A monoterpene indole alkaloid with cardiovascular activities
Related Products
Alternative(s)
15596Rauwolscine (hydrochloride)
Diastereomer(s)
19869Yohimbine (hydrochloride)
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Rauwolscine

Item No. 46130

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(16β,17α,20α)-17-hydroxy-yohimban-16-carboxylic acid, methyl ester
CAS Number
131-03-3
Synonyms
  • Isoyohimbine
  • Corynanthidine
  • α-Yohimbine
Molecular Formula
C21H26N2O3
Formula Weight
354.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/ml
SMILES
O=C([C@H]1[C@@]2([H])C[C@@]3([H])C4=C(CCN3C[C@@]2([H])CC[C@@H]1O)C5=CC=CC=C5N4)OC
InChi Code
InChI=1S/C21H26N2O3/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/t12-,15+,17+,18+,19+/m1/s1
InChi Key
BLGXFZZNTVWLAY-DIRVCLHFSA-N
Origin
Plant/Rauwolfia vomitoria
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Rauwolscine is a monoterpene indole alkaloid that has been found in R. tetraphylla and has cardiovascular activities.1,2,3,4,5 It is an antagonist of the α2-adrenergic receptor and serotonin (5-HT) receptor subtype 5-HT2B (Kis = 4 and 14.3 nM, respectively) and a partial agonist of the 5-HT1A receptor (IC50 = 1.5 µM).2,3,4 Rauwolscine (1 and 3 µg/kg) restores electrically induced tachycardia after inhibition by clonidine (Item No. 15949) and inhibits hypertension induced by phenylephrine in anesthetized dogs.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stander, E.A., Lehka, B., Carqueijeiro, I., et al. The Rauvolfia tetraphylla genome suggests multiple distinct biosynthetic routes for yohimbane monoterpene indole alkaloids. Commun. Biol. 6(1), 1197 (2023).

    2. 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).

    3. 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).

    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. Shepperson, N.B., Duval, N., Massingham, R., et al. Pre- and postsynaptic alpha adrenoceptor selectivity studies with yohimbine and its two diastereoisomers rauwolscine and corynanthine in the anesthetized dog. J. Pharmacol. Exp. Ther. 219(2), 540-546 (1981).