Simmondsin

Chemical compound

none

Identifiers

IUPAC name

(2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2R,3R,4S,5S,6R)-3,4,

CAS Number

51771-52-9

PubChem CID

6437384

ChemSpider

4941947

UNII

O51H15R39K

Chemical and physical dataFormulaC₁₆H₂₅NO₉Molar mass375.374 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

N#C\C=C2/[C@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C[C@H](OC)[C@H](OC)[C@H]2O

InChI

InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10-,11+,12-,13+,14-,15+,16-/m1/s1
Key:KURSRHBVYUACKS-XGYNEUJOSA-N

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Simmondsin is a component of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis). While it had been considered toxic due to jojoba seed meal causing weight loss in animals, in recent years its appetite suppressant effect has also been researched as a potential treatment for obesity.^[1] It is thought to reduce appetite by increasing levels of cholecystokinin.^[2]^[3]^[4]^[5]

References

^ "Simmondsin From Jojoba - Checked for Appetite Suppression". United States Department of Agriculture, Agricultural Research Service.
^ Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M (December 1995). "Devazepide reverses the anorexic effect of simmondsin in the rat". The Journal of Endocrinology. 147 (3): 473–7. doi:10.1677/joe.0.1470473. PMID 8543917.
^ Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, et al. (August 1998). "Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats". Hormone and Metabolic Research. 30 (8): 504–8. doi:10.1055/s-2007-978921. PMID 9761380. S2CID 260166054.
^ Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M (April 2000). "The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat". Appetite. 34 (2): 147–51. doi:10.1006/appe.1999.0299. PMID 10744903. S2CID 42949049.
^ Boozer CN, Herron AJ (July 2006). "Simmondsin for weight loss in rats". International Journal of Obesity. 30 (7): 1143–8. doi:10.1038/sj.ijo.0803251. PMID 16462820. S2CID 1282460.

Antiobesity agents/Anorectics (A08)

Stimulants

Amphetamines and phenethylamines	4-Methylamphetamine^‡ Amfecloral Amfepentorex Amfepramone Amphetamine Amphetaminil Benzphetamine Cathine Cathinone Chlorphentermine Clobenzorex Cloforex Clortermine Dextroamphetamine Dimethylcathinone Ephedrine Ephedra^‡ Etilamfetamine Etolorex Fenethylline Fenproporex Fludorex Furfenorex^‡ Khat Lisdexamfetamine Mefenorex Methamphetamine Norfenfluramine Pentorex Phentermine (+topiramate) Xylopropamine Zylofuramine
Adrenergic agonists	Albuterol Clenbuterol^§ Ephedrine Ephedra^‡ Levopropylhexedrine Synephrine Terbutaline Yohimbine (Yohimbe)
Other	Aminorex^‡ Atomoxetine Benfluorex^‡ Bupropion (+naltrexone) Dexfenfluramine^‡ Dexmethylphenidate Difemetorex^‡ Fenbutrazate Fenfluramine (+phentermine^‡) Manifaxine Mazindol Methylphenidate Phendimetrazine Phenethylamine Phenmetrazine Phenylpropanolamine Pipradrol Propylhexedrine Pyrovalerone Sibutramine^‡ Tesofensine