Tyramine | CAS#51-67-2

Tyramine
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 462783

CAS#: 51-67-2 (free base)

Description: Tyramine is an indirect sympathomimetic that occurs naturally in cheese and other foods. Tyramine does not directly activate adrenergic receptors, but it can serve as a substrate for adrenergic uptake systems and MONOAMINE OXIDASE to prolong the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals and may be a neurotransmitter in some invertebrate nervous systems.

Chemical Structure

Tyramine

CAS# 51-67-2 (free base)

Instruction

Theoretical Analysis

MedKoo Cat#: 462783
Name: Tyramine
CAS#: 51-67-2 (free base)
Chemical Formula: C8H11NO
Exact Mass: 137.08
Molecular Weight: 137.182
Elemental Analysis: Elemental Analysis: C, 70.04; H, 8.08; N, 10.21; O, 11.66

Price and Availability

Size	Price	Availability
10mg	USD -2	2 Weeks
200mg	USD -2	2 Weeks
500mg	USD -2	2 Weeks
1g	USD -2	2 Weeks
2g	USD -2	2 Weeks
5g	USD 210	2 Weeks
25g	USD 390	2 Weeks
50g	USD 630	2 Weeks
100g	USD 970	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 51-67-2 (free base) 60-19-5 (chloride)

Synonym: NSC 249188; NSC249188; NSC-249188; Uteramine; p-Tyramine;

IUPAC/Chemical Name: 4-(2-aminoethyl)phenol

InChi Key: DZGWFCGJZKJUFP-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2

SMILES Code: NCCc1ccc(O)cc1

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: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 137.18 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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Andersen G, Marcinek P, Sulzinger N, Schieberle P, Krautwurst D. Food sources and biomolecular targets of tyramine. Nutr Rev. 2019 Feb 1;77(2):107-115. doi: 10.1093/nutrit/nuy036. PMID: 30165672.

2: Gillman PK. A reassessment of the safety profile of monoamine oxidase inhibitors: elucidating tired old tyramine myths. J Neural Transm (Vienna). 2018 Nov;125(11):1707-1717. doi: 10.1007/s00702-018-1932-y. Epub 2018 Sep 25. PMID: 30255284.

3: Scheiner R, Reim T, Søvik E, Entler BV, Barron AB, Thamm M. Learning, gustatory responsiveness and tyramine differences across nurse and forager honeybees. J Exp Biol. 2017 Apr 15;220(Pt 8):1443-1450. doi: 10.1242/jeb.152496. Epub 2017 Feb 6. PMID: 28167800.

4: Bauknecht P, Jékely G. Ancient coexistence of norepinephrine, tyramine, and octopamine signaling in bilaterians. BMC Biol. 2017 Jan 30;15(1):6. doi: 10.1186/s12915-016-0341-7. PMID: 28137258; PMCID: PMC5282848.

5: Jiang W, Chen Y, He X, Hu S, Li S, Liu Y. A study of the tyramine/glucose Maillard reaction: Variables, characterization, cytotoxicity and preliminary application. Food Chem. 2018 Jan 15;239:377-384. doi: 10.1016/j.foodchem.2017.06.085. Epub 2017 Jun 20. PMID: 28873582.

6: Lange AB. Tyramine: from octopamine precursor to neuroactive chemical in insects. Gen Comp Endocrinol. 2009 May 15;162(1):18-26. doi: 10.1016/j.ygcen.2008.05.021. Epub 2008 Jun 8. PMID: 18588893.

7: Filer CN, Orphanos D. An efficient synthesis of trace amine-associated receptor agonist [1-14 C]tyramine. J Labelled Comp Radiopharm. 2019 Jan;62(1):24-27. doi: 10.1002/jlcr.3671. Epub 2018 Jul 31. PMID: 30007086.

