| Identification | Back Directory | [Name]
ALPHA-ERGOCRYPTINE | [CAS]
511-09-1 | [Synonyms]
ergocryptine
ergokryptine
Ergocrypyine
α-Ergocryptine
A-ergocryptine
ALPHA-ERGOCRYPTINE
9,10-Dihydro-&beta
alpha-ergokryptine
ERGOCRYPTINE95%,98%
(R)-9,10-Dihydro-&beta
Ergocryptine
Ergokryptine
Bromocriptine EP Impurity B
ALPHA-ERGOCRYPTINE USP/EP/BP
A-ERGOCRYPTINE ERGOT ALKALOID
Bromocriptine mesilate EP Impurity B
Bromocriptine Impurity 2（Bromocriptine Mesylate EP Impurity B)
12'-Hydroxy-2'-isopropyl-5'α-isobutylergotaman-3',6',18-trione
12'-hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione
12’-hydroxy-2’-(1-methylethyl)-5’-alpha-(2-methylpropyl)ergotaman-3’,6’,18-t
12μ-Hydroxy-2μ-(1-methylethyl)-5μ-α-(2-methylpropyl)ergotaman-3μ,6μ,18-trione
ErgotaMan-3',6',18-trione,12'-hydroxy-2'-(1-Methylethyl)-5'-(2-Methylpropyl)-, (5'a)-
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'α)- | [EINECS(EC#)]
208-121-2 | [Molecular Formula]
C32H41N5O5 | [MDL Number]
MFCD00056790 | [MOL File]
511-09-1.mol | [Molecular Weight]
575.7 |
| Chemical Properties | Back Directory | [Melting point ]
152-154°C | [alpha ]
D20 -120° (pyridine); -198° (chloroform) | [Boiling point ]
636.59°C (rough estimate) | [density ]
1.1762 (rough estimate) | [refractive index ]
1.7500 (estimate) | [storage temp. ]
−20°C
| [solubility ]
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.3 mg/mL
| [form ]
Solid | [pka]
9.61±0.60(Predicted) | [color ]
Pale Yellow to Pale Beige | [Stability:]
Hygroscopic | [InChIKey]
YDOTUXAWKBPQJW-YBALXUQENA-N | [SMILES]
[C@@]12(O)O[C@@](C(C)C)(NC(=O)[C@H]3CN(C4CC5=CNC6=CC=CC(=C56)C4=C3)C)C(=O)N1[C@@H](CC(C)C)C(=O)N1CCCC21 |&1:0,3,10,30,r| |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Solid | [Uses]
An impurity of 2-Bromo α-Ergocriptine Mesylate (B682600). | [Uses]
α-Ergocryptine is an ergopeptine and one of the ergot alkaloids. An impurity of 2-Bromo α-Ergocryptine Mesylate (B682600). | [Definition]
ChEBI: Ergotaman bearing hydroxy, isopropyl, and 2-methylpropyl groups at the 12', 2' and 5' positions, respectively, and oxo groups at positions 3', 6', and 18. It is a natural ergot alkaloid. Ergocryptine discussed in the literature prior to 1967, when b
ta-ergocryptine was separated from alpha-ergocryptine, is now referred to as alpha-ergocryptine. | [General Description]
One of the biologically most important ergot alkaloids is α-ergocryptine. Its semisynthetic derivative, the so-called bromocryptine, is one of the most widely used drugs in this family (e.g., as a prolactin inhibitor or an anti-Parkinsonian)[2]. | [Toxicology]
A study describes the metabolic changes observed in a dietary subacute toxicity experiment with the ergot alkaloid α-ergocryptine in Sprague±Dawley rats. The rats were fed 0, 4, 20, 100 or 500 mg ergocryptine/kg diet for 28±32 days (equal to 0, 0.36, 1.7, 8.9 and 60 mg ergocryptine/kg body weight/day for females and 0, 0.34, 1.4, 6.6 and 44 mg ergocryptine/kg body weight/day for males). Total cholesterol and high-density lipoprotein (HDL)-cholesterol was decreased dose-dependently in females, but the ratio HDL-cholesterol/total cholesterol was only decreased at 20 mg/kg body weight. Triglycerides and glucose concentrations were decreased in the highest dose groups of both sexes. Serum urea concentrations were increased in the 20, 100 and 500 mg/kg dose groups. Insulin, glucagon and liver glycogen were increased in the highest dose group at the end of the study when the animals were allowed to eat prior to blood sampling and necropsy. Prolactin, T4 and FT4 were decreased in the 20, 100 and 500 mg/kg dose groups of both sexes. Follicle-stimulating hormone (FSH) was decreased in the 20, 100 and 500 mg/kg female dose groups and luteinizing hormone (LH) was increased in the 20, 100 and 500 mg/kg male dose groups[1]. | [Purification Methods]
It crystallises with solvent of crystallisation, from acetone, *benzene or methanol. [Stadler et al. Helv Chim Acta 52 1549 1969, Beilstein 25 III/IV 964, 27 II 860.] | [References]
[1] G.B Janssen . “Subacute toxicity of α-ergocryptine in Sprague–Dawley rats. 1: general toxicological effects.” Food and Chemical Toxicology 38 8 (2000): Pages 679-688.
[2] I. Moldvai. “Enantioefficient Synthesis of α-Ergocryptine: First Direct Synthesis of (+)-Lysergic Acid (I).” ChemInform 8 1 (2005).
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