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

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
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
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
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.	2004 Nov	15470699
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
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.	2007	17465016
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
Liquid chromatography-tandem mass spectrometry characterization of ergocristam degradation products.	2008 Oct 1	18774762

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.

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

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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