U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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 of ?-Ergocryptine

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
49.0 nM [Ki]
28.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

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
Record UNII
6WFB60157B
Record Status Validated (UNII)
Record Version