ChemicalBook--->CAS DataBase List--->8067-24-1

8067-24-1

8067-24-1 Structure

8067-24-1 Structure
IdentificationBack Directory
[Name]

Dihydroergotoxine mesylate
[CAS]

8067-24-1
[Synonyms]

Epos
Decril
cck179
Trigot
Perenan
Sponsin
Dulcion
Dacoren
Inorter
circanol
redergin
hydergin
Progeril
Ergoplus
Coristin
Novofluen
hydergine
ischelium
Ergodesit
Ergohydrin
Deapril ST
Co-dergocrine
Hydergine (8CI)
ergoloid mesylate
Codergine mesylate
ERGOLOID MESYLATES
Co-dercrine mesylate
ERGOLOIDMESYLATES,USP
co-dergocrinemesylate
DihydroergotoxinMesilat
dihydroergotoxinmesylate
Ergoloid mesylate salt
dihydroergotoxinemesilate
Codergocrine mesilate CRS
DIHYDROERGOTOXINE MESYLATE
Ergoloid Mesylates (300 mg)
Dihydroxy Ergotoxin mesylate
Codergocrine methanesulfonate
Dihydroergotoxine Mesilate RS
Dihydroergotoxin mesylate salt
dihydroergotoxinmethanesulfonate
dihydro-ergotoxinmethanesulfonate
dihydroergotoxinemethanesulfonate
dihydroergotoxinemethanesulphonate
Dihydroergotoxine mesylate 8067-24-1
DIHYDROERGOTOXINE MONOMETHANESULFONATE
dihydroergotoxine monomethanesulphonate
dihydroergotoxinemonomethanesulfonate(salt)
dihydro-ergotoxinmonomethanesulfonate(salt)
Ergoloid Mesylates (Dihydroergotoxine Mesilate)
Ergotoxine, dihydro-, monomethanesulfonate (salt)
Dihydro-ergotoxine Methanesulfonate (1.0mg/ml in DMSO)
[Molecular Formula]

C20H29N3O5S
[MDL Number]

MFCD00209881
[MOL File]

8067-24-1.mol
[Molecular Weight]

423.53
Chemical PropertiesBack Directory
[storage temp. ]

Store at RT
[solubility ]

DMSO: Slightly Soluble; Methanol: 1 mg/ml
[form ]

neat
[color ]

White to off-white
[InChIKey]

ONYMVHQTXOEAOV-TZWRWDCZNA-N
[SMILES]

C12C3=CC=CC=1[C@@]1([H])C[C@H](CN(C)[C@]1([H])CC2=CN3)C(=O)N[C@@H](C)CO.S(=O)(=O)(O)C |&1:6,9,13,22,r|
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

60
[Safety Statements ]

53-36/37/39-45
[RIDADR ]

1544
[RTECS ]

KE8800000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

3003490000
Hazard InformationBack Directory
[Description]

Ergoloid is a mixture of the ergot alkaloids dihydroergocornine, dihydroergocrystine, and dihydroergocryptine. It blocks reflex vasodilation and vasoconstriction induced by norepinephrine (Item No. 16673) in dogs when injected into the kidney at a dose of 0.15 mg. Ergoloid blocks norepinephrine-induced cAMP production in rat brain cortical homogenates ex vivo in a dose-dependent manner. It also acts as an erectogenic agent in rats. Formulations containing ergoloid have been used in the treatment of migraine headaches and vascular dementias.
[Uses]

Cognition adjuvant.
[Definition]

ChEBI: A mixture of hydrogenated ergot alkaloids consisting of the methanesulfonic acid salts of dihydroergocornine (R = CHMe2), dihydroergocristine (R = CH2Ph), and alpha- and beta-dihydroer ocryptine (R = CH2CHMe2 and CH(Me)Et, respectively). It is used for the symptomatic treatment of mild to moderate dementia in the elderly, although its value is not established.
[Brand name]

Alkergot (Sandoz); Circanol(3M Pharmaceuticals); Deapril (Bristol-Myers Squibb);Gerimal (Watson); Hydergine (Novartis).
[Biological Activity]

Dihydroergotoxine mesylate is a complex of closely related alkaloid salts. Binds with high affinity to the GABAA receptor Cl- channel, producing an allosteric interaction with the benzodiazepine site. Also interacts with central dopaminergic, serotonergic and adrenergic (α1) receptors. Displays antiproliferative activity in vitro (IC50 = 18 - 38 μM in prostate cancer cells) and exhibits cognition-enhancing, anticonvulsant and sedative activity in vivo. 
[Pharmacology]

The metabolic effects of ergoloid mesylates (Hydergine) may include enhancement of noradrenergic, dopaminergic and serotoninergic neurotransmission (Weil,1988) and reduction of free radicals. Schneider and Olin (1994) reviewed 151 reports on the use of Hydergine in senile dementia, but only 47 of these trials (31%) met strict criteria for meta-analysis. ACochrane review (Olin et al., 2001) confirmed that patients with VaD appeared to benefit more than patients with AD in terms of cognition,clinical global ratings and combined measures. However, compared with placebo, efficacy was very modest. Thus, there are no grounds to recommend its use.
[References]

[1] S MATSUSHITA. Pharmacological studies on reflex renal vasodilatation.[J]. Tohoku Journal of Experimental Medicine, 1969, 99 1: 51-57. DOI: 10.1620/tjem.99.51
[2] R. MARKSTEIN  H. W. The effect of dihydroergotoxin, phentolamine and pindolol on catecholamine-stimulated adenylcyclase in rat cerebral cortex[J]. FEBS Letters, 1975, 55 1: Pages 275-277. DOI: 10.1016/0014-5793(75)81010-6
[3] MILOVAN RADOSAVLJEVIC. Influence of Dihydroergotoxine, Bromocriptine, and Ergotamine on Penile Erection in Wistar Rats[J]. Journal of andrology, 2013, 33 5: 866-871. DOI: 10.2164/jandrol.111.015461
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