9%
- Germany14.7%
- Italy14.6%
* Partner reported figures, a lower bound.
The HS code shown for Colchicine is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Related chemicals
Parent and salt forms, stereoisomers, similar structures and isomers
Salt and hydrate forms
Records that share this compound as their parent
Stereoisomers and isotopic forms
Same connectivity, different stereochemistry or isotopes (same InChIKey skeleton)
Similar structures
Nearest neighbours by Morgan fingerprint Tanimoto similarity
Same formula isomers
Different compounds that share this molecular formula
![N-[(7S,7bS,10aR)-5,6,7,7b,8,10a-Hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl]acetamide chemical structure, C22H25NO6](/s/VKPVZFOUXUQJMW-LXIYXOSZSA-N.svg)
![3-[(2,5-Dimethoxyphenyl)-hydroxymethyl]-4-(morpholin-4-ylmethyl)-1-benzofuran-5-ol chemical structure, C22H25NO6, CAS 382635-98-5](/s/OYQPVPVZRXYJSS-UHFFFAOYSA-N.svg)
![[2-Oxo-2-(1-phenylethylamino)ethyl] (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate chemical structure, C22H25NO6, CAS 729574-89-4](/s/ITLVAKHTOVQVSL-ZHACJKMWSA-N.svg)
Frequently asked questions
Quick answers about Colchicine, based on the data on this page
What is Colchicine?
What is the CAS number of Colchicine?
What is the molecular formula and weight of Colchicine?
What is Colchicine used for?
Is Colchicine hazardous?
What is the HS code of Colchicine?
Where can I buy Colchicine?
Where can I buy Colchicine in India?
What is the price of Colchicine?
Guides for buyers
Practical guides that help when you source, ship or handle Colchicine
- Article, QualityPharma grades explained: IP vs BP vs USP vs EPWhat the Indian, British, US and European pharmacopoeias are, how their monographs differ, what multi grade claims mean and why a grade alone does not make a product fit for medicines.Read
- Guide, SafetyHow to read a safety data sheet in 10 minutesA section by section method to pull the essentials out of any 16 section SDS: identity, hazards, composition, storage, PPE, properties, transport and emergency measures.Read
- Guide, Trade and logisticsShipping dangerous goods: UN numbers, classes and packing groupsHow the UN dangerous goods system works for chemicals, from the nine classes and UN numbers to packing groups, UN packaging marks, labels, documents and segregation.Read
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