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Dihydroergotoxine mesylate

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Dihydroergotoxine mesylate Basic information

Product Name:
Dihydroergotoxine mesylate
Synonyms:
  • cck179
  • circanol
  • co-dergocrinemesylate
  • dihydroergotoxinemesilate
  • dihydroergotoxinemethanesulfonate
  • dihydroergotoxinemethanesulphonate
  • dihydroergotoxinemonomethanesulfonate(salt)
  • dihydroergotoxinmesylate
CAS:
8067-24-1
MF:
C20H29N3O5S
MW:
423.53
Mol File:
8067-24-1.mol
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Dihydroergotoxine mesylate Chemical Properties

storage temp. 
Store at RT
solubility 
DMSO: Slightly Soluble; Methanol: 1 mg/ml
form 
Solid
color 
White to off-white
InChI
InChI=1/C19H25N3O2.CH4O3S/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13;1-5(2,3)4/h3-5,8,11,13,15,17,20,23H,6-7,9-10H2,1-2H3,(H,21,24);1H3,(H,2,3,4)/t11-,13+,15+,17+;/s3
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|
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Safety Information

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
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Dihydroergotoxine mesylate Usage And Synthesis

Description

Ergoloid, also known as dihydroergotoxine mesylate, is a mixture of the ergot alkaloids dihydroergocornine, dihydroergocrystine, and dihydroergocryptine. It blocks reflex vasodilation and vasoconstriction induced by norepinephrine 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. Dihydroergotoxine mesylate binds with high affinity to GABAA receptor Cl- channel. Interacts with central dopaminergic, serotonergic and adrenergic (a1) receptors. Exhibits antirproliferative activity in vitro. Displays cognition-enhancing, anticonvulsant and sedative activity in vivo. Dihydroergotoxine mesylate is a substrate of GABA Receptor.

Definition

ChEBI: Dihydroergotoxine mesylate is 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.

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