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
[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
| 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 |
|---|---|---|
| Involvement of noradrenergic innervation from locus coeruleus to hippocampal formation in negative feedback regulation of penile erection in the rat. | 2001 |
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| Regarding the unitary theory of agonist and antagonist action at presynaptic adrenoceptors. | 2001 Jun |
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| Circadian change of adenylate cyclase activity in rabbit ciliary processes. | 2001 Oct |
|
| Neuropeptide Y inhibits double peaked vasoconstrictor responses to periarterial nerve stimulation primarily through prejunctional Y2 receptor subtype in canine splenic arteries. | 2002 Apr |
|
| Alpha2-adrenoceptor ligands inhibit alpha1-adrenoceptor-mediated contraction of isolated rat arteries. | 2002 Aug |
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| Characterization of a novel tetrandrine-induced contraction in rat tail artery. | 2002 Aug |
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| Evidence that the novel imidazoline compound FT005 is an alpha(2)-adrenoceptor agonist. | 2002 Aug |
|
| Presynaptic effects of moxonidine in isolated buffer perfused rat hearts: role of imidazoline-1 receptors and alpha2-adrenoceptors. | 2002 Dec |
|
| Agmatine inhibits arginine vasopressin-stimulated urea transport in the rat inner medullary collecting duct. | 2002 Dec |
|
| Alpha 2-adrenoceptors in the enteric nervous system: a study in alpha 2A-adrenoceptor-deficient mice. | 2002 Feb |
|
| Noradrenaline release-inhibiting receptors on PC12 cells devoid of alpha(2(-)) and CB(1) receptors: similarities to presynaptic imidazoline and edg receptors. | 2002 Feb |
|
| 5-Isothiocyanato-2-benzofuranyl-2-imidazoline (BU99006) an irreversible imidazoline(2) binding site ligand: in vitro and in vivo characterisation in rat brain. | 2002 Jul |
|
| Dual alpha(2)-adrenergic agonist and alpha(1)-adrenergic antagonist actions of dexmedetomidine on human isolated endothelium-denuded gastroepiploic arteries. | 2002 Jun |
|
| Functional characterization of serotonin receptors in rat isolated aorta. | 2002 May |
|
| Pharmacological evidence of a role for prejunctional imidazoline (I(1)) receptors in ocular function. | 2002 Nov |
|
| Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina. | 2002 Nov 1 |
|
| Effects of medullary alpha2-adrenoceptor blockade in the rat. | 2002 Oct 25 |
|
| Identification and characterization of the imidazoline I2b-binding sites in the hamster brown adipose tissue as a study model for imidazoline receptors. | 2003 Apr |
|
| Pharmacological profile of the vascular responses to dopamine in the canine external carotid circulation. | 2003 Apr |
|
| Crosstalk between presynaptic angiotensin receptors, bradykinin receptors and alpha 2-autoreceptors in sympathetic neurons: a study in alpha 2-adrenoceptor-deficient mice. | 2003 Apr |
|
| Differential regulation of rat peripheral 5-HT(2A) and 5-HT(2B) receptor systems: influence of drug treatment. | 2003 Aug |
|
| 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 Aug |
|
| All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. | 2003 Dec |
|
| Alpha-2 adrenergic receptors stimulate actin organization in developing fetal rat cardiac myocytes. | 2003 Feb 14 |
|
| Involvement of a purinergic pathway in the sympathetic regulation of motility in rat ileum. | 2003 Feb 28 |
|
| Adrenergic mechanisms in canine nasal venous systems. | 2003 Jan |
|
| Effects of chronic systemic hypoxia on contraction evoked by noradrenaline in the rat iliac artery. | 2003 Jul |
|
| Pharmacological characterization of unique prazosin-binding sites in human kidney. | 2003 Jul |
|
| Functional characterization of alpha-adrenoceptors mediating pupillary dilation in rats. | 2003 Jun 20 |
|
| Existence of alpha-adrenoceptor subtypes in isolated human gastroepiploic and omental arteries. | 2003 Mar |
|
| Altered prejunctional modulation of intestinal cholinergic and noradrenergic pathways by alpha2-adrenoceptors in the presence of experimental colitis. | 2003 May |
|
| Possible role of alpha-adrenoceptor subtypes in acute migraine therapy. | 2003 May |
|
| 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 Nov |
|
| Different pharmacological properties of two equipotent antagonists (clozapine and rauwolscine) for 5-HT2B receptors in rat stomach fundus. | 2003 Sep 15 |
|
| Augmentation of moxonidine-induced increase in ANP release by atrial hypertrophy. | 2004 Jul |
|
| Small molecules targeting severe acute respiratory syndrome human coronavirus. | 2004 Jul 6 |
|
| LNP 906, the first high-affinity photoaffinity ligand selective for I1 imidazoline receptors. | 2004 Jun |
|
| Assessment of anti-migraine potential of a novel alpha-adrenoceptor agonist S19014: effects on porcine carotid and regional haemodynamics and human coronary artery. | 2004 Jun |
|
| Protein kinase C regulates alpha(2A/D)-adrenoceptor constitutive activity. | 2004 Jun |
|
| Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. | 2004 May 14 |
|
| 3H-Noradrenaline release from mouse iris-ciliary body: role of presynaptic muscarinic heteroreceptors. | 2004 Oct |
|
| Dexmedetomidine produces its neuroprotective effect via the alpha 2A-adrenoceptor subtype. | 2004 Oct 11 |
|
| Reduction of vascular noradrenaline sensitivity by AT1 antagonists depends on functional sympathetic innervation. | 2004 Sep |
|
| A search for presynaptic beta3-adrenoceptors in the rat. | 2005 Apr |
|
| Fentanyl attenuates alpha1B-adrenoceptor-mediated pulmonary artery contraction. | 2005 Aug |
|
| Two "knockout" mouse models demonstrate that aortic vasodilatation is mediated via alpha2a-adrenoceptors located on the endothelium. | 2005 Aug |
|
| Neurogenic double-peaked vasoconstriction of human gastroepiploic artery is mediated by both alpha1- and alpha2-adrenoceptors. | 2005 Mar |
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
Thu Jul 06 15:41:23 UTC 2023
by
admin
on
Thu Jul 06 15:41:23 UTC 2023
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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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2781 (Number of products:85)
Created by
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| Code System | Code | Type | Description | ||
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48562
Created by
admin on Thu Jul 06 15:41:23 UTC 2023 , Edited by admin on Thu Jul 06 15:41:23 UTC 2023
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T4LJ7LU45W
Created by
admin on Thu Jul 06 15:41:23 UTC 2023 , Edited by admin on Thu Jul 06 15:41:23 UTC 2023
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Rauwolscine
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admin on Thu Jul 06 15:41:23 UTC 2023 , Edited by admin on Thu Jul 06 15:41:23 UTC 2023
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643606
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admin on Thu Jul 06 15:41:23 UTC 2023 , Edited by admin on Thu Jul 06 15:41:23 UTC 2023
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DTXSID2045608
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205-006-9
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131-03-3
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M11571
Created by
admin on Thu Jul 06 15:41:23 UTC 2023 , Edited by admin on Thu Jul 06 15:41:23 UTC 2023
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
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TARGET -> AGONIST |
SHORT-ACTING
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| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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|---|---|---|---|---|
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ACTIVE MOIETY |
