Dihydro Ergotamine Mesylate

Names

[ Name ]:
Dihydro Ergotamine Mesylate

[Synonym ]:
Methansulfonsäure--(6aR,9R,10aR)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]chinolin-9-carboxamid(1:1)
Ikaran
EINECS 228-235-6
dihydroergotamine methane sulfonate salt
Ergotaman, 9,10-dihydro-12'-hydroxy-2'-methyl-3',6',18-trioxo-5'-(phenylmethyl)-, (5'α,10α)-, methanesulfonate (1:1) (salt)
dihydroergotamine methanesulfonate
Dihydroergotamine mesylate,9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trionemesylate
Methansulfonsäure--(6aR,9R,10aR)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,
(6aR,9R,10aR)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-ca
dolo[4,3-fg]quinoléine-9-carboxamide (1:1)
Agit
Ergont
DET MS
MFCD00058615
(5'α,10α)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman methanesulfonate (salt)
(5'α,10α)-5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman methanesulfonate (1:1)
(6aR,9R,10aR)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide methanesulfonate (salt)
dhe45
rboxamide methanesulfonate (salt)
Diergo
acide méthanesulfonique - (6aR,9R,10aR)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-méthyl-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-méthyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoléine-9-carboxamide (1:1)
acide méthanesulfonique - (6aR,9R,10aR)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-méthyl-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-méthyl-4,6,6a,7,8,9,10,10a-octahydroin
Morena
Migranal

Biological Activity

[Description]:

Dihydroergotamine mesylate is an ergot alkaloid used to treat migraines.Target: 5-HT ReceptorsDihydroergotamine is not as effective as sumatriptan or phenothiazines as a single agent for treatment of acute migraine headache; however, when administered with an antiemetic, dihydroergotamine appears to be as effective as opiates, ketorolac, or valproate. Given its nonnarcotic properties, parenteral dihydroergotamine combined with an antiemetic should be considered as effective initial therapy in clinical practice [1]. The introduction of the intranasal formulation of DHE provides both pharmacologic and patient-convenience advantages for use in migraine therapy [2, 3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Neurological Disease

[References]

[1]. Colman, I., et al., Parenteral dihydroergotamine for acute migraine headache: a systematic review of the literature. Ann Emerg Med, 2005. 45(4): p. 393-401.

[2]. Saper, J.R., et al., DHE in the pharmacotherapy of migraine: potential for a larger role. Headache, 2006. 46 Suppl 4: p. S212-20.

[3]. Schaerlinger, B., et al., Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy. Br J Pharmacol, 2003. 140(2): p. 277-84.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
1001.8ºC at 760 mmHg

[ Melting Point ]:
232°C

[ Molecular Formula ]:
C₃₄H₄₁N₅O₈S

[ Molecular Weight ]:
679.783

[ Flash Point ]:
559.7ºC

[ Exact Mass ]:
679.267578

[ PSA ]:
180.96000

[ LogP ]:
2.87050

[ Index of Refraction ]:
-20 ° (C=0.25, JP Method)

[ Storage condition ]:
Store at RT

[ Water Solubility ]:
methanol: 21 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KE7920000

CHEMICAL NAME :: Ergotamine, 9,10-dihydro-, monomethanesulfonate (salt)

CAS REGISTRY NUMBER :: 6190-39-2

LAST UPDATED :: 199509

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C33-H37-N5-O5.C-H4-O3-S

MOLECULAR WEIGHT :: 679.86

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,468,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,468,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,328,1982

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
1544

[ WGK Germany ]:
3

[ RTECS ]:
KE7920000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Precursor & DownStream

Precursor

DownStream

Articles

Role of 5-HT1B/1Dreceptors in the reduction of formalin-induced nociception and secondary allodynia/hyperalgesia produced by antimigraine drugs in rats

Life Sci. 92(22) , 1046-54, (2013)

Aims The present study analyzed the potential antinociceptive effect of the antimigraine drugs sumatriptan, dihydroergotamine or methysergide in rats submitted to the formalin test. Moreover, by using...

Structural basis for molecular recognition at serotonin receptors.

Science 340(6132) , 610-4, (2013)

Serotonin or 5-hydroxytryptamine (5-HT) regulates a wide spectrum of human physiology through the 5-HT receptor family. We report the crystal structures of the human 5-HT1B G protein-coupled receptor ...

Intrapulmonary and intravenous administrations of dihydroergotamine mesylate have similar cardiovascular effects in the conscious dog.

Br. J. Pharmacol. 154(6) , 1254-65, (2008)

The effects of intrapulmonary artery (i.p.a.) administration of dihydroergotamine mesylate (DHE) were evaluated.Conscious beagle dogs (n=4) were given DHE via the i.p.a. or i.v. route as two 0.014 mg ...