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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:08 UTC
HMDB IDHMDB0014362
Secondary Accession Numbers
  • HMDB14362
Metabolite Identification
Common NameBethanidine
DescriptionBethanidine is only found in individuals that have used or taken this drug. It is a guanidinium antihypertensive agent that acts by blocking adrenergic transmission.Bethanidine, a guanidine derivative, is a peripherally acting antiadrenergic agent which primarily acts as an alpha2a adrenergic agonist. Bethanidine effectively decreases blood pressure by suppressing renin secretion or interfering with function of the sympathetic nervous system.
Structure
Data?1676999888
Synonyms
ValueSource
BetanidinaChEBI
BetanidineChEBI
BetanidinumChEBI
N,N'-dimethyl-n''-(phenylmethyl)-guanidineChEBI
Bethanidine sulfateHMDB
Bethanidine sulphateHMDB
BatelHMDB
Sulfate, bethanidineHMDB
Bethanidine, sulfate (2:1)HMDB
Wellcome brand OF betanidine sulfateHMDB
Chemical FormulaC10H15N3
Average Molecular Weight177.2462
Monoisotopic Molecular Weight177.126597495
IUPAC Name(E)-3-benzyl-1,2-dimethylguanidine
Traditional Namebethanidine
CAS Registry Number55-73-2
SMILES
CN\C(NCC1=CC=CC=C1)=N/C
InChI Identifier
InChI=1S/C10H15N3/c1-11-10(12-2)13-8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3,(H2,11,12,13)
InChI KeyNIVZHWNOUVJHKV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.58 g/LNot Available
LogP0.49Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP1.41ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)12.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.42 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.5 m³·mol⁻¹ChemAxon
Polarizability20.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.96831661259
DarkChem[M-H]-137.46631661259
DeepCCS[M+H]+140.08130932474
DeepCCS[M-H]-137.68630932474
DeepCCS[M-2H]-173.31830932474
DeepCCS[M+Na]+148.5830932474
AllCCS[M+H]+140.032859911
AllCCS[M+H-H2O]+135.832859911
AllCCS[M+NH4]+143.932859911
AllCCS[M+Na]+145.032859911
AllCCS[M-H]-142.632859911
AllCCS[M+Na-2H]-143.632859911
AllCCS[M+HCOO]-144.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BethanidineCN\C(NCC1=CC=CC=C1)=N/C2427.8Standard polar33892256
BethanidineCN\C(NCC1=CC=CC=C1)=N/C1586.0Standard non polar33892256
BethanidineCN\C(NCC1=CC=CC=C1)=N/C1663.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bethanidine,1TMS,isomer #1C/N=C(/NCC1=CC=CC=C1)N(C)[Si](C)(C)C1787.1Semi standard non polar33892256
Bethanidine,1TMS,isomer #1C/N=C(/NCC1=CC=CC=C1)N(C)[Si](C)(C)C1609.6Standard non polar33892256
Bethanidine,1TMS,isomer #1C/N=C(/NCC1=CC=CC=C1)N(C)[Si](C)(C)C2382.9Standard polar33892256
Bethanidine,1TMS,isomer #2C/N=C(\NC)N(CC1=CC=CC=C1)[Si](C)(C)C1705.2Semi standard non polar33892256
Bethanidine,1TMS,isomer #2C/N=C(\NC)N(CC1=CC=CC=C1)[Si](C)(C)C1564.9Standard non polar33892256
Bethanidine,1TMS,isomer #2C/N=C(\NC)N(CC1=CC=CC=C1)[Si](C)(C)C2391.1Standard polar33892256
Bethanidine,2TMS,isomer #1C/N=C(\N(C)[Si](C)(C)C)N(CC1=CC=CC=C1)[Si](C)(C)C1715.1Semi standard non polar33892256
Bethanidine,2TMS,isomer #1C/N=C(\N(C)[Si](C)(C)C)N(CC1=CC=CC=C1)[Si](C)(C)C1727.7Standard non polar33892256
Bethanidine,2TMS,isomer #1C/N=C(\N(C)[Si](C)(C)C)N(CC1=CC=CC=C1)[Si](C)(C)C2156.2Standard polar33892256
Bethanidine,1TBDMS,isomer #1C/N=C(/NCC1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C1942.2Semi standard non polar33892256
Bethanidine,1TBDMS,isomer #1C/N=C(/NCC1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C1832.4Standard non polar33892256
Bethanidine,1TBDMS,isomer #1C/N=C(/NCC1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C2490.7Standard polar33892256
Bethanidine,1TBDMS,isomer #2C/N=C(\NC)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C1889.5Semi standard non polar33892256
Bethanidine,1TBDMS,isomer #2C/N=C(\NC)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C1767.7Standard non polar33892256
