A reversible α2-adrenergic receptor antagonist
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Alternative(s)
46130Rauwolscine
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Rauwolscine (hydrochloride)

Item No. 15596

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(16β,17α,20α)-17-hydroxy-yohimban-16-carboxylic acid, methyl ester, monohydrochloride
CAS Number
6211-32-1
Synonyms
  • Isoyohimbine
  • NSC 407307
  • α-Yohimbine
Molecular Formula
C21H26N2O3 • HCl
Formula Weight
390.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.1 mg/mlDMSO: 2 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
λmax
223, 281 nm
SMILES
[H][C@]12N(CCC3=C2NC4=C3C=CC=C4)C[C@@]5([H])CC[C@H](O)[C@@H](C(OC)=O)[C@@]5([H])C1.Cl
InChi Code
InChI=1S/C21H26N2O3.ClH/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1H/t12-,15+,17+,18+,19+;/m1./s1
InChi Key
PIPZGJSEDRMUAW-ZKKXXTDSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $41

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    100 mg

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    250 mg

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    Product Description

    Rauwolscine is a natural alkaloid that acts as a selective and reversible α2-adrenergic receptor antagonist (Ki = 12 nM).1 It is a stereoisomer of yohimbine, which potently antagonizes both α1- and α2-adrenergic receptors.1 Rauwolscine also acts as a receptor antagonist at the serotonin 5-HT2B receptor (Ki = 14.3 nM) and as a weak partial agonist at 5-HT1A (IC50 = 1.3 µM).2,3,4 The α2-adrenergic receptor has diverse physiological functions and antagonists like rauwolscine have numerous applications, including the modulation of mood and behavior.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Perry, B.D., and U'Prichard, D.C. [3H]rauwolscine (α-yohimbine): A specific antagonist radioligand for brain α2-adrenergic receptors. Eur. J. Pharmacol. 76(4), 461-464 (1981).

    2. Kaumann, A.J. Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch. Pharmacol. 323(2), 149-154 (1983).

    3. Arthur, J.M., Casañas, S.J., and Raymond, J.R. Partial agonist properties of rauwolscine and yohimbine for the inhibition of adenylyl cyclase by recombinant human 5-HT1A receptors. Biochem. Pharmacol. 45(11), 2337-2341 (1993).

    4. Wainscott, D.B., Sasso, D.A., Kursar, J.D., et al. [3H]Rauwolscine: An antagonist radioligand for the cloned human 5-hydroxytryptamine2B (5-HT2B) receptor. Naunyn Schmiedebergs Arch. Pharmacol. 357(1), 17-24 (1998).

    5. Brede, M., Philipp, M., Knaus, A., et al. α2-adrenergic receptor subtypes - novel functions uncovered in gene-targeted mouse models. Biol. Cell 96(5), 343-348 (2004).

    6. Cottingham, C., and Wang, Q. α2 adrenergic receptor dysregulation in depressive disorders: Implications for the neurobiology of depression and antidepressant therapy. Neurosci. Biobehav. Rev. 36(10), 2214-2225 (2012).