α-Ergocryptine Chemical Properties

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|

Safety Information

Hazard Codes 

Xn

Risk Statements 

62

Safety Statements 

36/37

RIDADR 

UN 1544 6.1/PG 3

WGK Germany 

3

RTECS 

KE1400000

HazardClass 

6.1(b)

PackingGroup 

III

α-Ergocryptine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

α-Ergocryptine is an ergopeptine and one of the ergot alkaloids. An impurity of 2-Bromo α-Ergocryptine Mesylate (B682600).

Uses

An impurity of 2-Bromo α-Ergocriptine 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).

α-Ergocryptine(511-09-1)Related Product Information

• Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (2'β,5'α,8α)- (9CI)
• BroMocriptine IMpurity G
• BroMocriptine-13C-d3
• BroMocriptine IMpurity F
• Ergoline-8-carboxylic acid, 2-bromo-9,10-didehydro-6-methyl-, (8β)-
• Ergocryptine, 2-bromo- (8CI),2-bromo-alpha-ergocryptin
• (8S)-2-BroMo α-Ergocryptine
• Bromocriptine mesylate
• BroMocriptine IMpurity E
• beta-ergocryptine
• Bromocriptine Impurity 2
• Bromocriptine Impurity A (Mixture of Diastereomers)
• DIHYDROERGOCRISTINE MESYLATE
• ERGTOXIN
• ALPHA-ERGOCRYPTINE
• Mergocriptine
• 1-Bromo-α-ergocryptine methane Sulfonate
• ergocryptine methanesulfonate