Conolidine

Not to be confused with clonidine.
Conolidine
Names
Systematic IUPAC name
(4E,5S)-4-Ethylidene-1,4,5,7-tetrahydro-2,5-ethanoazocino[4,3-b]inden-6(3H)-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C17H18N2O/c1-2-11-9-19-8-7-12(11)17(20)16-14(10-19)13-5-3-4-6-15(13)18-16/h2-6,12,18H,7-10H2,1H3/b11-2-/t12-/m0/s1 ☒N
    Key: DBGBUYFOJXOYNY-RENATIMJSA-N ☒N
  • InChI=1/C17H18N2O/c1-2-11-9-19-8-7-12(11)17(20)16-14(10-19)13-5-3-4-6-15(13)18-16/h2-6,12,18H,7-10H2,1H3/b11-2-/t12-/m0/s1
    Key: DBGBUYFOJXOYNY-RENATIMJBD
  • CC(=O)NC(=NCCC[C@H]1C(=O)N2CCC[C@@H]2C(=O)N[C@H]3C[C@H](N(C3=O)[C@H](C(=O)N[C@H](C(=O)N1)CCCC(=O)O)CC4=CN=CN4)O)N
Properties
C17H18N2O
Molar mass 266.344 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tabernaemontana divaricata

Conolidine is an indole alkaloid. Preliminary reports suggest that it could provide analgesic effects with few of the detrimental side-effects associated with opioids such as morphine, though at present it has only been evaluated in mouse models.

Conolidine was first isolated in 2004 from the bark of the Tabernaemontana divaricata (crape jasmine) shrub which is used in traditional Chinese medicine.[1]

The first asymmetric total synthesis of conolidine was developed by Micalizio and coworkers in 2011.[2] This synthetic route allows access to either enantiomer (mirror image) of conolidine via an early enzymatic resolution. Notably, evaluation of the synthetic material resulted in the discovery that both enantiomers of the synthetic compound show analgesic effects.[3]

  1. ^ Kam, T.-S., Pang, H. S., Choo, Y. M., Komiyama, K. (Apr 2004). "Biologically Active Ibogan and Vallesamine Derivatives from Tabernaemontana divaricata". Chemistry & Biodiversity. 1 (4): 646–656. doi:10.1002/cbdv.200490056. PMID 17191876. S2CID 12805328.
  2. ^ Tarselli, M. A., Raehal, K. M., Brasher, A. K., Groer, C., Cameron, M. D., Bohn, L. M., Micalizio, G. C. (2011). "Synthesis of Conolidine, a Potent Non-Opioid Analgesic for Tonic and Persistent Pain". Nature Chemistry. 3 (6): 449–453. Bibcode:2011NatCh...3..449T. doi:10.1038/nchem.1050. PMID 21602859.
  3. ^ Ball, P. (May 2011). "Compound Offers Pain Relief Without the Complications". Nature. doi:10.1038/news.2011.313.