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
SMILES
COC(=O)[C@@H]1[C@@H](O)CC[C@@H]2CN3CCC4=C(NC5=C4C=CC=C5)[C@@H]3C[C@H]12
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
| Molecular Formula | C21H26N2O3 |
| Molecular Weight | 354.4427 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P08913 Gene ID: 150.0 Gene Symbol: ADRA2A Target Organism: Homo sapiens (Human) |
2.5 nM [Kd] | ||
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) |
14.3 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fentanyl attenuates alpha1B-adrenoceptor-mediated pulmonary artery contraction. | 2005-08 |
|
| Two "knockout" mouse models demonstrate that aortic vasodilatation is mediated via alpha2a-adrenoceptors located on the endothelium. | 2005-08 |
|
| Role of adrenergic receptors in the reflex diuresis in rabbits during pulmonary lymphatic obstruction. | 2005-05 |
|
| A search for presynaptic beta3-adrenoceptors in the rat. | 2005-04 |
|
| Phenylpropanolamine constricts mouse and human blood vessels by preferentially activating alpha2-adrenoceptors. | 2005-04 |
|
| Neurogenic double-peaked vasoconstriction of human gastroepiploic artery is mediated by both alpha1- and alpha2-adrenoceptors. | 2005-03 |
|
| Immunohistochemical and functional evidence for a noradrenergic regulation in the horse penile deep dorsal vein. | 2004-12 |
|
| Dexmedetomidine produces its neuroprotective effect via the alpha 2A-adrenoceptor subtype. | 2004-10-11 |
|
| 3H-Noradrenaline release from mouse iris-ciliary body: role of presynaptic muscarinic heteroreceptors. | 2004-10 |
|
| Reduction of vascular noradrenaline sensitivity by AT1 antagonists depends on functional sympathetic innervation. | 2004-09 |
|
| Small molecules targeting severe acute respiratory syndrome human coronavirus. | 2004-07-06 |
|
| 5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs. | 2004-07 |
|
| Augmentation of moxonidine-induced increase in ANP release by atrial hypertrophy. | 2004-07 |
|
| LNP 906, the first high-affinity photoaffinity ligand selective for I1 imidazoline receptors. | 2004-06 |
|
| Assessment of anti-migraine potential of a novel alpha-adrenoceptor agonist S19014: effects on porcine carotid and regional haemodynamics and human coronary artery. | 2004-06 |
|
| Protein kinase C regulates alpha(2A/D)-adrenoceptor constitutive activity. | 2004-06 |
|
| alpha-Adrenoceptor subtypes mediating regional kidney blood flow responses to renal nerve stimulation. | 2004-05-31 |
|
| Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. | 2004-05-14 |
|
| Epinephrine-induced hyperpolarization of islet cells without KATP channels. | 2004-03 |
|
| 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. | 2004-01-26 |
|
| Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor. | 2004-01-26 |
|
| [Effect of rilmenidine on intraocular pressure in rabbits, interaction with efaroxan and rauwolscine]. | 2004 |
|
| alpha2a adrenoceptors regulate phosphorylation of microtubule-associated protein-2 in cultured cortical neurons. | 2004 |
|
| Moxonidine displays a presynaptic alpha-2-adrenoceptor-dependent synergistic sympathoinhibitory action at imidazoline-1 receptors. | 2003-12 |
|
| No evidence for activation of alpha(2)-adrenoceptors by methanolic extracts of bovine brain and lung containing clonidine-displacing substance. | 2003-12 |
|
| All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. | 2003-12 |
|
| The aminotetraline derivative (+/-)-(R,S)-5,6-dihydroxy-2-methylamino-1,2,3,4-tetrahydro-naphthalene hydrochloride (CHF-1024) displays cardioprotection in postischemic ventricular dysfunction of the rat heart. | 2003-11 |
|
| Enhanced noradrenergic transmission in the spontaneously hypertensive rat anococcygeus muscle. | 2003-10 |
|
| Different pharmacological properties of two equipotent antagonists (clozapine and rauwolscine) for 5-HT2B receptors in rat stomach fundus. | 2003-09-15 |
|
| Pharmacological characterization of alpha 2-adrenoceptor-mediated responses in pig nasal mucosa. | 2003-08 |
|
| Fipamezole (JP-1730) is a potent alpha2 adrenergic receptor antagonist that reduces levodopa-induced dyskinesia in the MPTP-lesioned primate model of Parkinson's disease. | 2003-08 |
|
| Differential regulation of rat peripheral 5-HT(2A) and 5-HT(2B) receptor systems: influence of drug treatment. | 2003-08 |
|
| The role of I(1)-imidazoline and alpha(2)-adrenergic receptors in the modulation of glucose metabolism in the spontaneously hypertensive obese rat model of metabolic syndrome X. | 2003-08 |
|
| The functional alpha-adrenoceptor in dog caudal vesical arteries is mainly an alpha1A subtype. | 2003-07-18 |
|
| Neurotransmitter release in an arterial preparation and the action of alpha-adrenoceptor antagonists. | 2003-07-18 |
|
| Effects of chronic systemic hypoxia on contraction evoked by noradrenaline in the rat iliac artery. | 2003-07 |
|
| Pharmacological characterization of unique prazosin-binding sites in human kidney. | 2003-07 |
|
| Functional characterization of alpha-adrenoceptors mediating pupillary dilation in rats. | 2003-06-20 |
|
| Altered prejunctional modulation of intestinal cholinergic and noradrenergic pathways by alpha2-adrenoceptors in the presence of experimental colitis. | 2003-05 |
|
| Possible role of alpha-adrenoceptor subtypes in acute migraine therapy. | 2003-05 |
|
| Identification and characterization of the imidazoline I2b-binding sites in the hamster brown adipose tissue as a study model for imidazoline receptors. | 2003-04 |
|
| Pharmacological profile of the vascular responses to dopamine in the canine external carotid circulation. | 2003-04 |
|
| Crosstalk between presynaptic angiotensin receptors, bradykinin receptors and alpha 2-autoreceptors in sympathetic neurons: a study in alpha 2-adrenoceptor-deficient mice. | 2003-04 |
|
| Existence of alpha-adrenoceptor subtypes in isolated human gastroepiploic and omental arteries. | 2003-03 |
|
| Pharmacological evidence of a role for prejunctional imidazoline (I(1)) receptors in ocular function. | 2002-11 |
|
| Alpha2-adrenoceptor ligands inhibit alpha1-adrenoceptor-mediated contraction of isolated rat arteries. | 2002-08 |
|
| Neuropeptide Y inhibits double peaked vasoconstrictor responses to periarterial nerve stimulation primarily through prejunctional Y2 receptor subtype in canine splenic arteries. | 2002-04 |
|
| Effect of the vascular endothelium on contractions induced by noradrenaline and phenylephrine in perforating branch of the human internal mammary artery. | 2002-03-17 |
|
| Pharmacological characteristics of alpha 2-adrenergic receptors: comparison of pharmacologically defined subtypes with subtypes identified by molecular cloning. | 1992-07 |
|
| Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta. | 1992-04-15 |
Sample Use Guides
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
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:04:23 GMT 2025
by
admin
on
Mon Mar 31 23:04:23 GMT 2025
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| Record UNII |
T4LJ7LU45W
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| Record Status |
Validated (UNII)
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| Record Version |
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DSLD |
2781 (Number of products:85)
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48562
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T4LJ7LU45W
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Rauwolscine
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643606
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DTXSID2045608
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205-006-9
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131-03-3
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m11571
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
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TARGET -> AGONIST |
| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
