3-Demethylcolchicine
(Synonyms: 3-去甲秋水仙碱) 目录号 : GC62794
An active metabolite of colchicine
Cas No.:7336-33-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-demethyl Colchicine is an active metabolite of colchicine .1,2 It suppresses antibody production induced by sheep red blood cells in co-culture with isolated mouse spleen cells when used at concentrations ranging from 0.1 to 10 ?g/ml.2 3-demethyl Colchicine (100 ?g/animal) inhibits carrageenan-induced paw edema in rats.3
1.Sch?nharting, M., Mende, G., and Siebert, G.Metabolic transformation of colchicine. II. The metabolism of colchicine by mammalian liver microsomesHoppe Seylers Z. Physiol. Chem.355(11)1391-1399(1974) 2.Sterzl, J., Santav?, F., Sedmera, P., et al.Effect of colchicine derivatives on the antibody response induced in vitroFolia Microbiol. (Praha)27(4)256-266(1982) 3.Sugio, K., Maruyama, M., Tsurufuji, S., et al.Separation of tubulin-binding and anti-inflammatory activity in colchicine analogs and congenersLife Sci.40(1)35-39(1987)
| Cas No. | 7336-33-6 | SDF | |
| 别名 | 3-去甲秋水仙碱 | ||
| 分子式 | C21H23NO6 | 分子量 | 385.41 |
| 溶解度 | DMSO : 100 mg/mL (259.46 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.5946 mL | 12.9732 mL | 25.9464 mL |
| 5 mM | 0.5189 mL | 2.5946 mL | 5.1893 mL |
| 10 mM | 0.2595 mL | 1.2973 mL | 2.5946 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-Demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicines
J Med Chem 1981 Mar;24(3):257-61.PMID:7265112DOI:10.1021/jm00135a005.
A variety of colchicine, demecolcine, and isocolchicine derivatives were examined for their potency in the lymphocytic leukemia P388 screen in mice, for their toxicity in mice, and for their binding to microtubule protein. A qualitatively direct correlation was found between in vivo potency and toxicity; potency appeared to be less well correlated with tubulin binding. The most potent compounds were N-acylated analogues of colchicine and demecolcine. Among the monophenols, only 3-Demethylcolchicine showed an appreciable effect in vitro and in vivo and was less toxic than colchicine. Improved methods were found for the preparation of 3- and 2-demethylcolchicine, which involved the use of 85% phosphoric acid and concentrated sulfuric acid, respectively. Decoupling experiments with 1H NMR proved that the double bond of dehydro-7-deacetamidocolchiceine and its derived tropolonic methyl ethers 24 and 25 was in the 5,6 position, rather than the 6,7 position formerly tentatively assigned.
Isolation and anti-inflammatory activity of colchicinoids from Gloriosa superba seeds
Pharm Biol 2010 Feb;48(2):206-9.PMID:20645842DOI:10.3109/13880200903081770.
Gloriosa superba L. (Liliaceae) seeds, known as "kalihari" (Hindi), were phytochemically investigated for colchicine (well known for gout treatment) and other related alkaloid content. Colchicine, 2- demethylcolchicine, 3-Demethylcolchicine, and N-formyl-N-deacetylcolchicine were alkaloids isolated from the seeds. The isolated samples have been standardized for their purity with respect to the reference standard using HPLC. The structures were confirmed by NMR spectroscopy and were analyzed by spiking them along with colchicine reference by HPLC. The purity of colchicine, 2- demethylcolchicine, 3- demethylcolchicine and N-formyl-N-deacetylcolchicine were 99.82, 96.78, 98.71, and 98.13% respectively. The compounds were subjected to an anti-inflammatory study by using the formaldehyde inflammagen-induced inflammation model. Oral administration of colchicine at 2, 4, and 6 mg/kg body weight resulted in 48.9, 68.7, and 79.1% inhibition respectively, while 30.9% inhibition was seen in the phenylbutazone 100 mg/kg treated group once daily for a period of 4 days. The results clearly indicated that the colchicine is more effective as an anti-inflammatory agent compared with phenylbutazone, the standard drug used in the study, whereas the oral administration of 6 mg/kg body weight of 2- demethylcolchicine, 3-Demethylcolchicine and N-formyl-N-deacetylcolchicine showed very poor activity (41.6, 40.4, and 41.1% activity respectively).
