Ergocristine

Title: Ergocristine
CAS Registry Number: 511-08-0
CAS Name: (5¢a)-12¢-Hydroxy-2¢-(1-methylethyl)-5¢-(phenylmethyl)ergotaman-3¢,6¢,18-trione
Molecular Formula: C35H39N5O5
Molecular Weight: 609.71
Percent Composition: C 68.95%, H 6.45%, N 11.49%, O 13.12%
Literature References: Natural ergot alkaloid derived from lysergic acid; a member of the ergotoxine group. Isoln from ergot: Stoll, Burckhardt, Z. Physiol. Chem. 250, 1 (1937); Stoll, Hofmann, Helv. Chim. Acta 26, 1570 (1943). Structure: Stoll et al., ibid. 34, 1544 (1951). Separation and purification: Stoll, Hofmann, US 2447214 (1948 to Sandoz). Synthesis: Stadler et al., Helv. Chim. Acta 52, 1549 (1969).
Properties: Orthorhombic crystals with 2C6H6 from benzene. mp 155-157° (dec) (solvent-free base). [a]D20 -183° (chloroform). Very sol in ethyl and methyl alcohol, acetone, chloroform, ethyl acetate. Slightly sol in ether. Practically insol in water, petr ether.
Melting point: mp 155-157° (dec) (solvent-free base)
Optical Rotation: [a]D20 -183° (chloroform)
Derivative Type: Phosphate
CAS Registry Number: 6424-36-8
Properties: Crystals, dec 195°.
Derivative Type: Ethanesulfonate
CAS Registry Number: 6055-56-7
Properties: Crystals, dec 207°.
Derivative Type: 8a-isomer
CAS Registry Number: 511-07-9
Additional Names: Ergocristinine
Properties: Crystallizes solvent-free, unlike ergocristine which tends to retain the solvent of crystn. Long prisms from abs alc, mp 226° (dec). [a]D20 +366° (c = 0.68 in chloroform); +471° (c = 0.35 in pyridine). uv max (methanol/methylene chloride): 313 nm (log e 3.96). Much less sol than ergocristine. Does not seem to form salts.
Melting point: mp 226° (dec)
Optical Rotation: [a]D20 +366° (c = 0.68 in chloroform); +471° (c = 0.35 in pyridine)
Absorption maximum: uv max (methanol/methylene chloride): 313 nm (log e 3.96)
Ergocryptine Ergocryptinine Ergoflavin Ergoloid Mesylates Ergometrinine

Ergocristine
Ergocristine.svg
Clinical data
Legal status Schedule 1 (US)
Identifiers
CAS number 511-08-0 YesY
ATC code  ?
PubChem CID 31116
ChemSpider 28873 N
ChEMBL CHEMBL446315 N
Chemical data
Formula C35H39N5O5 
Mol. mass 609.714 g/mol
 N (what is this?)  (verify)

Ergocristine is an ergopeptine and one of the ergot alkaloids. As of February 24, 2010 Ergocrisine has been federally scheduled. Because of the existing Controlled Substance Act regulatory controls on the LSD precursors lysergic acid, lysergic acid amide, ergotamine, and ergonovine, clandestine laboratory operators have sought uncontrolled sources of precursor material for the production of LSD. This has led to the illicit utilization of the precursor chemical ergocristine as a direct substitute for ergotamine and ergonovine for the illicit production of LSD. In fact, the largest clandestine LSD laboratory ever, William Leonard Pickard and Clyde Apperson, that was seized by the DEA utilized ergocristine as the LSD precursor. Recipes documenting procedures for utilizing ergocristine in LSD synthesis are easily found on the Internet.

The DEA determined that ergocristine was readily available from commercial chemical suppliers. DEA had identified at least three suppliers of ergocristine, of which one distributor is located domestically; the other two are based in Germany and the Czech Republic.[1][2]