U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H39N5O5
Molecular Weight 609.7147
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERGOCRISTINE

SMILES

[H][C@@]12CCCN1C(=O)[C@H](CC3=CC=CC=C3)N4C(=O)[C@](NC(=O)[C@H]5CN(C)[C@]6([H])CC7=CNC8=CC=CC(=C78)C6=C5)(O[C@@]24O)C(C)C

InChI

InChIKey=HEFIYUQVAZFDEE-MKTPKCENSA-N
InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28+,29+,34-,35+/m1/s1

HIDE SMILES / InChI

Molecular Formula C35H39N5O5
Molecular Weight 609.7147
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.deadiversion.usdoj.gov/fed_regs/rules/2011/fr0331.htm | https://www.ncbi.nlm.nih.gov/pubmed/2822556 | https://www.ncbi.nlm.nih.gov/pubmed/10438027 | https://www.ncbi.nlm.nih.gov/pubmed/2809599

Ergocristine is an alkoloid originally isolated from Iberian ergot. In the rat, ergocristine acts as an alpha 2-adrenoceptors agonist, and an alpha 1-adrenoceptors antagonist. It is able to regulate glutamate uptake and dopamine release. Ergocristine is controlled as a list I chemical of because it is considered as a chemical precursor used in the illicit manufacture of lysergic acid diethylamide,

CNS Activity

Curator's Comment: Ergocristine induces rotational behaviour in rats. No human data available.

Originator

Sources: Stoll, Burckhardt, Z. Physiol. Chem. 250, 1 (1937)
Curator's Comment: Ergocristine was isolated from ergot. https://books.google.ru/books?id=MI544i8UdzUC&printsec=frontcover&hl=ru#v=onepage&q&f=false | http://www.drugfuture.com/chemdata/ergocristine.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.
2004 Nov
The ergot alkaloid gene cluster in Claviceps purpurea: extension of the cluster sequence and intra species evolution.
2005 Jun
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.
2007
Effects of different levels of ergot in concentrates on the growing and slaughtering performance of bulls and on carry-over into edible tissue.
2007 Oct
A comparative study of topical natural ergot alkaloids on the intraocular pressure and aqueous humor dynamics in oclular normotensive and alpha-chymotrypsin-induced ocular hypertensive rabbits.
2007 Oct
LC-MS/MS multi-method for mycotoxins after single extraction, with validation data for peanut, pistachio, wheat, maize, cornflakes, raisins and figs.
2008 Apr
Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer.
2008 Dec
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS.
2008 May
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples.
2008 Nov-Dec
A basic tool for risk assessment: a new method for the analysis of ergot alkaloids in rye and selected rye products.
2009 Apr
Development and validation of an LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue.
2009 Aug 26
Ricinoleic acid as a marker for ergot impurities in rye and rye products.
2010 Apr 14
Contractile response of fescue-naive bovine lateral saphenous veins to increasing concentrations of tall fescue alkaloids.
2010 Jan
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Patents

Patents

Sample Use Guides

In Vivo Use Guide
The elevated prolactin concentration in rats declined immediately after a single bolus injection of ergocristine (30 ug/kg).
Route of Administration: Parenteral
Ergocristine concentrations starting at 5 uM are cytotoxic for porcine brain capillary endothelial cells . ergocristine was the most cytotoxic compound inducing apoptosis in human kidney cells starting at a concentration of 1uM in renal proximal tubule epithelial cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:09:20 GMT 2023
Edited
by admin
on Sat Dec 16 10:09:20 GMT 2023
Record UNII
3E58HO2T0U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERGOCRISTINE
MI   WHO-DD  
Common Name English
ERGOTAMAN-3',6',18-TRIONE, 12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(PHENYLMETHYL)-, (5'.ALPHA.)-
Common Name English
(6AR,9R)-N-((2R,5S,10AS,10BS)-5-BENZYL-10B-HYDROXY-3,6-DIOXO-2-(PROPAN-2-YL)OCTAHYDRO-8H-(1,3)OXAZOLO(3,2-A)PYRROLO(2,1-C)PYRAZIN-2-YL)-7-METHYL-4,6,6A,7,8,9-HEXAHYDROINDOLO(4,3-FG)QUINOLINE-9-CARBOXAMIDE
Systematic Name English
ERGOTAMINE TARTRATE IMPURITY D [EP IMPURITY]
Common Name English
Ergocristine [WHO-DD]
Common Name English
NSC-93743
Code English
ERGOCRISTINE [MI]
Common Name English
Classification Tree Code System Code
DEA NO. 8612
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
Code System Code Type Description
PUBCHEM
31116
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
NSC
93743
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
MERCK INDEX
m4976
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY Merck Index
SMS_ID
100000128588
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
EVMPD
SUB35832
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-120-7
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
WIKIPEDIA
Ergocristine
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
FDA UNII
3E58HO2T0U
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID40891858
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
CAS
511-08-0
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
CHEBI
4821
Created by admin on Sat Dec 16 10:09:20 GMT 2023 , Edited by admin on Sat Dec 16 10:09:20 GMT 2023
PRIMARY
Related Record Type Details
PARENT->PRECURSOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY