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6211-32-1

6211-32-1 structure
6211-32-1 structure
  • Name: Rauwolscine hydrochloride
  • Chemical Name: rauwolscine hydrochloride
  • CAS Number: 6211-32-1
  • Molecular Formula: C21H27ClN2O3
  • Molecular Weight: 390.904
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-07-30 19:51:17
  • Modify Date: 2025-08-25 08:56:25
  • Rauwolscine hydrochloride is a potent and specific α2 adrenergic receptor antagonist with a Ki of 12 nM.
Name rauwolscine hydrochloride
Synonyms isoyohimbine
20α-Yohimban-16β-carboxylic acid, 17α-hydroxy-, methyl ester, monohydrochloride (8CI)
EINECS 228-279-6
rauwolscine
Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (15ξ,16β,17α,20α)-, hydrochloride (1:1)
Methyl (15ξ,16β,17α,20α)-17-hydroxyyohimban-16-carboxylate hydrochloride (1:1)
Methyl (1S,2S,4aS,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate hydrochloride
Methyl-(1S,2S,4aS,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isochinolin-1-carboxylathydrochlorid
mesoyohimbine
Methyl (16β,17α,20α)-17-hydroxyyohimban-16-carboxylate hydrochloride (1:1)
Methyl (16β,17α,20α)-17-hydroxyyohimban-16-carboxylate hydrochloride
(16β,17α,20α)-17-Hydroxyyohimban-16-carboxylate de méthyle chlorhydrate
rauwolfscine hydrochloride
20α-Yohimban-16β-carboxylic acid, 17α-hydroxy-, methyl ester, monohydrochloride
Methyl-(16β,17α,20α)-17-hydroxyyohimban-16-carboxylathydrochlorid
(1S,2S,4aS,13bS,14aS)-2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodécahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoléine-1-carboxylate de méthyle chlorhydrate
rauwolscine hcl
Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16β,17α,20α)-, hydrochloride (1:1)
Rauwolscine (hydrochloride)
Description Rauwolscine hydrochloride is a potent and specific α2 adrenergic receptor antagonist with a Ki of 12 nM.
Related Catalog
Target

Ki: 12 nM (α2 adrenergic receptor)[1]

In Vitro [3H]Rauwolscine binding to α2 adrenergic receptor is reversible, stcreospccific, and saturable. [3H]Rauwolscine specifically labels both the high and low affinity states of the α2 adrenergic receptor in brain membranes[1]. [3H]Rauwolscine also behaves as a 5-HT1A receptor agonist and this conclusion is compatible with earlier functional studies, indicating that rauwolscine (as well as yohimbine) has agonistic properties at the level of 5-HT autoreceptors[2]. When using [3H]5-HT as a radioligand, rauwolscine is determined to have relatively high affinity for the human receptor (Ki human=14.3 nM, Ki rat=35.8 nM)[3]. Saturation studies shows that the affinity of [3H]Rauwolscine is similar in mouse, rat, rabbit, dog (2.33-3.03 nM) except man where it is significantly higher (0.98 nM) [4].
Kinase Assay Fresh bovine frontal cortex is incubated in triplicate with [3H]Rauwolscine (82 Ci/mM, diluted). Incubation is terminated by filtration under reduced pressure over filters, which are then rinsed with ice cold Tris-HCl buffer, dried overnight and added to disposable glass minivials containing 3.0 mL of a 95% Econofluor/5% Protosol solution. Samples are counted by liquid scintillation spectrometry with an efficiency of 32%. (-)- [3H]Epinephrine binding to bovine cortex membranes is conducted at 25°C[1].
References

[1]. Perry BD, et al. [3H]rauwolscine (alpha-yohimbine): a specific antagonist radioligand for brain alpha 2-adrenergic receptors. Eur J Pharmacol. 1981 Dec 17;76(4):461-4.

[2]. De Vos H, et al. [3H]rauwolscine behaves as an agonist for the 5-HT1A receptors in human frontal cortex membranes. Eur J Pharmacol. 1991 May 25;207(1):1-8.

[3]. Wainscott DB, et al. [3H]Rauwolscine: an antagonist radioligand for the cloned human 5-hydroxytryptamine2b (5-HT2B) receptor. Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):17-24.

[4]. Neylon CB, et al. [3H]-rauwolscine binding to alpha 2-adrenoceptors in the mammalian kidney: apparent receptor heterogeneity between species. Br J Pharmacol. 1985 Jun;85(2):349-59.
Density 1.31 g/cm3
Boiling Point 543ºC at 760 mmHg
Melting Point 270-280ºC
Molecular Formula C21H27ClN2O3
Molecular Weight 390.904
Flash Point 282.2ºC
Exact Mass 390.171021
PSA 65.56000
LogP 3.38700
Storage condition Store at RT
Water Solubility H2O: soluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
ZG1035000
CHEMICAL NAME :
20-alpha-Yohimban-16-beta-carboxylic acid, 17-alpha-hydroxy-, methyl ester, hydrochloride
CAS REGISTRY NUMBER :
6211-32-1
LAST UPDATED :
199203
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C21-H26-N2-O3.Cl-H
MOLECULAR WEIGHT :
390.95
WISWESSER LINE NOTATION :
T F6 D5 C666 EM ON&&TTTJ TQ UVO1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
125 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
LDBU** "Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932 Volume(issue)/page/year: -,-,1932
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Behavioral - general anesthetic Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
LDBU** "Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932 Volume(issue)/page/year: -,-,1932
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
LDBU** "Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932 Volume(issue)/page/year: -,-,1932
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
162 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BSPHAV Bulletin des Sciences Pharmacologiques. (Paris, France) V.1-49, 1899-1942. For publisher information, see APFRAD. Volume(issue)/page/year: 47,33,1940
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BSPHAV Bulletin des Sciences Pharmacologiques. (Paris, France) V.1-49, 1899-1942. For publisher information, see APFRAD. Volume(issue)/page/year: 47,33,1940
Hazard Codes T: Toxic;
Risk Phrases R23/24/25
Safety Phrases 22-36/37/39-45
RIDADR UN 1544 6
WGK Germany 3
RTECS ZG1035000
HS Code 29339900
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