Synephrine (R-isomer)
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MedKoo CAT#: 597940

CAS#: 614-35-7 (R-isomer)

Description: Synephrine (R-isomer), also known as (-)-Synephrine, inhibits eotaxin-1 expression via the STAT6 signaling pathway.


Chemical Structure

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Synephrine (R-isomer)
CAS# 614-35-7 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 597940
Name: Synephrine (R-isomer)
CAS#: 614-35-7 (R-isomer)
Chemical Formula: C9H13NO2
Exact Mass: 167.0946
Molecular Weight: 167.2
Elemental Analysis: C, 64.65; H, 7.84; N, 8.38; O, 19.14

Price and Availability

Size Price Availability Quantity
1.0g USD 365.0 2 Weeks
2.0g USD 550.0 2 Weeks
5.0g USD 950.0 2 Weeks
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Related CAS #: 5985-28-4 (HCl)   16589-24-5 (tartrate)   94-07-5 (racemate)   614-35-7 (R-isomer)    

Synonym: (-)-Synephrine; l-Sympatol; Oxedrine ((-)-);

IUPAC/Chemical Name: (R)-(-)-1-(4-Hydroxyphenyl)-2-(methylamino)ethanol

InChi Key: YRCWQPVGYLYSOX-VIFPVBQESA-N

InChi Code: InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1

SMILES Code: CNC[C@H](O)C1=CC=C(O)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 167.2 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Roh KB, Kim IH, Kim YS, Lee M, Lee JA, Jung E, Park D. Synephrine inhibits eotaxin-1 expression via the STAT6 signaling pathway. Molecules. 2014 Aug 8;19(8):11883-95. doi: 10.3390/molecules190811883. PubMed PMID: 25111027.

2: Wu Q, Li R, Soromou LW, Chen N, Yuan X, Sun G, Li B, Feng H. p-Synephrine suppresses lipopolysaccharide-induced acute lung injury by inhibition of the NF-κB signaling pathway. Inflamm Res. 2014 Jun;63(6):429-39. doi: 10.1007/s00011-014-0715-7. Epub 2014 Feb 1. PubMed PMID: 24487736.

3: Zheng X, Guo L, Wang D, Deng X. p-Synephrine: a novel agonist for neuromedin U2 receptor. Biol Pharm Bull. 2014;37(5):764-70. Epub 2014 Mar 4. PubMed PMID: 24598981.

4: Medana C, Calza P, Giancotti V, Dal Bello F, Aragno M, Baiocchi C. Study of the photocatalytic transformation of synephrine: a biogenic amine relevant in anti-doping analysis. Anal Bioanal Chem. 2013 Jan;405(2-3):1105-13. doi: 10.1007/s00216-012-6593-3. Epub 2012 Dec 4. PubMed PMID: 23208289.

5: Stohs SJ, Preuss HG, Shara M. A review of the human clinical studies involving Citrus aurantium (bitter orange) extract and its primary protoalkaloid p-synephrine. Int J Med Sci. 2012;9(7):527-38. Epub 2012 Aug 29. Review. PubMed PMID: 22991491; PubMed Central PMCID: PMC3444973.

6: Cui Z, Lee Y, Lee Y, Park D. p-Synephrine suppresses glucose production but not lipid accumulation in H4IIE liver cells. J Med Food. 2015 Jan;18(1):76-82. doi: 10.1089/jmf.2013.3133. PubMed PMID: 25379695; PubMed Central PMCID: PMC4281838.

7: de Oliveira AL, Comar JF, de Sá-Nakanishi AB, Peralta RM, Bracht A. The action of p-synephrine on hepatic carbohydrate metabolism and respiration occurs via both Ca(2+)-mobilization and cAMP production. Mol Cell Biochem. 2014 Mar;388(1-2):135-47. doi: 10.1007/s11010-013-1905-2. Epub 2013 Nov 28. PubMed PMID: 24287564.

8: Rossato LG, Costa VM, Limberger RP, Bastos Mde L, Remião F. Synephrine: from trace concentrations to massive consumption in weight-loss. Food Chem Toxicol. 2011 Jan;49(1):8-16. doi: 10.1016/j.fct.2010.11.007. Epub 2010 Nov 12. Review. PubMed PMID: 21075161.

