Yohimbine hydrochloride - 10mM in DMSO , CAS No.65-19-0

CAS: 65-19-0 Cat. No.: Y425298 Molecular Weight: 390.9 Beilstein Registry Number: 25(2)204 EC Number: 200-600-4 PubChem CID: 6169

GRADE & PURITY 10mM in DMSO

Synonyms

NCGC00094457-01 | Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16alpha,17alpha)- | Yohimbin hydrochloride [USP] | Yohimbine hydrochloride [USP:BAN] | Yocon | Yohimbe | 17?-Hydroxyyohimban-16?-carboxylic acid methyl ester hyd

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Yohimbine hydrochloride is an α2-adrenoceptor antagonist (pKi values are 8.52, 8.00 and 9.17 for human α2A, α2B and α2C receptors respectively). Yohimbine hydrochloride is an inhibitor of alpha2A-AR, alpha2B-AR and alpha2C-AR.
An α2-adrenoceptor antagonist

Specifications

Synonyms

NCGC00094457-01 | Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16alpha, 17alpha)- | Yohimbin hydrochloride [USP] | Yohimbine hydrochloride [USP:BAN] | Yocon | Yohimbe | 17?-Hydroxyyohimban-16?-carboxylic acid methyl ester hyd

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Selective α 2 adrenoceptor antagonist (pK i values are 8.52, 8.00 and 9.17 for human α 2A , α 2B and α 2C receptors, respectively).

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl
• IUPAC Name: methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride
• InChIKey: PIPZGJSEDRMUAW-VJDCAHTMSA-N
• INCHI: 1S/C21H26N2O3.ClH/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;1H/t12-,15-,17-,18-,19+;/m0./s1
• Isomeric SMILES: COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl
• WGK Germany: 3
• RTECS: ZG1015000
• PubChem CID: 6169
• UN Number: 1544
• Molecular Weight: 390.9
• Beilstein: 25(2)204
• Reaxy-Rn: 4303497

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Yohimbine alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Yohimbine alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Yohimbine alkaloids
• Alternative Parents: Corynanthean-type alkaloids Beta carbolines 3-alkylindoles Aralkylamines Beta hydroxy acids and derivatives Benzenoids Piperidines Pyrroles Heteroaromatic compounds Methyl esters Amino acids and derivatives Cyclic alcohols and derivatives Trialkylamines Secondary alcohols Monocarboxylic acids and derivatives Azacyclic compounds Carbonyl compounds Organic oxides Organopnictogen compounds Hydrocarbon derivatives Hydrochlorides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Yohimbine - Corynanthean skeleton - Yohimbine alkaloid - Beta-carboline - Pyridoindole - 3-alkylindole - Indole - Indole or derivatives - Beta-hydroxy acid - Aralkylamine - Hydroxy acid - Piperidine - Benzenoid - Cyclic alcohol - Heteroaromatic compound - Pyrrole - Methyl ester - Secondary alcohol - Amino acid or derivatives - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid ester - Organoheterocyclic compound - Azacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrochloride - Organic oxide - Alcohol - Organopnictogen compound - Hydrocarbon derivative - Amine - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

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ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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KCNH2 Tclin HERG (29587 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

Discover Target: THRB

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

Discover Target: KDM4A

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

Discover Target: PMP22

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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Associated Targets(non-human)

Saccharomyces cerevisiae (19171 Activities)

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Plasmodium falciparum (966862 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light sensitive
• Specific Rotation[α]: 103° (C=1,H2O)
• Melt Point(°C): 285-288°C
• Molecular Weight: 390.900 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 390.171 Da
• Monoisotopic Mass: 390.171 Da
• Topological Polar Surface Area: 65.600 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 555.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Ning Wang, Yue-Wu Xie, Meng-Yu Li, Fei-Fei Li, Li-Yuan Zhang, Yu-Lin You, Shu-Qi Wang.  (2021)  Simultaneous determination of five alkaloids from Rauvolfia vomitoria in rat plasma by LC-MS/MS: Application to a comparative pharmacokinetic study in normal and type 2 diabetic rats.  JOURNAL OF SEPARATION SCIENCE,  44  (7): (1391-1403).  [PMID:33470534] [10.1002/jssc.202000914]

2. Zhi Liu, Hai-Long Wu, Yong Li, Hui-Wen Gu, Xiao-Li Yin, Li-Xia Xie, Ru-Qin Yu.  (2015)  Rapid and simultaneous determination of five vinca alkaloids in Catharanthus roseus and human serum using trilinear component modeling of liquid chromatography–diode array detection data.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:26321366] [10.1016/j.jchromb.2015.08.008]

3. Dongmei Cui, Li Mi, Xuan Xu, Jusheng Lu, Jing Qian, Songqin Liu.  (2014)  Nanocomposites of Graphene and Cytochrome P450 2D6 Isozyme for Electrochemical-Driven Tramadol Metabolism.  LANGMUIR,      [PMID:25222611] [10.1021/la502699m]

4. Zhiqin Liu, Yufeng Xu, Wei Liu, Lin Wang, Zhen Dong, Jianguo Zeng.  (2025)  Macleaya cordata protopine total alkaloids as potential treatment for diarrhoea: Mechanistic insights and target identification.  RESEARCH IN VETERINARY SCIENCE,      [PMID:40184723] [10.1016/j.rvsc.2025.105633]

5. Shiyan Liu, Xuefeng Zhang, Xin Gong, Jinxin Yu, Tao Lin, Qian Xiang, Xinnian Zeng, Jiali Liu.  (2025)  molecular and pharmacological characterization of the dopamine receptors in the oriental fruit fly, Bactrocera dorsalis.  INSECT BIOCHEMISTRY AND MOLECULAR BIOLOGY,      [PMID:40245998] [10.1016/j.ibmb.2025.104312]

6. Yanan Li, Hua Zheng, Lei Xu, Linfeng Chen, Fan Xia, Yanlin Song.  (2025)  A Biomimetic Nanofluidic Tongue for Highly Selective and Sensitive Bitter Perception.  Journal of Materials Chemistry A,      [PMID:] [10.1039/D5TA02127H]

7. Li Xiao, Lin Lizhou, Zhu Mingrui, Li Xiaolong, Yu Jifeng, Lu Dan, Li Shaoyue, Shen Yuting, Xiong Bing, Zhao Chongke, Zhou Boyang, Yin Haohao, Xu Huixiong, Guan Xin.  (2026)  Low-intensity focused ultrasound-activated piezoelectric gel bandage for diabetic wound repair and neuropathic pain relief.  Nature Communications,      [PMID:41857055] [10.1038/s41467-026-70771-y]