Ergotamine

Title: Ergotamine
CAS Registry Number: 113-15-5
CAS Name: (5¢a)-12¢-Hydroxy-2¢-methyl-(phenylmethyl)ergotaman-3¢,6¢,18-trione
Molecular Formula: C33H35N5O5
Molecular Weight: 581.66
Percent Composition: C 68.14%, H 6.07%, N 12.04%, O 13.75%
Literature References: Vasoconstrictor found in ergot of Central Europe. Extraction procedure: Stoll, Helv. Chim. Acta 28, 1283 (1945). Pharmacology: E. Rothlin, Schweiz. Med. Wochenschr. 76, 1254 (1946). Structure: Stoll et al., ibid. 34, 1544 (1951). Total synthesis: Hofmann et al., Experientia 17, 206 (1961). Stereochemistry: Hofmann et al., ibid. 46, 2306 (1963). Comprehensive description: B. Kreilgard, Anal. Profiles Drug Subs. 6, 113-159 (1977). LC determn in tablets: U. R. Cieri, J. Assoc. Off. Anal. Chem. 70, 538 (1987); GC/MS determn in plasma: N. Feng et al., J. Chromatogr. 575, 289 (1992). Bioavailablity and efficacy in migraine: V. Ala-Hurula, Headache 22, 167 (1982). Review of clinical pharmacokinetics and treatment of headache: V. L. Perrin, Clin. Pharmacokinet. 10, 334-352 (1985). Review of teratogenic risk: G. V. Raymond, Teratology 51, 344-347 (1995).
Properties: Elongated prisms from benzene. Very hygroscopic. Darkens and dec on exposure to air, heat and light. Dec 212-214°. [a]D20 -160° (chloroform). Sol in about 70 parts methanol, 150 parts acetone, 300 parts alcohol; freely sol in chloroform, pyridine, glacial acetic acid; moderately sol in ethyl acetate; slightly in benzene. Almost insol in water, petr ether. LD50 in mice, rats, rabbits (mg/kg): 62, 80, 3 i.v.; in cats: 11 s.c. (Rothlin).
Optical Rotation: [a]D20 -160° (chloroform)
Toxicity data: LD50 in mice, rats, rabbits (mg/kg): 62, 80, 3 i.v.; in cats: 11 s.c. (Rothlin)
Derivative Type: Hydrochloride
Molecular Formula: C33H35N5O5.HCl
Molecular Weight: 618.12
Percent Composition: C 64.12%, H 5.87%, N 11.33%, O 12.94%, Cl 5.74%
Properties: Rectangular plates from 90% alc, mp 212° (dec). Sol in water-alcohol mixtures; sparingly in water or alcohol.
Melting point: mp 212° (dec)
Derivative Type: Tartrate
CAS Registry Number: 379-79-3
Trademarks: Ergomar (Lotus); Ergostat (Warner-Lambert); Gynergen (Novartis); Lingraine (Sanofi-Synthelabo)
Molecular Formula: (C33H35N5O5)2.C4H6O6
Molecular Weight: 1313.41
Percent Composition: C 64.01%, H 5.83%, N 10.66%, O 19.49%
Properties: Solvated crystals, e.g. the dimethanolate, heavy rhombic plates from methanol, mp 203° (dec). [a]D25 -125 to -155° (c = 0.4 in chloroform). One gram dissolves in 500 ml water or 500 ml alc. Protect from light and heat.
Melting point: mp 203° (dec)
Optical Rotation: [a]D25 -125 to -155° (c = 0.4 in chloroform)
Therap-Cat: Antimigraine.
Therap-Cat-Vet: Tartrate has been used as an oxytocic.
Keywords: Antimigraine; Serotonin Receptor Agonist.
Ergotaminine Ergothioneine Ergotinine Eriochrome?Black T Eriodictyol

Ergotamine
Ergotamine-skeletal.svg
Ergotamine ball-and-stick.png
Systematic (IUPAC) name
(6aR,9R)-N-((2R,5S,10aS,10bS)- 5-benzyl-10b-hydroxy-2-methyl- 3,6-dioxooctahydro-2H-oxazolo[3,2-a] pyrrolo[2,1-c]pyrazin-2-yl) -7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg] quinoline-9-carboxamide
Clinical data
Trade names Cafergot, Ergomar
AHFS/Drugs.com monograph
Pregnancy cat. X (US)
Legal status Prescription Only (S4) (AU) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability Intravenous: 100%,[1]
Intramuscular: 47%,[2]
Oral: <1% [3] (Enhanced by co-administration of caffeine [1])
Metabolism Hepatic [2]
Half-life 2 hours [2]
Excretion 90% biliary [2]
Identifiers
CAS number 113-15-5 YesY
ATC code N02CA02
PubChem CID 8223
IUPHAR ligand 149
DrugBank DB00696
ChemSpider 7930 YesY
UNII PR834Q503T YesY
KEGG D07906 YesY
ChEBI CHEBI:64318 N
ChEMBL CHEMBL442 YesY
Chemical data
Formula C33H35N5O5 
Mol. mass 581.66 g/mol
 N (what is this?)  (verify)

Ergotamine is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor.

It is used medicinally for treatment of acute migraine attacks (sometimes in combination with caffeine). Medicinal usage of ergot fungus began in the 16th century to induce childbirth, yet dosage uncertainties discouraged the use. It has been used to prevent post-partum haemorrhage (bleeding after childbirth). It was first isolated from the ergot fungus by Arthur Stoll at Sandoz in 1918 and marketed as Gynergen in 1921.[4]