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Compound Summary

General Compound Information

Yohimbine

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Description

Yohimbine is an indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina. It has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. It derives from a yohimbic acid.

Synonyms

Yohimbine; Yohimbin; 146-48-5; Quebrachin; Quebrachine;

Corynine;APHRODINE;Yohimbic acid methyl ester;Aphrosol;(+)-Yohimbine;Johimbin;Actibine;Yohimbinum;17-Hydroxyyohimban-16-carboxylic acid methyl ester;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-;CHEMBL15245;2Y49VWD90Q;17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester;DTXSID9040130;CHEBI:10093;(16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester;methyl 17alpha-hydroxyyohimban-16alpha-carboxylate;methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate;YOHIMBINE CHLORIDE;DTXCID7020130;CHEMBL537669;Yohimbine (DCF);CAS-146-48-5;Amberlite CG 400;Amberlite CG-400;methyl hydroxy[?]carboxylate;EINECS 205-672-0;BRN 0097276;trans-Quinolizidine yohimbine;UNII-2Y49VWD90Q;Yohimbe bark;YOHIMBE HYDROCHLORIDE;CCRIS 9415;SR-01000075297;Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.;YohimbeHydrochloride;37247-87-3;NSC19509;YOHIMBINE [MI];Prestwick0_000584;Prestwick1_000584;Prestwick2_000584;Prestwick3_000584;Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester;YOHIMBINE [VANDF];YOHIMBINUM [HPUS];cid_6169;cid_8969;YOHIMBINE [WHO-DD];Lopac0_001210;SCHEMBL33954;BSPBio_000428;BSPBio_001236;GTPL102;KBioGR_000576;KBioSS_000576;4-25-00-01237 (Beilstein Handbook Reference);MLS000728591;SPBio_002647;BPBio1_000472;Yohimbol-16alpha-carboxylic acid, methyl ester (6CI);BCBcMAP01_000032;KBio2_000576;KBio2_003144;KBio2_005712;KBio3_001031;KBio3_001032;Bio1_000455;Bio1_000944;Bio1_001433;Bio2_000458;Bio2_000938;HMS1362N17;HMS1792N17;HMS1990N17;HMS2089G19;HMS2234C18;ZINC3860825;Tox21_110019;BDBM50013515;BDBM50203564;MFCD00005093;AKOS015902024;Tox21_110019_1;Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester;Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI);CCG-205284;CS-5173;DB01392;GS-5751;SDCCGSBI-0051177.P002;IDI1_002213;MRF-0000020;SMP1_000320;NCGC00013260-01;NCGC00025018-05;NCGC00025018-06;NCGC00025018-07;NCGC00025018-10;NCGC00025018-11;NCGC00025018-17;HY-12715;SMR000470778;17a-hydroxy-16a-methoxycarbonyl-yohimbane;C09256;D08685;H10057;EN300-19731915;Q412226;SR-01000075297-5;BRD-K35586044-001-02-6;BRD-K35586044-003-03-0;BRD-K35586044-003-11-3;17.ALPHA.-HYDROXY-20-.ALPHA.-YOHIMBAN-16-.BETA.-CARBOXYLIC ACID, METHYL ESTER;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)- (9CI);(1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester hydrochloride;103834-06-6;methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate;

FlavorDB ID

104 PUBCHEM ID

Molecular Weight

354.4 Molecular Formula

C21H26N2O3

Openeye Can Smiles

COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O

IUPAC Inchikey

BLGXFZZNTVWLAY-SCYLSFHTSA-N

Network

Similarity

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Yohimbine

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Reference point information of this compound is not available!

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

Reference value information of this compound is not available!

Genotoxicity

Author	YEAR	OUTPUT ID	Genotoxicity
EFSA ANS	2013	2326	No data

EFSA Outputs

Output ID	Title	DOI	Published
2326	Scientific Opinion on the evaluation of the safety in use of Yohimbe (Pausinystalia yohimbe (K. Schum.) Pierre ex Beille).	doi:10.2903/j.efsa.2013.3302	24Jul2013

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R1	details	Activated	300.00
TAS2R4	details	Activated	300.00
TAS2R10	details	Activated	300.00
TAS2R38	details	Activated	300.00
TAS2R46	details	Activated	300.00

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental LCMS	view	LCMS_Positive	positive

Content

Compound Summary

Yohimbine

Description

Yohimbine is an indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina. It has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. It derives from a yohimbic acid.

Synonyms

Yohimbine; Yohimbin; 146-48-5; Quebrachin; Quebrachine;

FlavorDB ID

104

PUBCHEM ID

8969

Molecular Weight

354.4

Molecular Formula

C21H26N2O3

Openeye Can Smiles

COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O

IUPAC Inchikey

BLGXFZZNTVWLAY-SCYLSFHTSA-N

Network

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Similarity

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Content

Compound Summary

Yohimbine

Description

Yohimbine is an indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina. It has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. It derives from a yohimbic acid.

Synonyms

Yohimbine; Yohimbin; 146-48-5; Quebrachin; Quebrachine;

FlavorDB ID

104

PUBCHEM ID

8969

Molecular Weight

354.4

Molecular Formula

C21H26N2O3

Openeye Can Smiles

COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O

IUPAC Inchikey

BLGXFZZNTVWLAY-SCYLSFHTSA-N

Network

Shown in network

Similarity

Show/Hide similarity panel

OpenFoodTox: component Yohimbine

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

GC-MS Spectrum