Ergocryptines

Mixture of dihydroergocornine mesylate, C 2H45N OgS dihydroergocristine mesylate, C H N OgS and dihydro-(3-ergocryptine mesylate,... 

A solution of 3.4 grams of N-bromosuccinimide in 60 cc of absolute dioxane is added drop wise in the dark, during the course of 5 minutes, to a stirred solution, heated to 60°C, of 9.2 grams of ergocryptine in 180 cc of absolute dioxane. The reaction mixture is stirred at this temperature for 70 minutes and is concentrated to a syrup-like consistency in a rotary evaporator at a bath temperature of 50°C. The reaction mixture is subsequently diluted with 300 cc of methylene chloride, is covered with a layer of about 200 cc of a 2N sodium carbonate solution in a separating funnel and is shaken thoroughly. The aqueous phase is extracted thrice with 100 cc amounts of methylene chloride. The combined... 

Epoxypropyl)-2-methyl-5-nitroimidazole Ornidazole Ergocryptine Bromocriptine Erythromycin... 

The technical aspect of 2-bromo-a-ergocryptine synthesis, including the characterisation and significance of the impurities obtained in the production process, were reviewed. In the continuation new ergolene and ergoline compounds were synthesized and tested for the pharmacological activity. 

Today, 2-bromo-a-ergocryptine (bromocriptine) is the second (after dihydroergotoxine) most extensively used compound from the group of ergot alkaloids. 

Bromination of a-ergocriptine 2 with commercial N-bromosuccinimide (NBS) can lead to the formation of traces of a mysterious by-product, finally identified as 2-chloro-a-ergocryptine 4. Investigation of NBS indicated that it contains up to 1.5 % of chlorine (probably as N-chloro-succinimide, NCS). This chlorination occurs only in the presence of NBS, never with NCS alone ... 

Ergocomine lb 243 Ergocristine lb 245,348 Ergocryptine lb 379 Ergoline carboxylic acids lb 243 Ergometrine lb 243,252,440,444 Ergosterol la 351... 

Bromocriptine mesilate is 2-bromo-a-ergocryptine methane-sulphonate or 2-bromo-12 -hydroxy-2,-(l-methylethyl)-5 -(2-methylpropyl-5 a-ergotaman-3, 6, 18-trione methanesulphonate or Bromocriptinum (INN). It is the active ingredient in Parlodel dosage forms. 

Theoretically, with 6 chiral centers within the molecule (at 6, 9, 2, 5, 11 and 12 positions) 64 diastereomeric forms are possible. However, bromocriptine is sterically well defined at all of these positions, as it is derived from the naturally occurring a-ergocryptine. 

For the specific rotation of 2-bromo-a-ergocryptine and -inine bases see (11). 

Bromocriptine base is manufactured by bromination of a-ergocryptine with N-bromosuccinimide in dioxane solution. 

The compounds separated are visualized by uv at 254 and 366 nm, respectively, and by iodine vapour. Rf of bromocriptine is 0.27. The potential by-products yield spots at R 1.5 (2-bromo-a-ergocryptinine), and 0.55 (a-ergocryptine). 2-Bromo-lysergic acid remains at the starting point. 

Key 1 = dodecylbenzene, 2 = bromocriptinine, 3 = a-ergocryp-tinine, 4 = bromocriptine, 5 = a-ergocryptine (precursor). 

Medina, D. (1977). Himor formation in preneoplastic mammary nodule lines in mice treated with nafoxidine, testosterone, and 2-bromo-o(-ergocryptine, J. NatL Cancer Inst. 58,1107. 

Dihydroergotoxine, a mixture of dihydro-K-ergocryptine and three similar dihydrogenated peptide ergot alkaloids (ergoloid mesylates), has been promoted for many years for the relief of senility and more recently for the treatment of Alzheimer s dementia. There is no useful evidence that this drug has significant benefit. 

Ergocryptine [511-09-1] M 575.7, m 212-214 . Crystd with solvent of crystn, from acetone, benzene or methanol. 

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