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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O3
Molecular Weight 354.4427
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-YOHIMBINE

SMILES

[H][C@]12CC[C@H](O)[C@@H](C(=O)OC)[C@@]1([H])C[C@]3([H])N(CCC4=C3NC5=C4C=CC=C5)C2

InChI

InChIKey=BLGXFZZNTVWLAY-DIRVCLHFSA-N
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

HIDE SMILES / InChI

Description

alpha-yohmbine (aka rauwloscine) is a diastereomer of yohimbine and shares many of the same properties. Rauwolscine acts as an alpha-2-adrenergic antagonist and is therefore used as an unregulated nutritional supplement for fat-burning and CNS stimulation. Rauwolscine is also an antagonist of the HT2B receptor and has been investigated for the potential to mitigate blood vessel spasms.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.5 nM [Kd]
14.3 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
The effect of rauwolscine was found to antagonize clonidine-induced hypoactivity in rats in a dose range of 0.3 - 3 mg/kg delivered intraperitoneally.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Human Umbilical Vein Endothelial Cells (HUVEC's) were incubated with phenol red-free M 199 medium for 60 min then loaded with 5 micro-M DAF-FM diacetate for 30 min at 37 deg-C. The cells were washed and then treated at room temperature with agmatine for 10 min in the presence and absence of 0.2 nM rauwolscine. Cellular fluorescence was measured to monitor Nitrous Oxide production. Rauwolscine demonstrated a potent antagonistic effect for the production of NO.