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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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
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/s1InChIKey
XCGSFFUVFURLIX-VFGNJEKYSA-NSmiles
CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4cccc2c34)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.