510-22-5 Usage
Description
VOACANGINE is a bisindole alkaloid that exhibits ether-α-ago-gogo-related gene channel blocker activity in vitro, specifically acting as an hERG channel blocker. This alkaloid is widely found in various Stemmadenia species and Vocanga africana, V. dregii, and V. obtusa. It forms colorless needles when crystallized from MeOH and has a specific rotation of [α]D20 42° (c 1.0, CHCI3). VOACANGINE can be sublimed under vacuum at 135°C/0.01 mm and is readily soluble in CHCl3 or Me2CO, but only sparingly soluble in EtOH or MeOH. Hydrolysis with KOH followed by acidification with HCl yields Ibogaine.
Uses
Used in Pharmaceutical Industry:
VOACANGINE is used as a hERG channel blocker for its potential application in the development of drugs targeting the hERG channel, which is associated with various cardiac and non-cardiac diseases. Its ability to block the hERG channel makes it a valuable compound for research and drug development in this area.
Used in Research Applications:
VOACANGINE is used as a research tool for studying the function and role of the hERG channel in cellular processes. Its hERG channel blocking activity allows researchers to investigate the channel's involvement in various physiological and pathological conditions, contributing to a better understanding of the channel's role in health and disease.
Used in Drug Discovery and Development:
VOACANGINE is used as a lead compound in drug discovery and development, particularly for the development of new therapeutic agents targeting the hERG channel. Its unique chemical structure and biological activity make it a promising starting point for the design and synthesis of novel hERG channel modulators with potential therapeutic applications.
Used in Quality Control and Standardization:
VOACANGINE is used as a reference compound for quality control and standardization of natural products and extracts containing this alkaloid. Its well-defined chemical and physical properties make it an ideal candidate for ensuring the consistency, purity, and potency of such products in the pharmaceutical and nutraceutical industries.
References
lanot, Goutarel., Compt. rend., 241,986 (1955)
Stauffacher, Seebeck., Helv. Chim. Acta, 41,169 (1958)
Watts, Collera, Sandoval., Tetrahedron, 2, 173 (1958)
Schuler, Verbeck, Warren.,J. Chern. Soc., 4776 (1958)
Bartlett, Dickel, Taylor.,J. Amer. Chern. Soc., 80, 126 (1958)
Renner, Prins, Stoll., Helv. Chim. Acta, 42,1572 (1959)
Budzikiewicz etal., Bull. Soc. Chim. Fr., 1899 (1963)
Check Digit Verification of cas no
The CAS Registry Mumber 510-22-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 510-22:
(5*5)+(4*1)+(3*0)+(2*2)+(1*2)=35
35 % 10 = 5
So 510-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20-,22+/m0/s1
510-22-5Relevant articles and documents
Biosynthesis of an Anti-Addiction Agent from the Iboga Plant
Farrow, Scott C.,Kamileen, Mohamed O.,Caputi, Lorenzo,Bussey, Kate,Mundy, Julia E. A.,McAtee, Rory C.,Stephenson, Corey R. J.,O'Connor, Sarah E.
, p. 12979 - 12983 (2019/08/26)
(-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as treatments for opioid addiction. However, these compounds are produced by hard to source plants, making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (-)-voacangine, and de-esterified voacangine, which is converted to (-)-ibogaine by heating, enabling biocatalytic production of these compounds. Notably, (-)-ibogaine and (-)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Therefore, this discovery provides insight into enantioselective enzymatic formal Diels-Alder reactions.
