Rauwolscine hydrochloride

Modify Date: 2024-01-03 17:07:14

Rauwolscine hydrochloride structure	Common Name	Rauwolscine hydrochloride
	CAS Number	6211-32-1	Molecular Weight	390.904
	Density	1.31 g/cm3	Boiling Point	543ºC at 760 mmHg
	Molecular Formula	C₂₁H₂₇ClN₂O₃	Melting Point	270-280ºC
	MSDS	N/A	Flash Point	282.2ºC

Use of Rauwolscine hydrochloride

Rauwolscine hydrochloride is a potent and specific α2 adrenergic receptor antagonist with a Ki of 12 nM.

Name	rauwolscine hydrochloride
Synonym	More Synonyms

Description	Rauwolscine hydrochloride is a potent and specific α2 adrenergic receptor antagonist with a Ki of 12 nM.
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research Areas >> Neurological Disease
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

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)