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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O3
Molecular Weight 354.4435
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-YOHIMBINE

SMILES

COC(=O)[C@@]1([H])[C@@]2([H])C[C@@]3([H])c4c(CCN3C[C@@]2([H])CC[C@]1([H])O)c5ccccc5[nH]4

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

Molecular Formula C21H26N2O3
Molecular Weight 354.4435
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.

CNS Activity

Curator's Comment:: referenced study was conducted in rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
1992 Apr 15
Pharmacological characteristics of alpha 2-adrenergic receptors: comparison of pharmacologically defined subtypes with subtypes identified by molecular cloning.
1992 Jul
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
Characterization of a novel tetrandrine-induced contraction in rat tail artery.
2002 Aug
Evidence that the novel imidazoline compound FT005 is an alpha(2)-adrenoceptor agonist.
2002 Aug
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
Prior iontophoresis of saline enhances vasoconstriction to phenylephrine and clonidine in the skin of the human forearm.
2002 Jul
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
Neurotransmitter release in an arterial preparation and the action of alpha-adrenoceptor antagonists.
2002 Oct-Dec
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
Pharmacological characterization of alpha 2-adrenoceptor-mediated responses in pig nasal mucosa.
2003 Aug
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 Aug
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
Moxonidine displays a presynaptic alpha-2-adrenoceptor-dependent synergistic sympathoinhibitory action at imidazoline-1 receptors.
2003 Dec
No evidence for activation of alpha(2)-adrenoceptors by methanolic extracts of bovine brain and lung containing clonidine-displacing substance.
2003 Dec
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
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
Effect of the vascular endothelium on contractions induced by noradrenaline and phenylephrine in perforating branch of the human internal mammary artery.
2003 Jul-Aug
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
Enhanced noradrenergic transmission in the spontaneously hypertensive rat anococcygeus muscle.
2003 Oct
alpha2a adrenoceptors regulate phosphorylation of microtubule-associated protein-2 in cultured cortical neurons.
2004
Immunohistochemical and functional evidence for a noradrenergic regulation in the horse penile deep dorsal vein.
2004 Dec
5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine.
2004 Jan 26
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
2004 Jan 26
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
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
Epinephrine-induced hyperpolarization of islet cells without KATP channels.
2004 Mar
Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats.
2004 May 14
alpha-Adrenoceptor subtypes mediating regional kidney blood flow responses to renal nerve stimulation.
2004 May 31
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
Phenylpropanolamine constricts mouse and human blood vessels by preferentially activating alpha2-adrenoceptors.
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
Role of adrenergic receptors in the reflex diuresis in rabbits during pulmonary lymphatic obstruction.
2005 May
Patents

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 Sat Jun 26 15:37:51 UTC 2021
Edited
by admin
on Sat Jun 26 15:37:51 UTC 2021
Record UNII
T4LJ7LU45W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.ALPHA.-YOHIMBINE
MI  
Common Name English
YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, (16.BETA.,17.ALPHA.,20.ALPHA.)-
Common Name English
METHYL 17.ALPHA.-HYDROXY-20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE
Systematic Name English
MESO-YOHIMBINE
Common Name English
YOHIMBINE HYDROCHLORIDE IMPURITY B [EP]
Common Name English
MESOYOHIMBINE
Common Name English
ISOYOHIMBINE
Common Name English
.ALPHA.-YOHIMBINE [EP]
Common Name English
.ALPHA.-YOHIMBINE [MI]
Common Name English
YOHIMBINE, .ALPHA.-
Common Name English
RAUWOLSCINE
Common Name English
CORYNANTHIDINE
Common Name English
Classification Tree Code System Code
DSLD 2781 (Number of products:85)
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
Code System Code Type Description
FDA UNII
T4LJ7LU45W
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
PRIMARY
WIKIPEDIA
Rauwolscine
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
PRIMARY
PUBCHEM
643606
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
PRIMARY
EPA CompTox
131-03-3
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-006-9
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
PRIMARY
CAS
131-03-3
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
PRIMARY
MERCK INDEX
M11571
Created by admin on Sat Jun 26 15:37:51 UTC 2021 , Edited by admin on Sat Jun 26 15:37:51 UTC 2021
PRIMARY Merck Index
Related Record Type Details
TARGET -> AGONIST
SHORT-ACTING
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY