Simmondsin

Simmondsin
Systematic (IUPAC) name

(2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2R,3R,4S,5S,6R)-3,4,
Identifiers
CAS Number	51771-52-9
ATC code	none
PubChem	CID 6437384
ChemSpider	4941947
Chemical data
Formula	C₁₆H₂₅NO₉
Molar mass	375.371 g/mol
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
(verify)

Simmondsin is an extract of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis), it was traditionally thought to be a toxic substance due to jojoba seed meal causing weight loss in animals, but in year 2000 been researched as a potential treatment for reducing appetite of obese individuals by helping to reduce craving for food.^[1] Several mechanisms of action are thought to be involved in the appetite suppressant effect.^[2]^[3]^[4]^[5]

References

↑ United States Department of Agriculture, Agricultural Research Service. Simmondsin From Jojoba - Checked for Appetite Suppression
↑ Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M. Devazepide reverses the anorexic effect of simmondsin in the rat. Journal of Endocrinology. 1995 Dec;147(3):473-7. PMID 8543917
↑ Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, Kühn E, Cokelaere M. Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats. Hormone and Metabolic Research. 1998 Aug;30(8):504-8. PMID 9761380
↑ Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M. The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat. Appetite. 2000 Apr;34(2):147-51. PMID 10744903
↑ Boozer CN, Herron AJ. Simmondsin for weight loss in rats. International Journal of Obesity (London). 2006 Jul;30(7):1143-8. PMID 16462820

Antiobesity agents/Anorectics (A08)

Central

Stimulants	4-Methylamphetamine^‡ Amfecloral Amfepentorex Amfepramone Aminorex^‡ Amphetamine Amphetaminil Atomoxetine Benfluorex^‡ Benzphetamine Bupropion (+naltrexone; +zonisamide^†) Cathine Cathinone Chlorphentermine Ciclazindol Clobenzorex Cloforex Clominorex Clortermine Dexfenfluramine^‡ Dextroamphetamine Dexmethylphenidate Difemetorex^‡ Dimethylcathinone Diphemethoxidine Ephedrine Ephedra^‡ Etilamfetamine Etolorex Fenbutrazate Fencamfamine Fenethylline Fenfluramine^‡ (+phentermine^‡) Fenproporex Fludorex Fluminorex Furfenorex^‡ Indanorex Khat Levopropylhexedrine Lisdexamfetamine Manifaxine Mazindol Mefenorex Methamphetamine Methylphenidate Norfenfluramine Pemoline Pentorex Phendimetrazine Phenethylamine Phenmetrazine Phentermine (+topiramate) Phenylpropanolamine Picilorex Pipradrol Prolintane Propylhexedrine Pseudoephedrine Pyrovalerone Radafaxine Reboxetine Setazindol Sibutramine^‡ Synephrine Tesofensine Viloxazine Xylopropamine Zylofuramine

Cannabinoid receptor antagonists	Drinabant^§ Ibipinabant^§ Otenabant^§ Rimonabant^‡ Rosonabant^§ Surinabant^§ Taranabant^§

Others	5-HTP Galactomannan Guar gum Glucomannan L-DOPA L-Phenylalanine L-Tryptophan L-Tyrosine Lorcaserin Lu AA-33810 Metformin Naltrexone Naloxone Oxyntomodulin P57 Peptide YY Topiramate Yohimbine (Yohimbe) Zonisamide water

Peripheral

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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