Synephrine

s002-209x103Catalog Number: S002
Chemical Name: (1-(4-Hydroxyphenyl)-2-methylaminoethanol 4-Hydroxy-α-(methylaminomethyl)benzyl alcohol
Botanical Source: Fruit of citrus aurantium
Molecular Formula: C9H13O2N
Molecular  Weight: 167.21
CAS Number: 94-07-5
Purity: 98% determined by HPLCs003-180x200
Appearance: Off white powder
Melting Temperature: 187 °C
Storage Temperature: 4 – 8 ºC
Solubility: 50mg/mL in 1M HCl
Price:

Catalog #
Size
Price (USD)
S002
5 g
28.50
S002
10 g
55.00
S002
50 g
190.50
S002
100 g
350.00

Pharmacological Actions: Synephrine is one of the three main substances extracted from the fruit of C. aurantium, bitter orange. It occurs naturally in the human body in small quantities and may act as a neurotransmitter (1). Since 1927, it has been used as a pharmaceutical (2), commonly in the form of eye drops under the name oxedrine.

Synephrine is an α-adrenergic agonist (3) that also has some β-adrenergic properties (4). Therefore it is expected to potentially increase energy expenditure and decrease food intake (5). It is well documented that synephrine alkaloids (SAs) reduce food intake in rodents (6), and several studies indicate that SAs can reduce body weight in rodents (6-8). SAs have been shown to promote lipolysis in adipocytes
through beta-adrenergic stimulation (9). These data suggest that SAs can selectively reduce body fat without compromising lean tissue.
Similarly, SAs are noted to increase lipoprotein lipase activity in the parametrial fat pad of female hamsters (10). Few clinical trials have examined the effects of SAs on body weight and/or body composition in human. In these short-term studies, body weight and/or fat loss appears to be enhanced by SAs (11)

   References:
1.        Kim KW, Kim HD, Jung JS, Woo RS, Kim HS, Suh HW, Kim YH, and Song DK (2001) Characterization of antidepressant-like effects of p-synephrine stereoisomers. Naunyn Schmiedebergs Arch Pharmacol 364, 21-26.

2.        Starke K (1998) A history of Naunyn-Schmiedeberg’s archives of pharmacology. Naunyn Schmiedebergs Arch Pharmacol 358, 1-109.

3.        Brown CM, McGrath JC, Midgley JM, Muir AG, O’Brien JW, Thonoor CM, Williams CM, and Wilson VG (1988) Activities of octopamine and synephrine stereoisomers on alpha-adrenoceptors. Br J Pharmacol 93, 417-429.

4.        Jordan R, Midgley JM, Thonoor CM, and Williams CM (1987) Beta-adrenergic activities of octopamine and synephrine stereoisomers on guinea-pig atria and trachea. J Pharm Pharmacol 1987; 39, 752-754.

5.        Astrup A (2000) Thermogenic Drugs as a Strategy for Treatment of Obesity . Endocrine 13, 207-212.

6.        Yeh SY (1999) Comparative anorectic effects of metaraminol and phenylephrine in rats. Physiol Behav 68, 227-234.

7.        National Toxicology Program. NTP toxicology and carcinogenesis studies of phenylephrine hydrochloride (CAS, No. 61-76-7) in F344/N rats and B6C3F1 mice (Feed Studies). Natl Toxicol Program Tech Rep Series 1987; 322: 1-172.

8.        Calapai G, Firenzuoli F, Saitta A, Squadrito F, Arlotta MR, Costantino G, and Inferrera G (1999) Antiobesity and cardiovascular toxic effects of Citrus aurantium extracts in the rat: a preliminary report. Fitoterapia 70, 586-592.

9.        Mooney RA and McDonald JM (1984) Effect of phenylephrine on lipolysis in rat adipocytes: no evidence for an alpha-adrenergic mechanism. Int J Biochem 16, 55-59.

10.        Desfaits AC, Lafond J, and Savard R (1995) The effects of a selective alpha-1 adrenergic blockade on the activity of adipose tissue lipoprotein lipase in female hamsters. Life Sci 57, 705-713.

11.        Haaz S, Fontaine KR, Cutter G, Limdi N, Perumean-Chaney S, and Allison DB (2006) Citrus aurantium and synephrine alkaloids in the treatment of overweight and obesity: an update. Obesity Reviews 7, 79-88.