Alkaloids and Phenolics of Colchicum cilicicum1,2
Planta Med 1988 Jun;54(3):243-5.PMID:17265262DOI:10.1055/s-2006-962417.
The distributions of the alkaloids colchicine, 2-demethylcolchicine, 3-Demethylcolchicine, demecolcine, 2-demethyldemecolcine, and 3-demethyldemecolcine in the corms, stems, leaves, flowers, and seeds of COLCHICUM CILICICUM were analysed by HPLC. In addition, the alkaloids cornigerine, N-formyl- N-deacetylcolchicine, N-methyl-demecolcine, beta-lumicolchicine, gamma-lumicolchicine, beta-lumidemecolcine, gamma-lumidemecolcine, and N-ethoxycarbonyldemecolcine were identified, the last named being reported for the first time from a COLCHICUM species. The flavones luteolin and apigenin were isolated and benzoic, 2-hydroxy-6-methoxybenzoic, and vanillic acids were also detected.
Critical review on medicinally potent plant species: Gloriosa superba
Fitoterapia 2011 Apr;82(3):293-301.PMID:21059382DOI:10.1016/j.fitote.2010.11.008.
Gloriosa superba L. is a perennial climber and is used as an ayurvedic medicinal herb to cure diseases in various parts of Africa and Southeast Asia. The plant was under threatened category due to its imprudent harvesting from wild as it is extensively used by medicinal industries for its colchicine content. It also faces a low seed set problem, but due to its industrial demand it is now under cultivation. The plant is used to cure arthritis, gout, rheumatism, inflammation, ulcers, bleeding piles, skin diseases, leprosy, impotency, snakebites, etc. Various compounds have been isolated from the plant parts mainly tubers and seeds, viz colchicine, colchicoside (its semi-synthetic derivative - thiocolchicoside), superbine, gloriosine, lumicolchicine, 3-demethyl-N-deformyl-N-deacetylcolchicine, 3-Demethylcolchicine, N-formyl deacetylcolchicine. In the present review, we have summarized the information concerning the occurrence, botanical description, ethanopharmacology, medicinal uses, biological activities and toxicological studies on this plant.
Separation of tubulin-binding and anti-inflammatory activity in colchicine analogs and congeners
Life Sci 1987 Jan 5;40(1):35-9.PMID:3796211DOI:10.1016/0024-3205(87)90249-9.
The effects of colchicine and its analogs on the carrageenin-induced footpad edema in rats were investigated. The anti-inflammatory effects of colchicine analogs were measured at 3 and 5 hr after the carrageenin injection. Colchicine, 1-demethylcolchicine and 3-Demethylcolchicine markedly inhibited the carrageenin edema whereas 2-demethylcolchicine was much less active. Thiocolchicinoids, having a thiomethyl group at C-10 instead of a methoxy group, were considerably less potent. These results suggest that the presence of methoxy groups at C-2 and C-10 in colchicine is necessary to maintain anti-inflammatory activity. Inactivity of deacetylcolchicine indicates that substitution of the amino group at C-7 with electron withdrawing groups is also important. Significant inhibition of carrageenin edema and strong binding to tubulin in vitro were manifested by colchicine, 3-Demethylcolchicine, N-butyryldeacetylcolchicine and colchifoline. On the other hand, N-carbethoxydeacetylcolchicine which did bind well to tubulin, did not show much effect on the carrageenin edema. These results suggest that the anti-inflammatory action of colchicinoids may not be regulated through the microtubule system.