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Substance Name: Dihydroergotamine [INN:BAN]
RN: 511-12-6
UNII: 436O5HM03C
InChIKey: LUZRJRNZXALNLM-JGRZULCMSA-N

Note

  • A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.

Molecular Formula

  • C33-H37-N5-O5

Molecular Weight

  • 583.685
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Dopamine Agents
  • Dopamine Agonists
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Sensory System Agents
  • Vasoconstrictor Agents

Names and Synonyms

Name of Substance

  • Dihydroergotamine
  • Dihydroergotamine [INN:BAN]

MeSH Heading

  • Dihydroergotamine

Synonyms

  • 9,10-Dihydroergotamine
  • BRN 5720196
  • Dehydroergotamine
  • DHE
  • Dihidroergotamina
  • Dihidroergotamina [INN-Spanish]
  • Dihydroergotamine
  • Dihydroergotaminum
  • Dihydroergotaminum [INN-Latin]
  • Diidroergotamina
  • Diidroergotamina [DCIT]
  • EINECS 208-123-3
  • Ergotamine, 9,10-dihydro-
  • Levadex
  • MAP 0004
  • MAP0004
  • UNII-436O5HM03C

Systematic Names

  • Dihydroergotamine
  • Ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha,10alpha)-

Registry Numbers

CAS Registry Number

  • 511-12-6

FDA UNII

  • 436O5HM03C

Other Registry Numbers

  • 11019-70-8
  • 1381-00-6
  • 17680-45-4
  • 26913-96-2
  • 29087-32-9
  • 409-63-2
  • 47842-41-1
  • 5965-22-0
  • 6016-53-1
  • 7762-45-0
  • 98302-70-6

Related Registry Number

  • 6190-39-2 (mesylate)

System Generated Number

  • 0000511126

Structure Descriptors

InChI

1S/C33H37N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1

InChIKey

LUZRJRNZXALNLM-JGRZULCMSA-N

Smiles

N12[C@@]([C@H]3N(CCC3)C([C@@H]1Cc1ccccc1)=O)(O[C@](NC([C@@H]1C[C@@H]3c4c5c(c[nH]c5ccc4)C[C@H]3[N@@](C1)C)=O)(C)C2=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous 68mg/kg (68mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 76, Pg. 1254, 1946.
mouse LD50 intravenous 118mg/kg (118mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 105, Pg. 317, 1956.
mouse LD50 oral > 8gm/kg (8000mg/kg)   French Medicament Patent Document. Vol. #2292M,
mouse LD50 subcutaneous 80mg/kg (80mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 53, 1968.
rabbit LD50 intravenous 25mg/kg (25mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 105, Pg. 317, 1956.
rabbit LD50 oral > 8gm/kg (8000mg/kg)   French Medicament Patent Document. Vol. #2292M,