8: Khan MZH, Liu X, Zhu J, Ma F, Hu W, Liu X. Electrochemical detection of tyramine with ITO/APTES/ErGO electrode and its application in real sample analysis. Biosens Bioelectron. 2018 Jun 15;108:76-81. doi: 10.1016/j.bios.2018.02.042. Epub 2018 Feb 23. PMID: 29501050.

9: Shulman KI, Walker SE. Refining the MAOI diet: tyramine content of pizzas and soy products. J Clin Psychiatry. 1999 Mar;60(3):191-3. PMID: 10192596.

10: Gillman K. "Much ado about nothing": monoamine oxidase inhibitors, drug interactions, and dietary tyramine. CNS Spectr. 2017 Oct;22(5):385-387. doi: 10.1017/S1092852916000651. Epub 2017 Feb 2. PMID: 28148312.

11: McCabe BJ. Dietary tyramine and other pressor amines in MAOI regimens: a review. J Am Diet Assoc. 1986 Aug;86(8):1059-64. PMID: 3525654.

12: Roeder T, Seifert M, Kähler C, Gewecke M. Tyramine and octopamine: antagonistic modulators of behavior and metabolism. Arch Insect Biochem Physiol. 2003 Sep;54(1):1-13. doi: 10.1002/arch.10102. PMID: 12942511.

13: Zhang D, Liu H, Geng W, Wang Y. A dual-function molecularly imprinted optopolymer based on quantum dots-grafted covalent-organic frameworks for the sensitive detection of tyramine in fermented meat products. Food Chem. 2019 Mar 30;277:639-645. doi: 10.1016/j.foodchem.2018.10.147. Epub 2018 Nov 2. PMID: 30502198.

14: Holland BW, Berry MD, Gray CG, Tomberli B. A Permeability Study of O2 and the Trace Amine p-Tyramine through Model Phosphatidylcholine Bilayers. PLoS One. 2015 Jun 18;10(6):e0122468. doi: 10.1371/journal.pone.0122468. PMID: 26086933; PMCID: PMC4472697.

15: Roeder T. Tyramine and octopamine: ruling behavior and metabolism. Annu Rev Entomol. 2005;50:447-77. doi: 10.1146/annurev.ento.50.071803.130404. PMID: 15355245.

16: Kochana J, Wapiennik K, Knihnicki P, Pollap A, Janus P, Oszajca M, Kuśtrowski P. Mesoporous carbon-containing voltammetric biosensor for determination of tyramine in food products. Anal Bioanal Chem. 2016 Jul;408(19):5199-210. doi: 10.1007/s00216-016-9612-y. Epub 2016 May 21. PMID: 27209590; PMCID: PMC4925687.

17: Zhang Y, Zhang M, Wei Q, Gao Y, Guo L, Al-Ghanim KA, Mahboob S, Zhang X. An Easily Fabricated Electrochemical Sensor Based on a Graphene-Modified Glassy Carbon Electrode for Determination of Octopamine and Tyramine. Sensors (Basel). 2016 Apr 13;16(4):535. doi: 10.3390/s16040535. PMID: 27089341; PMCID: PMC4851049.

18: Yılmaz C, Gökmen V. Formation of tyramine in yoghurt during fermentation - Interaction between yoghurt starter bacteria and Lactobacillus plantarum. Food Res Int. 2017 Jul;97:288-295. doi: 10.1016/j.foodres.2017.04.014. Epub 2017 Apr 22. PMID: 28578054.

19: Braunschweig AB, Elnathan R, Willner I. Monitoring the activity of tyrosinase on a tyramine/dopamine-functionalized surface by force microscopy. Nano Lett. 2007 Jul;7(7):2030-6. doi: 10.1021/nl0708819. Epub 2007 Jun 14. PMID: 17567175.

20: Kononenko NL, Wolfenberg H, Pflüger HJ. Tyramine as an independent transmitter and a precursor of octopamine in the locust central nervous system: an immunocytochemical study. J Comp Neurol. 2009 Feb 1;512(4):433-52. doi: 10.1002/cne.21911. PMID: 19025988.

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