ContaminantDB: Yohimbine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:26:07 UTC

Update Date

2026-04-13 20:51:31 UTC

Accession Number

CHEM017527

Identification

Common Name

Yohimbine

Class

Small Molecule

Description

A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Yohimbine	ChEBI
(16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylic acid methyl ester	ChEBI
17alpha-Hydroxyyohimban-16alpha-carboxylic acid methyl ester	ChEBI
Aphrodine	ChEBI
Corynine	ChEBI
Johimbin	ChEBI
Quebrachin	ChEBI
Quebrachine	ChEBI
Yohimbic acid methyl ester	ChEBI
Yohimbin	ChEBI
(16a,17a)-17-Hydroxyyohimban-16-carboxylate methyl ester	Generator
(16a,17a)-17-Hydroxyyohimban-16-carboxylic acid methyl ester	Generator
(16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylate methyl ester	Generator
(16Α,17α)-17-hydroxyyohimban-16-carboxylate methyl ester	Generator
(16Α,17α)-17-hydroxyyohimban-16-carboxylic acid methyl ester	Generator
17a-Hydroxyyohimban-16a-carboxylate methyl ester	Generator
17a-Hydroxyyohimban-16a-carboxylic acid methyl ester	Generator
17alpha-Hydroxyyohimban-16alpha-carboxylate methyl ester	Generator
17Α-hydroxyyohimban-16α-carboxylate methyl ester	Generator
17Α-hydroxyyohimban-16α-carboxylic acid methyl ester	Generator
Yohimbate methyl ester	Generator
Aphrodyne	HMDB
Aventis brand OF yohimbine hydrochloride	HMDB
Solvay brand OF yohimbine hydrochloride	HMDB
Yohimbine hydrochloride	HMDB
Aphrodine hydrochloride	HMDB
Hydrochloride, yohimbine	HMDB
Pluriviron	HMDB
Rauwolscine	HMDB
Palisades brand OF yohimbine hydrochloride	HMDB
Star brand OF yohimbine hydrochloride	HMDB
StegroPharm brand OF yohimbine hydrochloride	HMDB
Tartrate, corynanthine	HMDB
Corynanthine	HMDB
Corynanthine tartrate	HMDB
Glenwood brand OF yohimbine hydrochloride	HMDB
Hydrochloride, aphrodine	HMDB
Kramer brand OF yohimbine hydrochloride	HMDB
Rauhimbine	HMDB
Yocon	HMDB
Yohimbin spiegel	HMDB
Yohimbine houdé	HMDB
Yohimex	HMDB

Chemical Formula

C₂₁H₂₆N₂O₃

Average Molecular Mass

354.443 g/mol

Monoisotopic Mass

354.194 g/mol

CAS Registry Number

146-48-5

IUPAC Name

methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional Name

yohimbine

SMILES

[H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

InChI Identifier

InChI=1S/C21H26N2O3/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/t12-,15-,17-,18-,19+/m0/s1

InChI Key

BLGXFZZNTVWLAY-SCYLSFHTSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Yohimbine
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Beta-hydroxy acid
Hydroxy acid
Benzenoid
Piperidine
Heteroaromatic compound
Methyl ester
Cyclic alcohol
Pyrrole
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Tertiary amine
Secondary alcohol
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Carbonyl group
Organic oxygen compound
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl 17-hydroxy-20xi-yohimban-16-carboxylate (CHEBI:10093 )
Indole alkaloids (C09256 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	7.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.63 m³·mol⁻¹	ChemAxon
Polarizability	40.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-008i-0396000000-43448cca1e1ad4343ac0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00xs-2139200000-8288a21cfcdae82fc694	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-3921000000-e28dd8692e2b8dd63330	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0019000000-98fd50566f845231fbed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0129000000-49a3b77851cb2f327e51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ffx-0891000000-1297a98bf2d980f32361	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-6448f2e7be3b7fa35128	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-a436855e9ddc5d8e061e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-07ef-3956000000-386e3fa9fb16f1a30cf6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-b3d998cb3c47c9700660	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0009000000-42b2cee0514145bdbc16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002g-0695000000-7eacdb4b3fbff0521dcd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-1bc1d16b561be98b6dbc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0095000000-d9723526ae361fda41c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f96-0192000000-a13fb9eefdc725558673	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01392

HMDB ID

HMDB0015464

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001789

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Yohimbine (CHEM017527)

Structure for CHEM017527: Yohimbine