Yohimbine hydrochloride

Modify Date: 2026-07-02 09:31:43

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

 Use of Yohimbine hydrochloride


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].

 Names

Name Yohimbine hydrochloride
Synonym More Synonyms

 Yohimbine hydrochloride Biological Activity

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
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
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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 Yohimbine hydrochlorideBioassay

View more

Name: Primary cell-based high-throughput screening assay for identification of compounds th...
Source: Johns Hopkins Ion Channel Center
Target: regulator of G-protein signaling 4 isoform 2 [Homo sapiens]
External Id: JHICC_RGS_Act_HTS
Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN
Name: QFRET-based biochemical primary high throughput screening assay to identify exosite i...
Source: The Scripps Research Institute Molecular Screening Center
Target: disintegrin and metalloproteinase domain-containing protein 17 preproprotein [Homo sapiens]
External Id: ADAM17_INH_QFRET_1536_1X%INH PRUN
Name: Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay
Source: ChEMBL
Target: N/A
External Id: CHEMBL1266185
Name: ERK5 transcriptional activity HTS
Source: 24565
Target: N/A
External Id: ERK5 transcriptional activity-HTS
Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
Name: uHTS identification of small molecule activators of the adaptive arm of the Unfolded ...
Source: Burnham Center for Chemical Genomics
Target: N/A
External Id: BCCG-A405-UPR-XBP1-PrimaryAgonist-Assay
Name: Fluorescence polarization to screen for inhibitor that competite the binding of FadD2...
Source: Broad Institute
Target: FATTY-ACID-CoA LIGASE FADD28 (FATTY-ACID-CoA SYNTHETASE)
External Id: 2147-01_Inhibitor_SinglePoint_HTS_Activity
Name: Bursicon-induced LGR2 mediated cAMP production in LGR-2/CRE6x-Luciferase co-transfect...
Source: Broad Institute
Target: N/A
External Id: Bursicon-induced LGR2 mediated cAMP production in LGR-2/CRE6x-Luciferase co-transfected HEK293 cells Inhibition - 7011-01_Antagonist_SinglePoint_HTS_Activity
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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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