Colchicin
Colchicin · Colchlcine · (S)-colchicine · Colchicine (contains 5% Ethyl Acetate at maximum) · (S)-N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO[A]HEPTALEN-7-YL)ACETAMIDE · nsc757 · COLCIN · NSC 757
Identifikatoren & physikalische Daten
| CAS No. | 64-86-8 |
|---|---|
| Summenformel | C22H25NO6 |
| Durchschnittliche Molmasse | 399,4 g/mol |
| Monoisotopische Masse | 399,16818752 g/mol |
| SMILES | COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1[C@@H](NC(C)=O)CC2 |
| InChIKey | IAKHMKGGTNLKSZ-INIZCTEOSA-N |
| PubChem CID | 6167 |
| ChEMBL | CHEMBL107 |
| ChEBI | CHEBI:27882 |
| EC No. | 200-598-5 |
| DTXSID | DTXSID5024845 |
| Lokaler Name | Colchicin |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 83,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 29 |
| Formalladung | 0 |
| Komplexität | 740 |
| Stoffklassen | Teratogens-> NIOSH Emergency Response Categories |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| pH | pH of 0.5% solution: 5.9 |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | log Kow = 1.03 |
| Geruch | Odorless or nearly so |
| Color/Form | Pale yellow scales or powderpale yellow needles when crystallized from ethyl acetateYellow plates from water + 1/2 mol of water of crystallizationyellow crystals from benzene |
| Löslichkeit | greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)1 g dissolves in 22 mL water, 220 mL ether, 100 mL benzenefreely sol in alcohol or chloroformpractically insoluble in petroleum etherSOL IN METHANOLSLIGHTLY SOL IN CARBON TETRACHLORIDEAt 25 °C, 4.5 g/100 g waterH2O: 10 mg/mL45 g/L (20 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanAntigout AgentsAntimitotic AgentsGout SuppressantsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicinePharmaceuticals |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 407 °C @760 [mm Hg]522.37°C (rough estimate) |
| Decomposition | When heated to decomposition, colchicine emits toxic fumes of carbon monoxide, carbon dioxide, and nitrogen oxides. |
| Schmelzpunkt | 150-160 °C (dec.)(lit.) |
| Dichte | 1.2770 (rough estimate) |
| Brechungsindex | 1.5614 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 12.36(at 20℃) |
| Farbe | white to yellow with a green cast |
| Merck | 14,2471 |
| BRN | 2228813 |
| Henry-Konstante | 5.5×1011 mol/(m3Pa) at 25℃, HSDB (2015) |
| BCS Class | 3 |
| Stabilität | Stable. Light sensitive. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | agriculture |
| 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(C)=O |
| LogP (Verteilungskoeffizient) | 1.300 |
| CAS Datenbank | 64-86-8(CAS DataBase Reference) |
| NIST chemische Informationen | Colchicine(64-86-8) |
| EPA chemische Informationen | Colchicine (64-86-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)H300+H330 (25.9%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oralacute toxicity, inhalation]P203, P260, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Hazard Traits - Developmental ToxicityGenotoxicityReproductive ToxicityStatus: Active Update: 29-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1277Colchicine: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-: Human health tier I assessment- Indoor Air: Colchicine can be released into indoor air as fine particles or liquid spray (aerosol). |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Stable. (EPA, 1998) |
| Brandpotenzial | Slight. |
| Gesundheitsgefahren | It is classified as super toxic. Probable oral lethal dose in humans is less than 5 mg/kg, i.e. less than 7 drops for a 70 kg (150 lb.) person. Death results from respiratory arrest. The fatal dose varies considerablyas little as 7 mg of colchicine has proved fatal. (EPA, 1998) |
| FDA-Anforderungen | 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. |
Anwendungen & Verwendung
Beschreibung
Colchicine is a pale-yellow powder that is obtained from various species of Colchicum, primarily Colchicum autumnale L. Its total chemical synthesis has been achieved, but the primary source of colchicine currently remains alcohol extraction of the alkaloid from the corm and seed of C. autumnale L. It darkens on exposure to light and possesses
History
Meadow saffron (Colchicum) is recorded to treat rheumatic swelling on ancient Egyptian medical papyrus in 1500 B.C.. According to De Materia Medica written by Pedanius Dioscorides in the first century, extract of Meadow saffron is used in treating gout. London Pharmacopoeia in 1618 recorded that colchicine is also applied to treat gout.In 1820, the ingredient was first isolated by the French chemist P.S. Pelletier and J.B. Caventou. In 1833, it was purified and named by Geiger. Michael Dewar guessed that there are two seven-membered rings in colchicine in 1945. Murray Vernon King et al. determined the structure of colchicine by X-ray diffraction in 1952. In 1959, Albert Eschenmoser integrated the product successfullyColchicine tablet and raw material are approved mostly in domestic in 2010. The tablet produced by Taiwan manufacturers is approved for being listed in mainland of China in 2012. The raw material made by Indian obtained the approval in 2013. There are three kinds of colchicine approved by FDA: with the combination of probenecid, it is prior to be approved. The others are tablet (2009) and capsule (2014).
Verwenden
Colchicine is present in the poisonous autumncrocus (meadow saffron). It is the major alkaloid of Colchicum autumnale L. and Liliaceae. It was used in poison potions in theancient kingdom of Colchis (Greece). It isused therapeutically as an antineoplast, for thesuppression of gout, and in the treatment ofMediterranean fever. It is used in plant studiesfor doubling chromosome groups.