Synephrine (racemate)
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MedKoo CAT#: 592594

CAS#: 94-07-5 (racemate)

Description: Synephrine (racemate), also known as Synephrine (+/-), Oxedrine is a sympathetic alpha-adrenergic agonist with actions like PHENYLEPHRINE. It is used as a vasoconstrictor in circulatory failure, asthma, nasal congestion, and glaucoma.


Chemical Structure

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Synephrine (racemate)
CAS# 94-07-5 (racemate)

Theoretical Analysis

MedKoo Cat#: 592594
Name: Synephrine (racemate)
CAS#: 94-07-5 (racemate)
Chemical Formula: C9H13NO2
Exact Mass: 167.0946
Molecular Weight: 167.21
Elemental Analysis: C, 64.65; H, 7.84; N, 8.38; O, 19.14

Price and Availability

Size Price Availability Quantity
2.0g USD 250.0 2 Weeks
5.0g USD 450.0 2 Weeks
10.0g USD 650.0 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: Oxedrine; Synephrine (racemate); Synephrine (+/-); (+/-)-Synephrine;

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

InChi Key: YRCWQPVGYLYSOX-UHFFFAOYSA-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

SMILES Code: CNCC(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 167.21 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: 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.

2: Hofstetter R, Kreuder J, von Bernuth G. [The effect of oxedrine on the left ventricle and peripheral vascular resistance]. Arzneimittelforschung. 1985;35(12):1844-6. German. PubMed PMID: 4096743.

3: 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.

4: Kim NH, Pham NB, Quinn RJ, Shim JS, Cho H, Cho SM, Park SW, Kim JH, Seok SH, Oh JW, Kwon HJ. The Small Molecule R-(-)-β-O-Methylsynephrine Binds to Nucleoporin 153 kDa and Inhibits Angiogenesis. Int J Biol Sci. 2015 Jul 16;11(9):1088-99. doi: 10.7150/ijbs.10603. eCollection 2015. PubMed PMID: 26221075; PubMed Central PMCID: PMC4515819.

5: Stohs SJ, Badmaev V. A Review of Natural Stimulant and Non-stimulant Thermogenic Agents. Phytother Res. 2016 May;30(5):732-40. doi: 10.1002/ptr.5583. Epub 2016 Feb 9. Review. PubMed PMID: 26856274; PubMed Central PMCID: PMC5067548.

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: 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.

8: Spilstead KB, Learey JJ, Doeven EH, Barbante GJ, Mohr S, Barnett NW, Terry JM, Hall RM, Francis PS. 3D-printed and CNC milled flow-cells for chemiluminescence detection. Talanta. 2014 Aug;126:110-5. doi: 10.1016/j.talanta.2014.03.047. Epub 2014 Mar 26. PubMed PMID: 24881540.

9: 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.

10: 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.

11: Shara M, Stohs SJ, Mukattash TL. Cardiovascular Safety of Oral p-Synephrine (Bitter Orange) in Healthy Subjects: A Randomized Placebo-Controlled Cross-over Clinical Trial. Phytother Res. 2016 May;30(5):842-7. doi: 10.1002/ptr.5590. Epub 2016 Mar 7. PubMed PMID: 26948284.

12: 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.

13: 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.

14: 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.

15: Lincová D, Cernohorský M, Cepelík J, Mühlbachová E, Wenke W. Action of certain catechol and oxedrine sympathomimetics on lipid mobilization in vitro. Eur J Pharmacol. 1967 Oct;2(1):53-8. PubMed PMID: 5585237.

16: Gutiérrez-Hellín J, Del Coso J. Acute p-synephrine ingestion increases fat oxidation rate during exercise. Br J Clin Pharmacol. 2016 Aug;82(2):362-8. doi: 10.1111/bcp.12952. Epub 2016 May 7. PubMed PMID: 27038225; PubMed Central PMCID: PMC4972152.

17: 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.

18: Ratamess NA, Bush JA, Kang J, Kraemer WJ, Stohs SJ, Nocera VG, Leise MD, Diamond KB, Campbell SC, Miller HB, Faigenbaum AD. The Effects of Supplementation with p-Synephrine Alone and in Combination with Caffeine on Metabolic, Lipolytic, and Cardiovascular Responses during Resistance Exercise. J Am Coll Nutr. 2016 Nov-Dec;35(8):657-669. Epub 2016 Aug 2. PubMed PMID: 27484437.

19: 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.

20: Luliński P, Sobiech M, Zołek T, Maciejewska D. A separation of tyramine on a 2-(4-methoxyphenyl)ethylamine imprinted polymer: an answer from theoretical and experimental studies. Talanta. 2014 Nov;129:155-64. doi: 10.1016/j.talanta.2014.05.029. Epub 2014 May 24. PubMed PMID: 25127579.