?-Ergocryptine

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H41N5O5
Molecular Weight	575.6984
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)[C@H]3CN(C)[C@@H]4CC5=CNC6=CC=CC(=C56)C4=C3)(O[C@@]2(O)[C@@H]7CCCN7C1=O)C(C)C

InChI

InChIKey=YDOTUXAWKBPQJW-NSLWYYNWSA-N

InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20-,24-,25+,26+,31-,32+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C32H41N5O5
Molecular Weight	575.6984
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7665369 | https://www.ncbi.nlm.nih.gov/pubmed/11981648 | http://drugcentral.org/drugcard/885

Alpha-ergocryptine is a component of the ergotoxine complex; it is the main ergot alkaloid of Japanese & South American wid grasses. Alpha-ergocryptine is an agonist at the D2 dopamine receptor. Alpha-ergocryptine effectively decreases intraocular pressure in the alpha-chymotrypsin-induced model of ocular hypertension.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
guanylate cyclase activity 1 Target ID: GO:0004383 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6116597	Activator 1447
Serotonin 6 (5-HT6) receptor 44 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9798944	Antagonist 2849	49.0 nM [Ki]
Dopamine D2 receptor 311 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7665369	Agonist 2752	28.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ocular hypertension 52 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17505840 https://www.ncbi.nlm.nih.gov/pubmed/11981648	Primary		Preclinical	Unknown Approved Use Unknown
Hyperprolactinemia 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6369001	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Production and characterization of antibodies against fumigaclavine A.	2009-10	23605095
Determination of plasma ziprasidone using liquid chromatography with fluorescence detection.	2004-01-25	14670738
Ergovaline binding and activation of D2 dopamine receptors in GH4ZR7 cells.	1995-05	7665369

Patents

Sample Use Guides

In Vivo Use Guide

Rats were fed 0, 4, 20, 100 or 500 mg ergocryptine/kg diet for 28-32 days (equal to 0, 0.36, 1.7, 8.9 and 60 mg ergocryptine/kg body weight/day for females and 0, 0.34, 1.4, 6.6 and 44 mg ergocryptine/kg body weight/day for males). It is concluded that in rats fed ergocryptine for 28 days the dose-effect curve is rather steep and that the NOAEL is 4 mg/kg diet.

Route of Administration: Oral

In Vitro Use Guide

Bovine vascular smooth muscle cells (VSMC) from the dorsal metatarsal artery were grown in vitro and exposed to five concentrations (10(-6), 10(-8), 10(-9), 10(-11) and 0 M) of alpha-ergocryptine for 48 h. alpha-Ergocryptine stimulated (P < .01) growth at 10(-6) M concentration in growing cultures and at 10(-8) and 10(-9) M concentrations in quiescent cultures.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:06:31 GMT 2025` Edited by `admin` on `Mon Mar 31 21:06:31 GMT 2025`
Record UNII	6WFB60157B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

?-Ergocryptine

Common Name

English

Ergotaman-3?,6?,18-trione, 12?-hydroxy-2?-(1-methylethyl)-5?-(2-methylpropyl)-, (5??)-

Preferred Name

English

ERGOCRYPTINE

Common Name

English

NSC-407319

Code

English

NSC-169479

Code

English

ERGOKRYPTINE

Common Name

English

(5??)-12?-Hydroxy-2?-(1-methylethyl)-5?-(2-methylpropyl)ergotaman-3?,6?,18-trione

Systematic Name

English

.ALPHA.-ERGOCRYPTINE [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m4977