Bethanidine,1TBDMS,isomer #2C/N=C(\NC)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2494.0Standard polar33892256
Bethanidine,2TBDMS,isomer #1C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2150.9Semi standard non polar33892256
Bethanidine,2TBDMS,isomer #1C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2102.6Standard non polar33892256
Bethanidine,2TBDMS,isomer #1C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2374.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bethanidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-b32a080ebd20af65e7e42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bethanidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bethanidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 10V, Positive-QTOFsplash10-004i-2900000000-e824de21a598fe2c16c02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 20V, Positive-QTOFsplash10-0006-9300000000-8faaf65b0ff1118abd172016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 40V, Positive-QTOFsplash10-0006-9000000000-b3000d31dfea6a9f7ff42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 10V, Negative-QTOFsplash10-004i-5900000000-34c95ebed4254861ff0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 20V, Negative-QTOFsplash10-002r-9700000000-9b98cfd13440f08568562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 40V, Negative-QTOFsplash10-05fr-9000000000-12a4a55f434814d511152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 10V, Negative-QTOFsplash10-004i-0900000000-73dee90f2774521acc832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 20V, Negative-QTOFsplash10-056r-9300000000-89259c73af7e3cca699d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 40V, Negative-QTOFsplash10-05fr-9700000000-adf98faa8ba1a2b731712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 10V, Positive-QTOFsplash10-004l-6900000000-c85c19d594809e4353a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 20V, Positive-QTOFsplash10-0006-9300000000-aad4cdd32404fd265e092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanidine 40V, Positive-QTOFsplash10-0006-9000000000-84735ad9e864b6773d542021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00217 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00217 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00217
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2278
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBethanidine
METLIN IDNot Available
PubChem Compound2368
PDB IDNot Available
ChEBI ID37937
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in inward rectifier potassium channel activity
Specific function:
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:
KCNJ1
Uniprot ID:
P48048
Molecular weight:
44794.6
References
  1. Bkaily G, Caille JP, Payet MD, Peyrow M, Sauve R, Renaud JF, Sperelakis N: Bethanidine increases one type of potassium current and relaxes aortic muscle. Can J Physiol Pharmacol. 1988 Jun;66(6):731-6. [PubMed:3167688 ]
  2. Bkaily G: Bethanidine, nitroprusside and atrial natriuretic factor open a cGMP-sensitive K+ channel in aortic muscle. Prog Clin Biol Res. 1990;327:507-15. [PubMed:2157221 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins
Gene Name:
ADRA2C
Uniprot ID:
P18825
Molecular weight:
49521.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Noshiro T, Miura Y, Kimura S, Meguro Y, Sugawara T, Ohashi H, Takahashi M, Sano N, Watanabe H, Ohzeki T, et al.: Functional relationships between platelet alpha 2-adrenoceptors and sympathetic nerve activity in clinical hypertensive states. J Hypertens. 1990 Dec;8(12):1097-104. [PubMed:1962798 ]
  4. Noshiro T, Miura Y, Kimura S, Meguro Y, Sugawara T, Ohashi H, Takahashi M, Sano N, Watanabe H, Ohzeki T, et al.: Functional relationship between platelet alpha 2-adrenoceptors and sympathetic nerve activity in man. Clin Exp Hypertens A. 1989;11 Suppl 1:287-94. [PubMed:2545383 ]