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Substance Name: Ergotamine [INN:BAN]
RN: 113-15-5
UNII: PR834Q503T
InChIKey: XCGSFFUVFURLIX-VFGNJEKYSA-N

Note

  • A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.

Molecular Formula

  • C33-H35-N5-O5

Molecular Weight

  • 581.669
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-1 Receptor Agonists
  • Adrenergic alpha-Agonists
  • Analgesics
  • Analgesics, Non-Narcotic
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Neurotransmitter Agents
  • Oxytocics
  • Peripheral Nervous System Agents
  • Reproductive Control Agents
  • Sensory System Agents
  • Serotonin Agents
  • Serotonin Receptor Agonists
  • Vasoconstrictor Agents

Names and Synonyms

Name of Substance

  • Ergotamine
  • Ergotamine [INN:BAN]

MeSH Heading

  • Ergotamine

Synonyms

  • 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
  • 4-25-00-00964 (Beilstein Handbook Reference)
  • BRN 0078890
  • EINECS 204-023-9
  • Ergonsvine
  • Ergostat
  • Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-
  • Ergotamin
  • Ergotamina
  • Ergotamina [INN-Spanish]
  • Ergotamine
  • Ergotaminine
  • Ergotaminum
  • Ergotaminum [INN-Latin]
  • Gynergen
  • HSDB 4076
  • NSC 95090
  • Tartrate
  • UNII-PR834Q503T

Systematic Names

  • Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)-
  • Ergotamine

Registry Numbers

CAS Registry Number

  • 113-15-5

FDA UNII

  • PR834Q503T

Other Registry Numbers

  • 1080650-16-3
  • 6915-20-4
  • 98260-30-1

Related Registry Number

  • 379-79-3 (2:1 tartrate salt)

System Generated Number

  • 0000113155

Structure Descriptors

InChI

1S/C33H35N5O5/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/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1

InChIKey

XCGSFFUVFURLIX-VFGNJEKYSA-N

Smiles

[nH]1c2c3c(c1)C[C@@H]1C(c3ccc2)=C[C@H](C[N@@]1C)C(=O)N[C@]1(C(N2[C@@]([C@H]3N(C([C@@H]2Cc2ccccc2)=O)CCC3)(O1)O)=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous 11mg/kg (11mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 76, Pg. 1254, 1946.
chicken LDLo intramuscular 2gm/kg (2000mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 119, Pg. 1302, 1935.
chicken LDLo intramuscular 2gm/kg (2000mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: ATAXIA		 Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 119, Pg. 1302, 1935.
chicken LDLo intravenous 2400ug/kg (2.4mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 179, Pg. 115, 1935.
frog LDLo subcutaneous 33mg/kg (33mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 27, Pg. 459, 1923.
human TDLo subcutaneous 171ug/kg/17D- (0.171mg/kg) SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES		 Muenchener Medicinische Wochenschrift. Vol. 80, Pg. 1784, 1933.
infant TDLo subcutaneous 4400ug/kg/4D- (4.4mg/kg) VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION Klinische Wochenscrift. Vol. 9, Pg. 258, 1930.
man TDLo intravenous 3570ng/kg (0.00357mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 107, 1938.
mouse LD50 intravenous 52mg/kg (52mg/kg) BEHAVIORAL: ATAXIA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 285, 1948.
mouse LDLo unreported 50mg/kg (50mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 103, 1938.
rabbit LD50 intravenous 3mg/kg (3mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 76, Pg. 1254, 1946.
rat LD50 intravenous 80mg/kg (80mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 76, Pg. 1254, 1946.
rat LDLo subcutaneous 100mg/kg (100mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 119, Pg. 1302, 1935.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 213.5 dec deg C   EXP
log P (octanol-water) 2.530 (none)   EST
Atmospheric OH Rate Constant 4.54E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.