CAS 65-19-0|Yohimbine hydrochloride

Introduction：Basic information about CAS 65-19-0|Yohimbine hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Yohimbine hydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles35
8. Synonyms

Common Name	Yohimbine hydrochloride
CAS Number	65-19-0	Molecular Weight	390.904
Density	/	Boiling Point	542.979ºC at 760 mmHg
Molecular Formula	C₂₁H₂₇ClN₂O₃	Melting Point	288-290 °C (dec.)(lit.)
MSDS	ChineseUSA	Flash Point	282.184ºC
Symbol	GHS06	Signal Word	Danger

Names

Name	Yohimbine hydrochloride
Synonym	More Synonyms

Yohimbine hydrochloride BiologicalActivity

Description	Yohimbine hydrochloride is an alpha 2-adrenoreceptor antagonist, blocking the pre- and postsynaptic alpha-2 adrenoreceptors and causing an increased release of noradrenaline and dopamine.IC50 value:Target:In vitro:In vivo: Yohimbine hydrochloride (0.2 mg/kg, i.p.) was administered to rats 1h before the stress session daily for 14 consecutive days and its effect was assessed. Results of this section revealed that, immersion of rats in cold water significantly decreased sexual arousal and motivation as indicated by increased latencies and intervals. Decreased copulatory activity was confirmed by decreased testosterone, luteinizing hormone (LH) and follicle-stimulating-hormone (FSH) levels as well as decreased cholesterol content in rat testes. Treatment with yohimbine significantly increased the sexual arousal and potency and corrected the effects induced by stress on the mating behavior of male rats [1].
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorNatural Products >>AlkaloidResearch Areas >>Others
References	[1]. Saad MA, et al. Potential effects of yohimbine and sildenafil on erectile dysfunction in rats. [2]. Docherty JR. Yohimbine antagonises α1A- and α1D-adrenoceptor mediated components in addition to the α2A-adrenoceptor component to pressor responses in the pithed rat. Eur J Pharmacol. 2012 Mar 15;679(1-3):90-4. [3]. Lahiri P, et al. Platelet responsiveness to yohimbine hydrochloride and MRS2179 in the context of the interaction between collagen and epinephrine in acute coronary syndrome. Blood Cells Mol Dis. 2009 Jul-Aug;43(1):105-10.

Description

Yohimbine hydrochloride is an alpha 2-adrenoreceptor antagonist, blocking the pre- and postsynaptic alpha-2 adrenoreceptors and causing an increased release of noradrenaline and dopamine.IC50 value:Target:In vitro:In vivo: Yohimbine hydrochloride (0.2 mg/kg, i.p.) was administered to rats 1h before the stress session daily for 14 consecutive days and its effect was assessed. Results of this section revealed that, immersion of rats in cold water significantly decreased sexual arousal and motivation as indicated by increased latencies and intervals. Decreased copulatory activity was confirmed by decreased testosterone, luteinizing hormone (LH) and follicle-stimulating-hormone (FSH) levels as well as decreased cholesterol content in rat testes. Treatment with yohimbine significantly increased the sexual arousal and potency and corrected the effects induced by stress on the mating behavior of male rats [1].

Related Catalog

Signaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorNatural Products >>AlkaloidResearch Areas >>Others

References

[1]. Saad MA, et al. Potential effects of yohimbine and sildenafil on erectile dysfunction in rats.

[2]. Docherty JR. Yohimbine antagonises α1A- and α1D-adrenoceptor mediated components in addition to the α2A-adrenoceptor component to pressor responses in the pithed rat. Eur J Pharmacol. 2012 Mar 15;679(1-3):90-4.

[3]. Lahiri P, et al. Platelet responsiveness to yohimbine hydrochloride and MRS2179 in the context of the interaction between collagen and epinephrine in acute coronary syndrome. Blood Cells Mol Dis. 2009 Jul-Aug;43(1):105-10.

Chemical & Physical Properties

Boiling Point	542.979ºC at 760 mmHg
Melting Point	288-290 °C (dec.)(lit.)
Molecular Formula	C₂₁H₂₇ClN₂O₃
Molecular Weight	390.904
Flash Point	282.184ºC
Exact Mass	390.171021
PSA	65.56000
LogP	3.38700
Index of Refraction	103 ° (C=1, H2O)
InChIKey	PIPZGJSEDRMUAW-VJDCAHTMSA-N
SMILES	COC(=O)C1C(O)CCC2CN3CCc4c([nH]c5ccccc45)C3CC21.Cl
Storage condition	2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ZG1015000

CHEMICAL NAME :: Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester, hydrochloride

CAS REGISTRY NUMBER :: 65-19-0

LAST UPDATED :: 199712

DATA ITEMS CITED :: 13

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 -17A

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 133 ug/kg

TOXIC EFFECTS :: Behavioral - euphoria

REFERENCE :: AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 141,1267,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Behavioral - euphoria Behavioral - hallucinations, distorted perceptions

REFERENCE :: AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 141,1267,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 55 mg/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Autonomic Nervous System - central sympatholytic

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 110,20,1957

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 51,345,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 45 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4179510

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 43900 ug/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold

REFERENCE :: BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 21,51,1963

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 50,241,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Autonomic Nervous System - other (direct) parasympathomimetic 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 :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5 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 :: 42 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 :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 137,305,1943

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 26 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

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H300-H311-H331
Precautionary Statements	P261-P264-P280-P301 + P310-P311
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T
Risk Phrases	R23/24;R33
Safety Phrases	S22-S36/37/39-S45-S24/25
RIDADR	UN 1544 6.1/PG 2
WGK Germany	3
RTECS	ZG1015000
Packaging Group	II
Hazard Class	6.1(a)
HS Code	2933990090

Customs

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Synonyms

UNII-NB2E1YP49F

Yohimbe HCl

(16α,17α)-17-Hydroxyyohimban-16-carboxylate de méthyle chlorhydrate

(1R,2S,4aR,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

Yohimbine hydrochloride

Methyl (16α,17α)-17-hydroxyyohimban-16-carboxylate hydrochloride

Methyl (16α,17α)-17-hydroxyyohimban-16-carboxylate hydrochloride (1:1)

MFCD00012674

Yohimbine HCl

Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16α,17α)-, hydrochloride (1:1)

Yohimban-16α-carboxylic acid, 17α-hydroxy-, methyl ester, monohydrochloride

Antagonil

Yohimban-16α-carboxylic acid, 17α-hydroxy-, methyl ester, monohydrochloride (8CI)

Aphrodyne

Methyl (1R,2S,4aR,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

EINECS 200-600-4

Methyl-(1R,2S,4aR,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

Yohimbine monohydrochloride

Yohimbine (Hydrochloride)

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