Ergocryptine

alpha-Ergocryptine

Identifiers
CAS Number	511-09-1
PubChem	CID 134551
IUPHAR/BPS	271
ChemSpider	118591
ChEMBL	CHEMBL1403281
Chemical data
Formula	C32H41N5O5
Molar mass	575.698 g/mol
SMILES O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3CC(C)C)(NC(=O)[C@@H]7/C=C6/c4cccc5c4c(cn5)C[C@H]6N(C)C7)C(C)C
InChI InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20-,24-,25+,26+,31-,32+/m1/s1 Key:YDOTUXAWKBPQJW-NSLWYYNWSA-N
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Ergocryptine is an ergopeptine and one of the ergot alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine.^[1]

Chemistry

Ergocryptine is a mixture of two very similar compounds, alpha- and beta-ergocryptine.^[2] The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine.

See also

• Dihydroergocryptine

References

1. Kren V., Cvak L. "Ergot: the genus Claviceps". Amsterdam: Harwood Academic Publishers; 1999. p. 399–401
2. Yates, S. G.; Plattner, R. D.; Garner, G. B. (1985). "Detection of ergopeptine alkaloids in endophyte-infected, toxic Ky-31 tall fescue by mass spectrometry/mass spectrometry" (PDF). Journal of Agricultural and Food Chemistry 33 (4): 719. doi:10.1021/jf00064a038.