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Substance Name: Prajmalium bitartrate [INN:BAN]
RN: 2589-47-1
UNII: H671L9190Z
InChIKey: VZAUGYDMVQSQAO-VOTNWUEESA-M

Note

  • A derivative of the rauwolfia alkaloid AJMALINE. It is an anti-arrhythmia agent, but may cause liver damage.

Molecular Formulas

  • C23-H32-N2-O2.C4-H6-O6
  • C23-H33-N2-O2.C4-H5-O6
  • C27-H38-N2-O8

Molecular Weight

  • 518.6032
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Prajmalium bitartrate [INN:BAN]

Synonyms

  • 17R,21-alpha-Dihydroxy-4-propylajmalanium hydrogen tartrate
  • Bitartrate de prajmalium
  • Bitartrate de prajmalium [INN-French]
  • Bitartrato de prajmalio
  • Bitartrato de prajmalio [INN-Spanish]
  • EINECS 219-975-0
  • GT-1012
  • N(sup 4)-Propylajmalinium hydrogen tartrate
  • N-Propylajmaline bitartrate
  • N-Propylajmaline hydrogen tartrate
  • N-Propylajmalinium bitartrate
  • N-Propylajmalinium hydrogen tartrate
  • N-Propylajmaliniumhydrogentartrat
  • N-Propylajmaliniumhydrogentartrat [German]
  • Neo-gilurytmal
  • NPAP
  • Prajmalii bitartras
  • Prajmalii bitartras [INN-Latin]
  • Prajmaline bitartrate
  • Prajmaline hydrogen tartrate
  • Prajmalio bitartrato
  • Prajmalio bitartrato [DCIT]
  • Prajmalium bitartrate
  • Prajmalium bitatrate
  • UNII-H671L9190Z

Systematic Names

  • Ajmalanium, 17,21-dihydroxy-4-propyl-, (17R,21alpha)-, salt with (2R,3R)-2,3-dihydroxybutanedioic acid (1:1)
  • Ajmalanium, 17R,21-alpha-dihydroxy-4-propyl-, hydrogen tartrate
  • N-Propylajmalinium tartrate
  • Prajmalium bitartrate

Registry Numbers

CAS Registry Number

  • 2589-47-1

FDA UNII

  • H671L9190Z

System Generated Number

  • 0002589471

Molecular Formulas

Molecular Formulas

  • C23-H32-N2-O2.C4-H6-O6
  • C23-H33-N2-O2.C4-H5-O6
  • C27-H38-N2-O8

Molecular Formula Fragments

  • C23-H32-N2-O2
  • C23-H33-N2-O2
  • C4-H5-O6
  • C4-H6-O6
  • COMPONENT

Structure Descriptors

InChI

1S/C23H33N2O2.C4H6O6/c1-4-10-25-17-11-14(13(5-2)22(25)27)19-18(25)12-23(21(19)26)15-8-6-7-9-16(15)24(3)20(17)23;5-1(3(7)8)2(6)4(9)10/h6-9,13-14,17-22,26-27H,4-5,10-12H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/q+1;/p-1/t13-,14-,17-,18-,19-,20-,21+,22+,23+,25-;1-,2-/m01/s1

InChIKey

VZAUGYDMVQSQAO-VOTNWUEESA-M

Smiles

CCC[N@@+]12[C@H]3C[C@@H]([C@@H]([C@H]1O)CC)[C@H]4[C@@H]2C[C@@]5([C@H]3N(c6c5cccc6)C)[C@@H]4O.[C@@H]([C@H](C(=O)[O-])O)(C(=O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intravenous 330ug/kg (0.33mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 2085, 1972.
man TDLo oral 1400ug/kg (1.4mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" British Medical Journal. Vol. 2, Pg. 675, 1977.
man TDLo oral 22857ug/kg/20 (22.857mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LIVER: "JAUNDICE, CHOLESTATIC"

BLOOD: EOSINOPHILIA
Postgraduate Medical Journal. Vol. 56, Pg. 738, 1980.
mouse LD50 intraperitoneal 21265ug/kg (21.265mg/kg)   United States Patent Document. Vol. #4552877,
mouse LD50 intravenous 1700ug/kg (1.7mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 2085, 1972.
mouse LD50 oral 33714ug/kg (33.714mg/kg)   United States Patent Document. Vol. #4552877,
rat LD50 intravenous 3400ug/kg (3.4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 2085, 1972.
rat LD50 oral 54mg/kg (54mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 2085, 1972.
women LDLo oral 22mg/kg (22mg/kg)   Archives of Toxicology. Vol. 37, Pg. 135, 1977.