Ergotamine Tartrate

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Ergotamine Tartrate

(C33H 35N5O5)2C4 H6O6

1313.41

Ergotaman-3' ,6' ,18-trione, 12' -hydroxy-2' -methyl-5' -(phenylmethyl)-, (5' )-,[R-(R*,R*)]-2,3dihydroxybutanedioate (2:1) (salt).
Ergotamine tartrate (2:1) (salt)
[379-79-3].

Ergotamine Tartrate contains not less than 97.0 percent and not more
than 100.5 percent of (C33H35 N5O5)2C4H6O6, calculated on the dried basis.
Packaging and storage Preserve in well-closed, light-resistant containers in a cold place.
USP Reference standards 11
USP Ergotamine Tartrate RS.
Identification The chromatogram of the test solution prepared as directed in the test for
Related alkaloids exhibits its principal fluorescent spot and principal blue spot at the same R value
as the principal spot of Standard solution A.
F

Specific rotation

781S [NOTEFor this test, use chloroform from which any alcohol

present has been removed by prior washing with water.] Dissolve about 350 mg in 25 mL of tartaric
acid solution (1 in 100) contained in a separator, then add 500 mg of sodium bicarbonate, and mix
gently but thoroughly. Add 10 mL of chloroform, shake vigorously, and after the layers have
separated draw off the chloroform phase through a small filter, previously moistened with
chloroform, into a 50-mL volumetric flask. Rapidly continue the extraction with three 10-mL portions
of chloroform, passing the extracts through the same filter. Place the flask in a bath at 20 for 10
minutes. Adjust the volume of extract to 50.0 mL at 20 by the addition of chloroform. Mix the
solution, and determine the angular rotation at 20 . Determine the concentration of ergotamine in
the chloroform solution by evaporating a 25.0-mL aliquot of the solution on a rotary evaporator to
dryness, maintaining the temperature of the bath below 45 . Dissolve the residue in 25 mL of
glacial acetic acid, add 1 drop of crystal violet TS, and titrate with 0.05 N perchloric acid VS to an
emerald-green endpoint. Perform a blank determination, and make any necessary correction. Each
mL of 0.05 N perchloric acid is equivalent to 29.08 mg of C33 H35N5 O5. From the angular rotation of
the solution and the concentration of ergotamine base, calculate the specific rotation of the base:
between

155 and

165 .

Loss on drying 731 Dry about 100 mg, accurately weighed, in vacuum at 60 for 4 hours: it
loses not more than 5.0% of its weight.
Related alkaloids [NOTEConduct this test without exposure to daylight and with the minimum
necessary exposure to artificial light.]
Solvent mixture Mix 9 volumes of chloroform with 1 volume of methanol.
Standard preparation and Standard dilutionsPrepare a solution of USP Ergotamine Tartrate RS
in Solvent mixture to contain 10.0 mg per mL (Standard preparation). Prepare a series of dilutions
of the Standard preparation in Solvent mixture to contain 0.2 mg, 0.1 mg, 0.05 mg, and 0.025 mg
per mL (Standard dilutions) corresponding to 2.0%, 1.0%, 0.5%, and 0.25% of the Standard
preparation, respectively.
Test preparation Dissolve 50.0 mg of Ergotamine Tartrate in 5.0 mL of Solvent mixture.
Procedure In a suitable chromatographic chamber arranged for thin-layer chromatography (see
Chromatography 621 ) place a volume of a solvent system consisting of ether,
dimethylformamide, chloroform, and dehydrated alcohol (70:15:10:5). Line the chamber with filter
paper, and allow it to equilibrate for 15 minutes. Apply 5-L portions of the Test preparation, the
Standard preparation, and each of the Standard dilutions to a suitable chromatographic plate
coated with a 0.25-mm layer of chromatographic silica gel. Place each spot over an opened bottle
of ammonium hydroxide for 20 seconds, then allow the plate to dry in a current of cold air for 20
seconds. Develop the chromatogram until the solvent front has moved about 17 cm. Remove the
plate from the developing chamber, allow the solvent to evaporate in a current of cold air for
approximately 2 minutes, and spray with a freshly prepared solution of 200 mg of p(dimethylamino)benzaldehyde in a mixture of 5.5 mL of hydrochloric acid and 4.5 mL of water. Dry
the plate at 60 for about 5 minutes and compare the chromatograms: the R value of the principal
F

spot obtained from the Test preparation corresponds to that obtained from the Standard
preparation, the sum of the intensities of any secondary spots in the chromatogram from the Test
preparation is not greater than the intensity of the principal spot from the 2.0% Standard dilution,
and the intensity of not more than one of the secondary spots is greater than that of the principal
spot from the 1.0% Standard dilution.
Assay Transfer about 200 mg of Ergotamine Tartrate, accurately weighed, to a small conical
flask, and dissolve in 15 mL of a mixture of 6 volumes of acetic anhydride and 100 volumes of
glacial acetic acid. Add 1 drop of crystal violet TS, and titrate with 0.05 N perchloric acid VS from a
10-mL buret. Perform a blank determination, and make any necessary correction. Each mL of 0.05
N perchloric acid is equivalent to 32.84 mg of (C33H35N5 O5)2 C4H6 O6.
Auxiliary Information Staff Liaison : Ravi Ravichandran, Ph.D., Senior Scientist
Expert Committee : (MDPP05) Monograph Development-Psychiatrics and Psychoactives
USP30NF25 Page 2053
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