An endogenous adrenergic receptor agonist
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(–)-Epinephrine

Item No. 18626

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
CAS Number
51-43-4
Synonyms
  • Adrenaline
  • NSC 62786
Molecular Formula
C9H13NO3
Formula Weight
183.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
λmax
281 nm
SMILES
OC1=C(O)C=CC([C@@H](O)CNC)=C1
InChi Code
InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
InChi Key
UCTWMZQNUQWSLP-VIFPVBQESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $75

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    10 g

    $134

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    25 g

    $295

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    Product Description

    (–)-Epinephrine is an endogenous adrenergic receptor agonist that is released from the adrenal medulla.1 It binds to α1-adrenergic receptors (Ki = 6 µg/L), as well as β1-, β2-, and β3-adrenergic receptors (Kis = 4, 7, and 126 µM, respectively) in radioligand binding assays.2,3 (–)-Epinephrine inhibits forskolin-induced adenylyl cyclase activity in CHO cells expressing α2-adrenergic receptors (EC50 = 240 nM) and induces cAMP production in primary human tracheal epithelial cells, which endogenously express β2-adrenergic receptors (EC50 = 640 nM).4,5 (–)-Epinephrine (100 µg/kg) reduces ear hyperperfusion and decreases in body temperature and increases survival in a mouse model of anaphylaxis induced by platelet-activating factor (PAF).6 Formulations containing (–)-epinephrine have been used in the treatment of anaphylaxis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rothman, R.B., Vu, N., Partilla, J.S., et al. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther. 307(1), 138-145 (2003).

    2. Farley, D.B., Ford, S.P., Reynolds, L.P., et al. Quantitation of α1-adrenergic receptors in porcine uterine and mesenteric arteries. Am. J. Obstet. Gynecol. 150(5 Pt. 1), 485-491 (1984).

    3. Hoffmann, C., Leitz, M.R., Oberdorf-Maass, S., et al. Comparative pharmacology of human β-adrenergic receptor subtypes—characterization of stably transfected receptors in CHO cells. N.-S. Arch. Pharmacol. 369(2), 151-159 (2004).

    4. Eason, M.G., and Liggett, S.B. Subtype-selective desensitization of α2-adrenergic receptors. Different mechanisms control short and long term agonist-promoted desensitization of α2C10, α2C4, and α2C2. The Journal of Biological Chemisty 267(35), 25473-25479 (1992).

    5. Davis, P.B., Silski, C.L., Kercsmar, C.M., et al. β-adrenergic receptors on human tracheal epithelial cells in primary culture. Am. J. Physiol. 258(1 Pt. 1), C71-C76 (1990).

    6. Ma, X., Xiaokaiti, Y., Lei, H., et al. Epinephrine inhibits vascular hyperpermeability during platelet-activating factor- or ovalbumin-induced anaphylaxis. RSC Adv. 83(7), 52762-52771 (2017).

    Product Citations

    Lewis, V., Bonniwell, E.M., Lanham, J.K., et al. A non-hallucinogenic LSD analog with therapeutic potential for mood disorders. Cell Rep. 42(3), 112203 (2023).