510-22-5 Usage
Description
This alkaloid is of widespread occurrence, being found in Stemmadenia species
and also is Vocanga africana, v. dregii and V. obtusa. It forms colourless needles
when crystallized from MeOH and has [0'10 - 42° (c 1.0, CHCI3). It sublimes under vacuum at 135°CjO.01 mm and is readily soluble in CHC13 or Me2CO, but
only sparingly so in EtOH or MeOH. Hydrolysis with KOH followed by acidification
with HCl yields Ibogaine (q.v.).
Uses
(-)-Voacangine is a bisindole alkaloid with ether-?a-?go-?go-?related gene channel blocker activity in vitro. hERG channel blocker.
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.