9: Ratamess NA, Bush JA, Kang J, Kraemer WJ, Stohs SJ, Nocera VG, Leise MD, Diamond KB, Faigenbaum AD. The effects of supplementation with P-Synephrine alone and in combination with caffeine on resistance exercise performance. J Int Soc Sports Nutr. 2015 Sep 17;12:35. doi: 10.1186/s12970-015-0096-5. eCollection 2015. PubMed PMID: 26388707; PubMed Central PMCID: PMC4573476.

10: Shawky E. Determination of synephrine and octopamine in bitter orange peel by HPTLC with densitometry. J Chromatogr Sci. 2014 Sep;52(8):899-904. doi: 10.1093/chromsci/bmt113. Epub 2013 Aug 2. PubMed PMID: 23912767.

11: Stohs SJ, Preuss HG, Shara M. A review of the receptor-binding properties of p-synephrine as related to its pharmacological effects. Oxid Med Cell Longev. 2011;2011:482973. doi: 10.1155/2011/482973. Epub 2011 Aug 1. Review. PubMed PMID: 21904645; PubMed Central PMCID: PMC3166186.

12: Hong NY, Cui ZG, Kang HK, Lee DH, Lee YK, Park DB. p-Synephrine stimulates glucose consumption via AMPK in L6 skeletal muscle cells. Biochem Biophys Res Commun. 2012 Feb 24;418(4):720-4. doi: 10.1016/j.bbrc.2012.01.085. Epub 2012 Jan 28. PubMed PMID: 22306011.

13: Stohs SJ. Unsupported conclusions in the article "Synephrine-containing dietary supplement precipitating apical ballooning syndrome in a young female". Korean J Intern Med. 2014 May;29(3):388-92. doi: 10.3904/kjim.2014.29.3.388. Epub 2014 Apr 29. PubMed PMID: 24851076; PubMed Central PMCID: PMC4028531.

14: Fan JP, Zhang L, Zhang XH, Huang JZ, Tong S, Kong T, Tian ZY, Zhu JH. Molecularly imprinted polymers for selective extraction of synephrine from Aurantii Fructus Immaturus. Anal Bioanal Chem. 2012 Jan;402(3):1337-46. doi: 10.1007/s00216-011-5506-1. Epub 2011 Nov 16. PubMed PMID: 22086397.

15: Stohs SJ, Preuss HG, Keith SC, Keith PL, Miller H, Kaats GR. Effects of p-synephrine alone and in combination with selected bioflavonoids on resting metabolism, blood pressure, heart rate and self-reported mood changes. Int J Med Sci. 2011 Apr 28;8(4):295-301. PubMed PMID: 21537493; PubMed Central PMCID: PMC3085176.

16: Yi YN, Cheng XM, Liu LA, Hu GY, Wang ZT, Deng YD, Huang KL, Cai GX, Wang CH. Simultaneous determination of synephrine, arecoline, and norisoboldine in Chinese patent medicine Si-Mo-Tang oral liquid preparation by strong cation exchange high performance liquid chromatography. Pharm Biol. 2012 Jul;50(7):832-8. doi: 10.3109/13880209.2011.637505. Epub 2012 Apr 3. PubMed PMID: 22468825.

17: Stohs SJ, Preuss HG, Shara M. The safety of Citrus aurantium (bitter orange) and its primary protoalkaloid p-synephrine. Phytother Res. 2011 Oct;25(10):1421-8. doi: 10.1002/ptr.3490. Epub 2011 Apr 8. Review. PubMed PMID: 21480414.

18: Peixoto JS, Comar JF, Moreira CT, Soares AA, de Oliveira AL, Bracht A, Peralta RM. Effects of Citrus aurantium (bitter orange) fruit extracts and p-synephrine on metabolic fluxes in the rat liver. Molecules. 2012 May 16;17(5):5854-69. doi: 10.3390/molecules17055854. PubMed PMID: 22592089.

19: Gutiérrez-Hellín J, Salinero JJ, Abían-Vicen J, Areces F, Lara B, Gallo C, Puente C, Del Coso J. Acute consumption of p-synephrine does not enhance performance in sprint athletes. Appl Physiol Nutr Metab. 2016 Jan;41(1):63-9. doi: 10.1139/apnm-2015-0299. Epub 2015 Oct 6. PubMed PMID: 26673246.

20: Cabezas C, Simão A, Bermúdez C, Varela M, Peña I, Mata S, Fausto R, Alonso JL. Conformational analysis of octopamine and synephrine in the gas phase. J Phys Chem A. 2013 Jun 13;117(23):4907-15. doi: 10.1021/jp4032223. Epub 2013 May 30. PubMed PMID: 23675821.