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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

CC(C)[C@@]5(NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)O[C@@]6(O)[C@@H]7CCCN7C(=O)[C@H](CC8=CC=CC=C8)N6C5=O

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
4002
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
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Releasing Agent
8
Inhibitor
8504
Agonist
2752
Antagonist
2849
Inhibitor
8504
 13.33 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013-12
Cytotoxicity and accumulation of ergot alkaloids in human primary cells.
2011-04-11
Ricinoleic acid as a marker for ergot impurities in rye and rye products.
2010-04-14
Contractile response of fescue-naive bovine lateral saphenous veins to increasing concentrations of tall fescue alkaloids.
2010-01
Development and validation of an LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue.
2009-08-26
A basic tool for risk assessment: a new method for the analysis of ergot alkaloids in rye and selected rye products.
2009-04
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples.
2009-02-11
Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer.
2008-12
Liquid chromatography-tandem mass spectrometry characterization of ergocristam degradation products.
2008-10-01
Claviceps nigricans and Claviceps grohii: their alkaloids and phylogenetic placement.
2008-06
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS.
2008-05
LC-MS/MS multi-method for mycotoxins after single extraction, with validation data for peanut, pistachio, wheat, maize, cornflakes, raisins and figs.
2008-04
Ergot alkaloids in rye flour determined by solid-phase cation-exchange and high-pressure liquid chromatography with fluorescence detection.
2008-03
Effects of different levels of ergot in concentrates on the growing and slaughtering performance of bulls and on carry-over into edible tissue.
2007-10
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.
2007-10
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.
2007
Quantitative determination of five ergot alkaloids in rye flour by liquid chromatography-electrospray ionisation tandem mass spectrometry.
2006-05-05
Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: Usefulness of precursor ion scan experiments.
2006
The influence of ergot-contaminated feed on growth and slaughtering performance, nutrient digestibility and carry over of ergot alkaloids in growing-finishing pigs.
2005-12
Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds.
2005-11
The ergot alkaloid gene cluster in Claviceps purpurea: extension of the cluster sequence and intra species evolution.
2005-06
Comparative studies on the effect of ergot contaminated feed on performance and health of piglets and chickens.
2005-04
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.
2004-11
Does decreased mowing frequency enhance alkaloid production in endophytic tall fescue and perennial ryegrass?
2002-05
The effect of topical natural ergot alkaloids on the intraocular pressure and aqueous humor dynamics in rabbits with alpha-chymotrypsin-induced ocular hypertension.
2002-04
Effects of topical natural ergot alkaloids on intraocular pressure and aqueous humor dynamics in ocular normotensive rabbits.
2002-02
Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay.
2001-05
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 Mon Mar 31 23:05:08 GMT 2025
Edited
by admin
on Mon Mar 31 23:05:08 GMT 2025
Record UNII
3E58HO2T0U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERGOCRISTINE
MI   WHO-DD  
Common Name English
NSC-93743
Preferred 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
ERGOCRISTINE [MI]
Common Name English
Classification Tree Code System Code
DEA NO. 8612
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
Code System Code Type Description
PUBCHEM
31116
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
NSC
93743
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
MERCK INDEX
m4976
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY Merck Index
SMS_ID
100000128588
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
EVMPD
SUB35832
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-120-7
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
WIKIPEDIA
Ergocristine
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
FDA UNII
3E58HO2T0U
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID40891858
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
CAS
511-08-0
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
PRIMARY
CHEBI
4821
Created by admin on Mon Mar 31 23:05:08 GMT 2025 , Edited by admin on Mon Mar 31 23:05:08 GMT 2025
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
NIH
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