ChemicalBook CAS DataBase List 8067-24-1

8067-24-1

Name	Dihydroergotoxine mesylate
CAS	8067-24-1
Molecular Formula	C20H29N3O5S
MDL Number	MFCD00209881
Molecular Weight	423.53
MOL File	8067-24-1.mol

Chemical Properties

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 Data

Hazard Codes	T
Risk Statements	60 less more
Safety Statements	53-36/37/39-45 less more
RIDADR	1544
RTECS	KE8800000
HazardClass	6.1(b)
PackingGroup	III
HS Code	3003490000

Hazard Information

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.

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