Synonym
Epinephrine bitartrate; l-Adrenaline bitartrate; Bronitin; Epinephrine acid tartrate; Adrenaline acid tartrate; Adrenaline bitartrate; (−)-Epinephrine (+)-bitartrate salt; L-Adrenaline (+)-bitartrate salt; L-Adrenaline D-hydrogentartrate; L-Epinephrine D-hydrogentartrate;
IUPAC/Chemical Name
(R)-4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol (2R,3R)-2,3-dihydroxysuccinate
InChi Key
YLXIPWWIOISBDD-NDAAPVSOSA-N
InChi Code
InChI=1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1
SMILES Code
O[C@@H](C(O)=O)[C@H](C(O)=O)O.CNC[C@@H](C1=CC=C(C(O)=C1)O)O
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
>2 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
Biological target:
Epinephrine bitartrate (Adrenalinium) is an alpha- and beta-adrenergic receptor stimulator.
In vitro activity:
Epinephrine (dissolved in ascorbic acid 0.5M) reduced in a dose and time-dependent manner the activity of the Na+/K+ ATPase in Caco-2 cells. The highest inhibitory effect was observed at 20 min and at a dose of 0.5 mM. Accordingly in all other experiments cell were treated with epinephrine for 20min and at a concentration of 0.5mM. Ascorbic acid alone exerted no significant effect on the activity of the pump (Fig 1).
Reference: PLoS One. 2018; 13(2): e0193139. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5821373/
In vivo activity:
Epinephrine injected after the pre-exposure training modulated the latent memory in a dose- and time-dependent manner: 0.01 mg/kg given shortly after the short pre-exposure enhanced the memory, but 0.5 mg/kg given shortly after the long pre-exposure impaired it. Epinephrine (0.01 mg/kg) also made the latent memory lasting longer as the rats treated with it showed significant avoidance behavior when they had the shock training at 12 or 21 days after the pre-exposure.
Reference: Neurobiol Learn Mem. 2021 Jul;182:107447. https://pubmed.ncbi.nlm.nih.gov/33915301/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
67.0 |
201.03 |
| Water |
67.0 |
201.03 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
333.29
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:
1. El Moussawi L, Chakkour M, Kreydiyyeh SI. Epinephrine modulates Na+/K+ ATPase activity in Caco-2 cells via Src, p38MAPK, ERK and PGE2. PLoS One. 2018 Feb 21;13(2):e0193139. doi: 10.1371/journal.pone.0193139. PMID: 29466417; PMCID: PMC5821373.
2. Al-Sawalha N, Pokkunuri I, Omoluabi O, Kim H, Thanawala VJ, Hernandez A, Bond RA, Knoll BJ. Epinephrine Activation of the β2-Adrenoceptor Is Required for IL-13-Induced Mucin Production in Human Bronchial Epithelial Cells. PLoS One. 2015 Jul 10;10(7):e0132559. doi: 10.1371/journal.pone.0132559. PMID: 26161982; PMCID: PMC4498766.
3. Liang KC, Chen DY. Epinephrine modulates memory of latent learning in an inhibitory avoidance task. Neurobiol Learn Mem. 2021 Jul;182:107447. doi: 10.1016/j.nlm.2021.107447. Epub 2021 Apr 26. PMID: 33915301.
4. Martinho R, Oliveira A, Correia G, Marques M, Seixas R, Serrão P, Moreira-Rodrigues M. Epinephrine May Contribute to the Persistence of Traumatic Memories in a Post-traumatic Stress Disorder Animal Model. Front Mol Neurosci. 2020 Oct 26;13:588802. doi: 10.3389/fnmol.2020.588802. PMID: 33192300; PMCID: PMC7649334.
In vitro protocol:
1. El Moussawi L, Chakkour M, Kreydiyyeh SI. Epinephrine modulates Na+/K+ ATPase activity in Caco-2 cells via Src, p38MAPK, ERK and PGE2. PLoS One. 2018 Feb 21;13(2):e0193139. doi: 10.1371/journal.pone.0193139. PMID: 29466417; PMCID: PMC5821373.
2. Al-Sawalha N, Pokkunuri I, Omoluabi O, Kim H, Thanawala VJ, Hernandez A, Bond RA, Knoll BJ. Epinephrine Activation of the β2-Adrenoceptor Is Required for IL-13-Induced Mucin Production in Human Bronchial Epithelial Cells. PLoS One. 2015 Jul 10;10(7):e0132559. doi: 10.1371/journal.pone.0132559. PMID: 26161982; PMCID: PMC4498766.
In vivo protocol:
1. Liang KC, Chen DY. Epinephrine modulates memory of latent learning in an inhibitory avoidance task. Neurobiol Learn Mem. 2021 Jul;182:107447. doi: 10.1016/j.nlm.2021.107447. Epub 2021 Apr 26. PMID: 33915301.
2. Martinho R, Oliveira A, Correia G, Marques M, Seixas R, Serrão P, Moreira-Rodrigues M. Epinephrine May Contribute to the Persistence of Traumatic Memories in a Post-traumatic Stress Disorder Animal Model. Front Mol Neurosci. 2020 Oct 26;13:588802. doi: 10.3389/fnmol.2020.588802. PMID: 33192300; PMCID: PMC7649334.
1: Zhang Q, Liu B, Zhao L, Qi Z, Shao H, An L, Li C. Efficacy of vasopressin-epinephrine compared to epinephrine alone for out of hospital cardiac arrest patients: A systematic review and meta-analysis. Am J Emerg Med. 2017 Oct;35(10):1555-1560. doi: 10.1016/j.ajem.2017.07.040. Epub 2017 Jul 18. Review. PubMed PMID: 28754320.
2: Chime NO, Riese VG, Scherzer DJ, Perretta JS, McNamara L, Rosen MA, Hunt EA; International Network for Simulation-based Pediatric Innovation, Research and Education (INSPIRE) Collaborative. Epinephrine Auto-Injector Versus Drawn Up Epinephrine for Anaphylaxis Management: A Scoping Review. Pediatr Crit Care Med. 2017 Aug;18(8):764-769. doi: 10.1097/PCC.0000000000001197. Review. PubMed PMID: 28492400.
3: Morales-Cané I, Valverde-León MD, Rodríguez-Borrego MA. Epinephrine in cardiac arrest: systematic review and meta-analysis. Rev Lat Am Enfermagem. 2016 Dec 8;24:e2821. doi: 10.1590/1518-8345.1317.2821. Review. English, Portuguese, Spanish. PubMed PMID: 27982306; PubMed Central PMCID: PMC5171778.
4: Verberne AJ, Korim WS, Sabetghadam A, Llewellyn-Smith IJ. Adrenaline: insights into its metabolic roles in hypoglycaemia and diabetes. Br J Pharmacol. 2016 May;173(9):1425-37. doi: 10.1111/bph.13458. Epub 2016 Mar 8. Review. PubMed PMID: 26896587; PubMed Central PMCID: PMC4831313.
