511-09-1

Basic information

• Product Name: ALPHA-ERGOCRYPTINE
• Synonyms: 12’-hydroxy-2’-(1-methylethyl)-5’-alpha-(2-methylpropyl)ergotaman-3’,6’,18-t;alpha-ergokryptine;ergocryptine;ALPHA-ERGOCRYPTINE;A-ergocryptine;12'-hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione;A-ERGOCRYPTINE ERGOT ALKALOID;ERGOCRYPTINE95%,98%
• CAS NO: 511-09-1
• Molecular Formula: C₃₂H₄₁N₅O₅
• Molecular Weight: 575.7
• EINECS: 208-121-2
• Product Categories: Aromatics;Heterocycles;Impurities;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 511-09-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 152-154°C
• Boiling Point: 636.59°C (rough estimate)
• Flash Point: 475°C
• Appearance: /
• Density: 1.1762 (rough estimate)
• Vapor Pressure: 1.16E-31mmHg at 25°C
• Refractive Index: 1.7500 (estimate)
• Storage Temp.: −20°C
• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.3 mg/mL
• PKA: 9.61±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: ALPHA-ERGOCRYPTINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-ERGOCRYPTINE(511-09-1)
• EPA Substance Registry System: ALPHA-ERGOCRYPTINE(511-09-1)

Safety Data

• Hazard Codes: Xn
• Statements: 62
• Safety Statements: 36/37
• RIDADR: UN 1544 6.1/PG 3
• WGK Germany: 3
• RTECS: KE1400000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 511-09-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 511-09-1 differently. You can refer to the following data:
1. α-Ergocryptine is an ergopeptine and one of the ergot alkaloids. An impurity of 2-Bromo α-Ergocryptine Mesylate (B682600).
2. 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.

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.]

InChI:InChI=1/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

Synthetic route

α-ergocryptine (511-09-1) → Dihydroergocryptine (25447-66-9)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 35℃; for 3h; Inert atmosphere;	95%

α-ergocryptine (511-09-1) → Bromocriptine (25614-03-3)

Conditions	Yield
With bromodimethylsulfoxonium bromide In dimethyl sulfoxide for 0.166667h; Ambient temperature;	93%
With pyridazinium bromide; 3-bromo-6-chloro-2-methylimidazo In dichloromethane for 0.0333333h; Ambient temperature;	75%
With ammonium hydroxide; sodium hydroxide In dichloromethane; di-isopropyl ether; water; hydrogen bromide; dimethyl sulfoxide

α-ergocryptine (511-09-1) → (6aR,9R)-5a-Hydroxy-7-methyl-5-oxo-4,5,5a,6,6a,7,8,9-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide + Bromocriptine (25614-03-3)

Conditions	Yield
With water; hydrogen bromide In dimethyl sulfoxide for 0.333333h; Product distribution; Ambient temperature; halogenation of indole alkaloids with various halogenated agents;	A 8% B 72%

α-ergocryptine (511-09-1) → 2,3-dihydro-2-oxo-α-ergokryptine

Conditions	Yield
With water; bromine In tetrahydrofuran; dichloromethane for 0.0166667h; Ambient temperature;	64%

α-ergocryptine (511-09-1) → 6'-Deoxo-α-ergokryptine

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -5℃; for 1h;	51%

α-ergocryptine (511-09-1) → alpha-Ergocryptinine (511-10-4)

Conditions	Yield
In methanol at 19.9℃; Rate constant; epimerization at the C-8; var. solvents, var. pH;

2-bromo-α-ergocryptine base + α-ergocryptine (511-09-1) → Bromocriptinmesilat

trimethylsilyl bromide (2857-97-8) + α-ergocryptine (511-09-1) → Bromocriptine (25614-03-3)

Conditions	Yield
With ammonium hydroxide; sodium chloride In ice-water; dichloromethane; di-isopropyl ether; dimethyl sulfoxide; ethyl acetate

α-ergocryptine phosphate + α-ergocryptinine base + trimethylsilyl bromide (2857-97-8) + α-ergocryptine (511-09-1) → Bromocriptine (25614-03-3)

Conditions	Yield
	4.7 g (0.007243 mole, 85%)
	4.7 g (0.007243 mole, 85%)

α-ergocryptinine base + trimethylsilyl bromide (2857-97-8) + α-ergocryptine (511-09-1) → Bromocriptine (25614-03-3)

Conditions	Yield
With ammonium hydroxide; sodium chloride In ice-water; dimethyl sulfoxide; ethyl acetate	mole, 87%)
With ammonium hydroxide; sodium chloride In ice-water; dimethyl sulfoxide; ethyl acetate	6.3 g (0.00967 mole, 87%)

methanol (67-56-1) + 2-chloro-1,3-dithiane (57529-04-1) + α-ergocryptine (511-09-1) → 2-(1,3-dithian-2-yl)-α-ergocryptine (77528-04-2)

Conditions	Yield
With sodium carbonate In dichloromethane; chloroform

diispropyl ether + trimethylsilyl bromide (2857-97-8) + α-ergocryptine (511-09-1) → Bromocriptine (25614-03-3)

Conditions	Yield
With ammonium hydroxide; sodium chloride In ice-water; dichloromethane; dimethyl sulfoxide; ethyl acetate

Downstream Products

• 511-10-4 alpha-Ergocryptinine 
• 25447-66-9 Dihydroergocryptine 
• 25614-03-3 Bromocriptine 
• 25614-03-3 Bromocriptine 
• 675-20-7 piperidin-2-one 
• 25614-03-3 2-bromo-α-ergocryptine 

Relevant articles and documents

The synthesis of alkaloids of the ergotoxin group. 70. Section on ergot alkaloids

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