Synephrine
From Wikipedia, the free encyclopedia
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Synephrine
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| Systematic (IUPAC) name | |
| 4-[1-hydroxy-2-(methylamino)ethyl]phenol | |
| Identifiers | |
| CAS number | |
| ATC code | C01 S01 |
| PubChem | |
| Chemical data | |
| Formula | C9H13NO2 |
| Mol. mass | 167.205 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Synephrine (or oxedrine) is a drug aimed at encouraging fat 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 concerns about potential problems with heart disease risk[1][citation needed]. 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.
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[edit] Claims
- Burns fat
- Increases energy levels
- Increases metabolism
- Promotes weight loss
[edit] Synephrine is not 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.
- Phenylephrine acts primarily on alpha1 adrenergic receptors, so it has mainly vasoconstricting actions.
- Synephrine's pharmacology has not been thoroughly studied. Some comparisons with octopamine have been performed.[2] There is some evidence that it may act at β3.[3]
[edit] 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 cardiac infarcts.
Synephrine can also cause arrhythmias [4]. It is similar to ephedrine [4] and can therefore show similar symptoms (see ephedrine adverse effect).
[edit] References
- ^ Jordan S, Murty M, Pilon K (October 2004). "Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions" ([dead link] – Scholar search). CMAJ 171 (8): 993–4. PMID 15497209. http://www.cmaj.ca/cgi/pmidlookup?view=long&pmid=15497209.
- ^ 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.
- ^ 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:. PMID 10344530. http://link.springer.de/link/service/journals/00210/bibs/9359004/93590310.htm.
- ^ a b Livsmedelsverket (Swedish FDA)
[edit] External links
- Ischemic Stroke Associated With Use of an Ephedra-Free Dietary Supplement Containing Synephrine (Mayo Clinic)
- Slim Pickings: Looking Beyond Ephedra (New York Times)
- SYNEPHRINE: Is Chih-shih (Zhishi) Toxic?
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