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Details

Stereochemistry ACHIRAL
Molecular Formula C13H21NO2
Molecular Weight 223.3113
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TIGLOIDINE

SMILES

C\C=C(/C)C(=O)O[C@H]1C[C@@H]2CC[C@H](C1)N2C

InChI

InChIKey=UVHGSMZRSVGWDJ-WJKWMCMVSA-N
InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4+/t10-,11+,12-

HIDE SMILES / InChI

Molecular Formula C13H21NO2
Molecular Weight 223.3113
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Tigloidine is a tropane alkaloid and a naturally occurring analog of atropine, found in small quantities in Duboisia myoporoides. Tigloidine has been found to be beneficial in the treatment of Parkinsonism, Huntington’s Chorea and spastic paraplegia. Tigloidine may provide relief in parkinsonian patients by increasing the gamma-efferent activity and reducing alpha motoneurone activity. In preclinical models, Tigloidine failed to reverse sedation and ptosis in rats induced by reserpine and tetrabenazine. In mice, amphetamine response was not significantly affected by Tigloidine or atropine. However, in the cat and dog, it was markedly facilitated by Tigloidine but not by atropine.

Originator

Approval Year

PubMed

Substance Class Chemical
Record UNII
75GK1SV4EI
Record Status Validated (UNII)
Record Version