CAS 545-84-6

Ibogamine-18-carboxylic acid, 20-hydroxy-12-methoxy-, methyl ester, (20S)-

Description:

Ibogamine-18-carboxylic acid, 20-hydroxy-12-methoxy-, methyl ester, (20S)-, with CAS number 545-84-6, is a chemical compound derived from the iboga alkaloid family, which is primarily found in the Tabernanthe iboga plant. This compound exhibits a complex structure characterized by a bicyclic framework typical of indole alkaloids, featuring multiple functional groups, including a carboxylic acid and methoxy groups. It is known for its potential psychoactive properties and has been studied for its effects on the central nervous system. The (20S)- configuration indicates a specific stereochemistry that can influence its biological activity and interactions with receptors. Ibogamine derivatives are of interest in pharmacological research, particularly in the context of addiction treatment and neuroprotection. However, due to its psychoactive nature, the use and study of this compound are subject to regulatory scrutiny in many regions. Overall, ibogamine-18-carboxylic acid methyl ester represents a fascinating area of study within medicinal chemistry and pharmacology.

Formula: C₂₂H₂₈N₂O₄

InChI: InChI=1/C22H28N2O4/c1-12(25)16-8-13-10-22(21(26)28-3)19-15(6-7-24(11-13)20(16)22)17-9-14(27-2)4-5-18(17)23-19/h4-5,9,12-13,16,20,23,25H,6-8,10-11H2,1-3H3/t12-,13+,16+,20-,22+/m0/s1

InChI key: InChIKey=OYMQKBZMKFJPMH-VJMPXSKLSA-N

SMILES: C(OC)(=O)[C@]12C3=C(C=4C(N3)=CC=C(OC)C4)CC[N@@]5[C@]1([C@@]([C@H](C)O)(C[C@](C2)(C5)[H])[H])[H]

Synonyms:

• Ibogamine-18-carboxylic acid, 20-hydroxy-12-methoxy-, methyl ester, (20S)-
• Voacangarine
• (-)-Voacangarine
• 6,9-Methano-5H-pyrido[1′,2′:1,2]azepino[4,5-b]indole, ibogamine-18-carboxylic acid deriv.
• Voacristine
• (20S)-20-Hydroxy-12-methoxyibogamine-18-carboxylic acid methyl ester
• COACRISTINE

(−)-Voacangarine

CAS: 545-84-6

(–)-Voacangarine, an indole alkaloid isolated from V. africana, exhibits cytotoxicity towards various cell lines including HepG2, A375, MDA-MB-231, SH-SY5Y, and CT26 with IC50 values of 20 µg/ml. Additionally, it demonstrates cytostatic effects on wild-type S. cerevisiae and is cytotoxic to Δrad3-e5 and Δrad6-1 mutant strains of S. cerevisiae, which have defects in DNA strand break repair and the mutagenic repair pathway, respectively.

Formula: C₂₂H₂₈N₂O₄

Color and Shape: Solid

Molecular weight: 384.47

Ref: TM-TN7544

Voacristine

CAS: 545-84-6

Formula: C₂₂H₂₈N₂O₄

Molecular weight: 384.48

Ref: 4Z-V-111001

(−)-Voacangarine

CAS: 545-84-6

(−)-Voacangarine is an indole alkaloid, which is a secondary metabolite naturally occurring in certain plant species, particularly within the Apocynaceae family, such as Voacanga africana. This compound is biosynthesized through complex enzymatic pathways within the plant tissues, contributing to the plant's defensive mechanisms against herbivores and pathogens.

Formula: C₂₂H₂₈N₂O₄

Purity: Min. 95%

Molecular weight: 384.5 g/mol

Ref: 3D-AAA54584