Ergometrine

Legality: DEA Listed Chemicals

Production of this substance may be illegal in some jurisdictions under certain circumstances.

21CFR1310.02 a & b

In 1995/6, two lists were created "List I" and "List II", for which commercial manufacturers and distributors must register, and for which possession with the intent to manufacture illegal substances (such as methamphetamine, ecstasy, etc) is illegal. On these a few dozen "precursor" compounds commonly used in the manufacture of illegal drugs.

Bottom line: Do not produce this chemical without checking to make sure that you may do so legally.

 

 

Ergometrine
aka Ergonovine
DEA LIST I/II SUBSTANCE

Chemical formula	C19H23N3O2
Molar Mass(g/mol)	325.41
Melting Point(°C)	150-152
LD50	8.2mg/kg (mouse)
NFPA 704	0 0 0

Uses

Primary

• Pharm: WHO LEM component

Natural occurrence

• Does occur naturally in the growths of claviceps purpurea.

Production

Extraction

from defatted ergot powder

A general process to extract ergomerine from "defatted ergot powder" with a yield of 0.82g ergometrine from 10kg of powder was published in 1935.

1. Initial Extraction into ergometrine sulfate(aq)
   1. Prepare "defatted ergot powder"
   2. Mix thoroughly with hot, dilute sulfuric acid

      Ergometrine(aq) -> ergometrine sulfate(aq)

   3. filter and discard residue (primarily undissolved organic material)
2. Extract into ethanol and thence ergometrine(tcm)
   1. Basify with excess barium hydroxide

      ergometrine sulfate(aq) → ergometrine(aq)

   2. filter and discard residue (primarily barium sulfate)
   3. bubble carbon dioxide through the filtrate
   4. filter and discard residue (primarily barium carbonate)
   5. evaporate to "a small volume"
   6. add pure ethanol, resulting in a "sticky" precipitate
   7. filter and discard residue (sticky precipitate)
   8. Mix thoroughly with trichloromethane

      Ergometrine(aq) → Ergometrine(tcm)

   9. Separate and discard aqueous layer
3. Extract into ergometrine sulfate(aq)
   1. Mix thoroughly with hot dilute sulfuric acid

      Ergometrine(tcm) -> ergometrine sulfate(aq)

   2. Separate and discard chloroform layer
4. Extract into ergometrine (tcm)

   Basically repeating step 2 without the ethanol "throw down"

   1. Basify with excess barium hydroxide

      Ergometrine sulfate(aq) → ergometrine(aq)

   2. filter and discard residue (primarily barium sulfate)
   3. bubble carbon dioxide through the filtrate
   4. filter and discard residue (primarily barium carbonate)
   5. Mix thoroughly with trichloromethane

      Ergometrine(aq) → Ergometrine(tcm)

   6. Evaporate to dryness (resinous material containing ergometrine crystals
5. Dissolve and remove resinous material
   1. Slowly and incrementally add trichloromethane sufficient to dissolve the resinous material, but leaving the less-soluble ergometrine crystals undissolved.
   2. Filter and discard filtrate
6. Recrystallize from benzene

Preparations

• Ergotamine maleate (ergotamine's salt with maleic acid is more stable than the free base, and is the usual injectable form

  In human medicine, it is used orally and parenterally in the prevention and treatment of postpartum

haemorrhage caused by uterine atony and for the stimulation of uterine involution. Usual oral doses are 500 μg 3 times daily up to 1.8 mg daily (approximately 0.03 mg/kg bw)

Testing

• Moderately soluble in trichloromethane, benzene, and dichloroethylene

  recrystallization from any of these is possible.

• Very soluble in methanol, ethanol, propanone, and ethyl acetate

  evaporation from any solution of these give a gum-like residue

• Oxidizes (turns brown) on exposure to atmosphere
• 0.1% solution in trichloromethane gives an optical rotation of approximately -45°

Purification

Recrystallize from trichloromethane, benzene or dichloroethylene, giving needle-like crystals

See Also

• US patent 2809920 "Process for the preparation of ergotamine, ergotaminine and ergometrine by saprophytic culture of ergot (claviceps purpurea) in vitro and isolation of the alkaloids thus produced"
  Link courtesy Google