Ajmalan

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
CAS Number	34612-39-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37673;
ChemSpider	21429431;
PubChem CID	9548857;
	InChI 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;
	SMILES 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). Infobox references

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.

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[14.2.1.0^2,7.0^5,18.0^8,16.0^10,15]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

1 2 "Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999)". Pure and Applied Chemistry. 71 (4): 587–643. doi:10.1351/pac199971040587..
↑ Siddiqui, S.; Siddiqui, R. H. (1931). J. Indian Chem. Soc. 8: 667–80.
↑ 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.
↑ 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.

[IUPAC-1] 1 2 "Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999)". Pure and Applied Chemistry. 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.

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References