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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H43N5O5
Molecular Weight 577.7143
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDRO-.ALPHA.-ERGOCRYPTINE

SMILES

CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)[C@@H]3C[C@H]4[C@@H](CC5=CNC6=C5C4=CC=C6)N(C)C3)(O[C@@]2(O)[C@@H]7CCCN7C1=O)C(C)C

InChI

InChIKey=PBUNVLRHZGSROC-VTIMJTGVSA-N
InChI=1S/C32H43N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1

HIDE SMILES / InChI

Description

Dihydro-alpha-ergocryptine is an ergot alkaloid that has an agonist activity on D2 dopaminergic receptors and a partial agonist activity on D1 receptors. It also demonstrated antagonistic activity towards alpha-adrenergic receptors. The drug was approved by FDA in combination with other alkaloids (dihydroergocornine, dihydroergocristine and dihydro-beta-ergocryptine mesylate salts) under the name Hydergine for the treatment of dimentia and cerebrovascular insufficiency.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Studies on the hypotensive action of dihydroergokryptine (DHK) and epinephrine-reversal in the dog and cat.
1957 Sep
Identification of alpha-adrenergic receptors in uterine smooth muscle membranes by [3H]dihydroergocryptine binding.
1976 Nov 25
New detection of brain dopamine receptors with (3H)dihydroergocryptine.
1977 Sep
Evidence for two alpha-adrenergic binding sites in liver plasma membranes. Studies with [3H]epinephrine and [3H]dihydroergocryptine.
1979 Jun 10
Binding of [3H]-dihydroergocryptine to alpha-adrenoceptors on intact human platelets [proceedings].
1979 May
Effects of trypsin on binding of [3H]epinephrine and [3H]-dihydroergocryptine to rat liver plasma membranes. Evidence for interconversion of binding sites.
1980 Jun 25
Binding of [3H]-prazosin and [3H]-dihydroergocryptine to rat cardiac alpha-adrenoceptors.
1981 May
The binding characteristics of [3H]-dihydroergocryptine on intact human platelets.
1982 May
Effect of 781094, a new selective alpha-adrenoceptor antagonist, on the aggregatory responses of human blood platelets and on binding of [3H]-dihydroergocryptine to these cells.
1983 Jun
Variations in circulating catecholamines fail to alter human platelet alpha-2-adrenergic receptor number or affinity for [3H]yohimbine or [3H]dihydroergocryptine.
1984 Sep
Preparation and characterization of conjugates of recombinant CD4 and deglycosylated ricin A chain using different cross-linkers.
1990 Jan-Feb

Sample Use Guides

In Vivo Use Guide
The recommended dosage (in form of hydergine tablets containing dihydroergocornine, dihydroergocristine, dihydro-alpha-ergocryptine and dihydro-beta-ergocryptine mesylate salts in an approximate weight ratio of 1:1:1) in the US is 1 mg three times daily. In Europe and Japan, up to 12 mg of hydergine daily have been used without serious adverse effects.
Route of Administration: Oral
In Vitro Use Guide
Primary cultures of rat cerebellar granule cells were exposed to toxic concentrations (100 uM) of glutamate in Mg2+-free buffer. Repeated addition of dihydro-alpha-ergocryptine (100 nM-1 uM, once a day from the second day in culture, last addition 3 hr before the glutamate pulse) protected cerebellar granule cells against the toxic action of glutamate.
Name Type Language
DIHYDRO-.ALPHA.-ERGOCRYPTINE
Common Name English
12'-HYDROXY-2'-(1-METHYLETHYL)-5'.ALPHA.-(2-METHYLPROPYL)-9,10.ALPHA.-DIHYDROERGOTAMAN-3',6',18-TRIONE
Common Name English
ERGOTAMAN-3',6',18-TRIONE, 9,10-DIHYDRO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)-, (5'.ALPHA.,10.ALPHA.)-
Common Name English
9,10-DIHYDROERGOCRYPTINE
Common Name English
DIHYDRO-ALPHA-ERGOCRYPTINE
Common Name English
Code System Code Type Description
EPA CompTox
25447-66-9
Created by admin on Tue Mar 06 12:25:43 UTC 2018 , Edited by admin on Tue Mar 06 12:25:43 UTC 2018
PRIMARY
CAS
25447-66-9
Created by admin on Tue Mar 06 12:25:43 UTC 2018 , Edited by admin on Tue Mar 06 12:25:43 UTC 2018
PRIMARY
NCI_THESAURUS
C75932
Created by admin on Tue Mar 06 12:25:43 UTC 2018 , Edited by admin on Tue Mar 06 12:25:43 UTC 2018
PRIMARY
ECHA (EC/EINECS)
246-993-6
Created by admin on Tue Mar 06 12:25:43 UTC 2018 , Edited by admin on Tue Mar 06 12:25:43 UTC 2018
PRIMARY
PUBCHEM
114948
Created by admin on Tue Mar 06 12:25:43 UTC 2018 , Edited by admin on Tue Mar 06 12:25:43 UTC 2018
PRIMARY SWITZERF
RXCUI
91170
Created by admin on Tue Mar 06 12:25:43 UTC 2018 , Edited by admin on Tue Mar 06 12:25:43 UTC 2018
PRIMARY RxNorm