ERGOCRISTINE

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 Search

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

Description
Sources: https://books.google.ru/books?id=MI544i8UdzUC&printsec=frontcover&hl=ru#v=onepage&q&f=false
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
dopamine secretion 11 Target ID: GO:0014046 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10438027	Releasing Agent 8
glutamate reuptake 1 Target ID: GO:0051935 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2809599	Inhibitor 8297
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2093864 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2822556	Agonist 2678
Adrenergic receptor alpha-1 169 Target ID: CHEMBL1907610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2822556	Antagonist 2778
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12235267 \| https://www.ncbi.nlm.nih.gov/pubmed/11961113	Inhibitor 8297	13.33 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay.	2001 May	11482600
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	11981648
Effects of topical natural ergot alkaloids on intraocular pressure and aqueous humor dynamics in ocular normotensive rabbits.	2002 Feb	11858614
Does decreased mowing frequency enhance alkaloid production in endophytic tall fescue and perennial ryegrass?	2002 May	12049232
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.	2004 Nov	15470699
Comparative studies on the effect of ergot contaminated feed on performance and health of piglets and chickens.	2005 Apr	16080303
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	16429824
The ergot alkaloid gene cluster in Claviceps purpurea: extension of the cluster sequence and intra species evolution.	2005 Jun	15904941
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	16278935
Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: Usefulness of precursor ion scan experiments.	2006	16941545
Quantitative determination of five ergot alkaloids in rye flour by liquid chromatography-electrospray ionisation tandem mass spectrometry.	2006 May 5	16519893
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.	2007	17465016
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	18030918
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	17505840
Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer.	2008 Dec	19330079
Claviceps nigricans and Claviceps grohii: their alkaloids and phylogenetic placement.	2008 Jun	18461998
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples.	2008 Nov-Dec	19202797
A basic tool for risk assessment: a new method for the analysis of ergot alkaloids in rye and selected rye products.	2009 Apr	19360756
Development and validation of an LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue.	2009 Aug 26	19642695
Ricinoleic acid as a marker for ergot impurities in rye and rye products.	2010 Apr 14	20297816
Contractile response of fescue-naive bovine lateral saphenous veins to increasing concentrations of tall fescue alkaloids.	2010 Jan	19783700
Cytotoxicity and accumulation of ergot alkaloids in human primary cells.	2011 Apr 11	21295106
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).	2013 Dec	24014644

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

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.

Name

Type

Language

ERGOCRISTINE

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