Ephedroxane

Ephedroxane
Clinical data
Drug class	putative anti-inflammatory drug; central nervous system depressant (sedative)
ATC code	none;
Identifiers
	IUPAC name (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one;
CAS Number	16251-46-0;
PubChem CID	161171;
ChemSpider	141584;
KEGG	C17902;
ChEBI	CHEBI:81372;
CompTox Dashboard (EPA)	DTXSID80167382;
Chemical and physical data
Formula	C11H13NO2
Molar mass	191.230 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]1[C@H](OC(=O)N1C)C2=CC=CC=C2;
	InChI InChI=1S/C11H13NO2/c1-8-10(14-11(13)12(8)2)9-6-4-3-5-7-9/h3-8,10H,1-2H3/t8-,10-/m0/s1; Key:MNYARIILPGRTQL-WPRPVWTQSA-N;

Ephedroxane (EX) It is a natural plant alkaloid belonging to a group of compounds related to aminorex, also known as phenyloxazolamines, found in plants of the genus Ephedra.^[1]^[2] Its structural skeleton consists of a 2-oxazolidinone with two methyl substituents at the nitrogen atom in the 3-position and at the carbon atom in the 4-position, as well as a phenyl group in the 5-position.

Natural occurrence

Ephedroxane has been found in plants of the genus Ephedra.^[1]^[2]^[3]

The compounds are diastereomers^{[clarification needed]} (also known as pseudoephedroxane) or structurally related to ephedroxane are termed ephedroxanes; they usually exert a depressant effect, in contrast to ephedrines (such as ephedrine or pseudoephedrine) on the central nervous system, which confirms their sedative effect; it is emphasised, however, that the effects of ephedroxane were generally more intense compared with its isomer pseudoephedroxane; ephedroxanes did not cause tissue contraction, but at the same time enhanced the action of norepinephrine in the catecholaminergic system.^[4]

Efedroxan inhibited carrageenan-induced hind-paw oedema in mice, as well as in mice that had undergone adrenalectomy. Oedema of the hind paw induced by histamine, serotonin, bradykinin and prostaglandin E1 was suppressed by efedroxane, indicating its anti-inflammatory activity^[2]^[3] in early exudative inflammation; however, this mechanism was not associated with the sympathetic nervous system. Furthermore, ephedroxane also inhibited the biosynthesis of prostaglandin E2.^[5]

1 2 Tang S, Ren J, Kong L, Yan G, Liu C, Han Y, et al. (January 2023). "Ephedrae Herba: A Review of Its Phytochemistry, Pharmacology, Clinical Application, and Alkaloid Toxicity". Molecules. 28 (2). Basel, Switzerland: 663. doi:10.3390/molecules28020663. PMC 9863261. PMID 36677722.
1 2 3 Wang Z, Zhang J, Zhan J, Gao H (November 2021). "Screening out anti-inflammatory or anti-viral targets in Xuanfei Baidu Tang through a new technique of reverse finding target". Bioorganic Chemistry. 116 105274. doi:10.1016/j.bioorg.2021.105274. PMC 8373853. PMID 34455301.
1 2 Jeppesen AS, Soelberg J, Jäger AK (October 2012). "Antibacterial and COX-1 Inhibitory Effect of Medicinal Plants from the Pamir Mountains, Afghanistan". Plants. 1 (2). Basel, Switzerland: 74–81. doi:10.3390/plants1020074. PMC 4844265. PMID 27137641.
↑ Hikino H, Ogata K, Kasahara Y, Konno C (May 1985). "Pharmacology of ephedroxanes". Journal of Ethnopharmacology. 13 (2): 175–191. doi:10.1016/0378-8741(85)90005-4. PMID 4021515.
↑ Kasahara Y, Hikino H, Tsurufuji S, Watanabe M, Ohuchi K (August 1985). "Antiinflammatory actions of ephedrines in acute inflammations1". Planta Medica. 51 (4): 325–331. doi:10.1055/s-2007-969503 (inactive 6 September 2026). PMID 17340525.{{cite journal}}: CS1 maint: DOI inactive as of September 2026 (link)