Agroclavine

Title: Agroclavine
CAS Registry Number: 548-42-5
CAS Name: 8,9-Didehydro-6,8-dimethylergoline
Molecular Formula: C16H18N2
Molecular Weight: 238.33
Percent Composition: C 80.63%, H 7.61%, N 11.75%
Literature References: A non-peptide ergot alkaloid obtained from cultures of fungi parasitic on Elymus mollis Trin.: Abe et al., JP 49 178336 (1949 to Takeda), C.A. 45, 6352c (1951); Annu. Rep. Takeda Res. Lab. 10, 145, 167, 171 (1951); JP 54 7498 (1954), C.A. 50, 6000b (1956); US 2835675 (1958). Found in fungi parasitic on Pennisetum typhoideum Rich.: Stoll et al., Helv. Chim. Acta 37, 1815 (1954). Structure and stereochemistry: Schreier, ibid. 41, 1984 (1958). Biosynthesis: Floss et al., J. Am. Chem. Soc. 90, 6500 (1968). Synthesis: Plieninger et al., Ann. 743, 95 (1971). Metabolism: Ramstad, Lloydia 31, 327 (1968).
Properties: Rods from ether, dec 198-203°; needles from acetone, dec 205-206°. [a]D20 -155° (c = 0.9 in chloroform); [a]D20 -182° (c = 0.5 in pyridine). uv max: 225, 284, 293 nm (e 4.47, 3.88, 3.81). Freely sol in alc, chloroform, pyridine; sol in benzene, ether; very slightly sol in water.
Optical Rotation: [a]D20 -155° (c = 0.9 in chloroform); [a]D20 -182° (c = 0.5 in pyridine)
Absorption maximum: uv max: 225, 284, 293 nm (e 4.47, 3.88, 3.81)
Agrocybin Ahistan Ajaconine Ajmaline Ajowan Oil

Agroclavine
Agroclavine.svg
Identifiers
CAS number 548-42-5 N
PubChem 73484
ChemSpider 66176 YesY
ChEBI CHEBI:2519 N
ChEMBL CHEMBL449081 YesY
Jmol-3D images Image 1
Properties
Molecular formula C16H18N2
Molar mass 238.33 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Agroclavine belongs to the group of ergot alkaloids, such as ergotamine.[1] Historically, the main use of argoclavine was to oxidize it to elymoclavine,[citation needed] which can then be used for ergot-based drug synthesis.