Ajmalan is a parent hydride used in the IUPAC nomenclature of natural products and also in CAS nomenclature.[1] It is a 20-carbon alkaloid with six rings and seven chiral centres.

Ajmalan

The conventional representation of the ajmalan skeleton, with numbering
Names
IUPAC name
(1S,9R,10S,12S,13S,16S,17S)-13-Ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C20H26N2/c1-3-12-11-22-17-8-13(12)14-9-20(10-18(14)22)15-6-4-5-7-16(15)21(2)19(17)20/h4-7,12-14,17-19H,3,8-11H2,1-2H3/t12-,13+,14+,17+,18+,19+,20+/m1/s1
    Key: AJONLKUQHMDAFG-UAWDQXROSA-N
  • CC[C@@H]1CN2[C@H]3C[C@@H]1[C@H]4[C@@H]2C[C@]5(C4)[C@H]3N(c6c5cccc6)C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The name is derived from ajmaline, an antiarrhythmic alkaloid isolated from the roots of Rauvolfia serpentina[2] which is formally a dihydroxy-derivative of ajmalan. The –an ending indicates that ajmalan is partially saturated. Ajmaline itself is named after Hakim Ajmal Khan, a distinguished practitioner of the Unani school of traditional medicine in South Asia.[3]

The absolute configuration of the seven chiral carbon atoms in ajmalan is defined by convention, as is the numbering system.[1] The stereochemistry is the same as that in naturally occurring ajmaline, and corresponds to (2R,3S,5S,7S,15S,16R,20S) using conventional numbering.

Ajmalan can be systematically named as

(1S,4S,5S,7S,8R,16S,17R)-4-ethyl-9-methyl-2,9-diazahexacyclo[14.2.1.02,7.05,18.08,16.010,15]nonadeca-10,12,14-triene

or as

(2S,3S,5S,6aS,11aR,11bS,12R)-4H,11H-3-ethyl-11-methyl-1,2,3,5,6,6a,11a,11b-octahydro-2,5,6a-(epiethane[1,1,2]triyl)indolo[2,3-c]quinolizine.

Note that the numbering of the atoms in the systematic names is different from the conventional numbering of ajmalan.[4]

The ajmalan skeleton is similar to those of certain other alkaloids, and ajmalan could also be given the following semisystematic names:

(2β,5β,16R,20β)-1-methyl-1,2,19,20-tetrahydro-5,16-cyclo-16a-homo-17-norakuammilan;
(2β,5β,7β,16R,20β)-1-methyl-2,7-dihydro-5,16:7,17-dicyclocorynan;
(2β,7β,16R,20β)-1-methyl-2,7,19,20-tetrahydro-7,17-cyclosarpagan;
(2β,3α,7β,20β)-1-methyl-2,7,19,20-tetrahydro-3,4:7,17-dicyclo-22-norvobasan;
(2β,5β,7β,16R,20β)-1-methyl-2,7-dihydro-5,16:7,17-dicyclo-17-secoyohimban.

However, the relative complexity even of these names justifies the use of ajmalan as a defined parent hydride in alkaloid nomenclature.

References

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  1. ^ a b "Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999)", Pure Appl. Chem., 71 (4): 587–643, doi:10.1351/pac199971040587.
  2. ^ Siddiqui, S.; Siddiqui, R. H. (1931). J. Indian Chem. Soc. 8: 667–80.
  3. ^ Ahmed Nasim Sandilvi (2003). "Salimuzzaman Siddiqui: pioneer of scientific research in Pakistan. Archived 2007-09-27 at the Wayback Machine" Daily Dawn, 2003-04-12. Retrieved on 2007-07-19.
  4. ^ The numbering is also different between the von Baeyer name and the fusion name, given the different conventions which apply to the two methods of nomenclature.