Mesembrenone information

Mesembrenone
Names
	Preferred IUPAC name (3aR,7aS)-3a-(3,4-Dimethoxyphenyl)-1-methyl-1,2,3,3a,7,7a-hexahydro-6H-indol-6-one
Identifiers
CAS Number	468-54-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	187467 ;
PubChem CID	216272;
CompTox Dashboard (EPA)	DTXSID60963667 ;
	InChI InChI=1S/C17H21NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-7,10,16H,8-9,11H2,1-3H3/t16-,17-/m0/s1 Key: HDNHBCSWFYFPAN-IRXDYDNUSA-N;
	SMILES O=C3\C=C/[C@]2(c1ccc(OC)c(OC)c1)[C@@H](N(CC2)C)C3;
Properties
Chemical formula	C17H21NO3
Molar mass	287.359 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Mesembrenone is an alkaloid constituent of Sceletium tortuosum (Kanna) and minor constituent of Lampranthus aureus and Lampranthus spectabilis ^[1]

Similar to modern synthetic antidepressants, it is a potent (IC₅₀ < 1 μM) selective inhibitor of the serotonin transporter (SERT) (that is, a selective serotonin reuptake inhibitor; K_i = 27 nM) and also a phosphodiesterase 4 (PDE4) inhibitor (K_i = 470 nM).^[2]

^ Smith, Michael T.; Field, Courtney R.; Crouch, Neil R.; Hirst, Manton (1998). "The Distribution of Mesembrine Alkaloids in Selected Taxa of the Mesembryanthemaceae and their Modification in the Sceletium Derived 'Kougoed'". Pharmaceutical Biology. 36 (3): 173–179. doi:10.1076/phbi.36.3.173.6350.
^ Harvey, A. L.; Young, L. C.; Viljoen, A. M.; Gericke, N. P. (October 2011). "Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids". Journal of Ethnopharmacology. 137 (3): 1124–1129. doi:10.1016/j.jep.2011.07.035. PMID 21798331.

[1] Smith, Michael T.; Field, Courtney R.; Crouch, Neil R.; Hirst, Manton (1998). "The Distribution of Mesembrine Alkaloids in Selected Taxa of the Mesembryanthemaceae and their Modification in the Sceletium Derived 'Kougoed'". Pharmaceutical Biology. 36 (3): 173–179. doi:10.1076/phbi.36.3.173.6350.

[pmid21798331-2] Harvey, A. L.; Young, L. C.; Viljoen, A. M.; Gericke, N. P. (October 2011). "Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids". Journal of Ethnopharmacology. 137 (3): 1124–1129. doi:10.1016/j.jep.2011.07.035. PMID 21798331.

Mesembrenone information

and 28 Related for: Mesembrenone information

Mesembrenone

Lampranthus spectabilis

Lampranthus

Caffeine

Phosphodiesterase inhibitor

Serotonin reuptake inhibitor

Theophylline

Pentoxifylline

Tadalafil

Apremilast

Papaverine

Mesembryanthemum tortuosum

Pimobendan

Vardenafil

Icariin

Tofisopam

PDE5 inhibitor

Crisaborole

Doxofylline

Vinpocetine

Roflumilast

Avanafil

Sildenafil

Milrinone

Theobromine

Dipyridamole

PDE3 inhibitor

Udenafil