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Synephrine
Systematic (IUPAC) name
4-[1-hydroxy-2-(methylamino)ethyl]phenol
Identifiers
CAS number 94-07-5
ATC code C01CA08 S01GA06
PubChem 7172
Chemical data
Formula C9H13NO2 
Mol. mass 167.205 g/mol
Therapeutic considerations
Pregnancy cat.  ?
Legal status

Synephrine (or oxedrine) is a drug commonly used for weight loss. While its effectiveness is widely debated, synephrine has gained significant popularity as an alternative to ephedrine, a related substance which has been made illegal or restricted in many countries due to its use as a precursor in the illicit manufacturing of methamphetamine. Products containing bitter orange or synephrine are suspected of causing adverse cardiovascular reactions [1]. Synephrine is derived primarily from the fruit of Citrus aurantium, a relatively small citrus tree, of which several of its more common names include Bitter Orange, Sour Orange, and Zhi shi. Dietary supplements generally supply single oral doses of 3-30 mg, while as a pharmaceutical agent it is given orally or by parenteral injection in 20-100 mg doses as a vasoconstrictor to hypotensive patients.[2]

Contents

Claims

  • Burns fat
  • Increases energy
  • Increases metabolism
  • Promotes weight loss
  • Increases body heat

Synephrine and neosynephrine

There has been some confusion surrounding synephrine and phenylephrine (neosynephrine), one of its positional isomers. The chemicals are similar in structure; the only difference is the location of the aromatic hydroxyl group. In synephrine, the hydroxyl is at the para position, whereas in neosynephrine it is at the meta position. Each compound has differing biological properties.

Associated risks

Many diet products such as Stacker 2 contain synephrine along with caffeine. Some reports have indicated that such diet pills cause numerous harmful effects. The Mayo Clinic published a report that suggested a link between Stacker 2 pills and increased risk of ischemic stroke, increased blood pressure, and myocardial infarction.

Synephrine can also cause arrhythmias [5]. It is similar to ephedrine [5] and can therefore show similar symptoms (see ephedrine adverse effects).

References

  1. ^ Jordan S, Murty M, Pilon K (October 2004). "Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions". CMAJ : Canadian Medical Association Journal = Journal De l'Association Medicale Canadienne 171 (8): 993–4. PMID 15497209. 
  2. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1471-1472.
  3. ^ Brown CM, McGrath JC, Midgley JM, et al. (February 1988). "Activities of octopamine and synephrine stereoisomers on alpha-adrenoceptors". Br. J. Pharmacol. 93 (2): 417–29. PMID 2833972. 
  4. ^ Carpéné C, Galitzky J, Fontana E, Atgié C, Lafontan M, Berlan M (April 1999). "Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells". Naunyn Schmiedebergs Arch. Pharmacol. 359 (4): 310–21. doi:10.1007/PL00005357. PMID 10344530. http://link.springer.de/link/service/journals/00210/bibs/9359004/93590310.htm. 
  5. ^ a b Livsmedelsverket (Swedish FDA)

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