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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

CNS Active
3913
Curator's Comment: Ergocristine induces rotational behaviour in rats. No human data available.

Originator

Stoll, A.|Burckhardt, E.
1
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Releasing Agent
8
Inhibitor
8297
Agonist
2678
Antagonist
2778
Inhibitor
8297
 13.33 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay.
2001 May
The effect of topical natural ergot alkaloids on the intraocular pressure and aqueous humor dynamics in rabbits with alpha-chymotrypsin-induced ocular hypertension.
2002 Apr
Effects of topical natural ergot alkaloids on intraocular pressure and aqueous humor dynamics in ocular normotensive rabbits.
2002 Feb
Does decreased mowing frequency enhance alkaloid production in endophytic tall fescue and perennial ryegrass?
2002 May
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.
2004 Nov
Comparative studies on the effect of ergot contaminated feed on performance and health of piglets and chickens.
2005 Apr
The influence of ergot-contaminated feed on growth and slaughtering performance, nutrient digestibility and carry over of ergot alkaloids in growing-finishing pigs.
2005 Dec
Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds.
2005 Nov
Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: Usefulness of precursor ion scan experiments.
2006
Quantitative determination of five ergot alkaloids in rye flour by liquid chromatography-electrospray ionisation tandem mass spectrometry.
2006 May 5
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
Claviceps nigricans and Claviceps grohii: their alkaloids and phylogenetic placement.
2008 Jun
Ergot alkaloids in rye flour determined by solid-phase cation-exchange and high-pressure liquid chromatography with fluorescence detection.
2008 Mar
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
Liquid chromatography-tandem mass spectrometry characterization of ergocristam degradation products.
2008 Oct 1
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
Cytotoxicity and accumulation of ergot alkaloids in human primary cells.
2011 Apr 11
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Patents

Patents

US3567583
1

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
In Vitro Use Guide
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
Structure of LYSERGIDE
PARENT->PRECURSOR
Structure of ERGOCRISTINE PHOSPHATE
SALT/SOLVATE -> PARENT
Structure of ERGOCRISTINE ESYLATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ERGOTAMINE TARTRATE
PARENT -> IMPURITY
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