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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:21 UTC
HMDB IDHMDB0015301
Secondary Accession Numbers
  • HMDB15301
Metabolite Identification
Common NameGuanethidine
DescriptionGuanethidine, also known as octadine or ismelin, belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. Guanethidine is a drug which is used for the treatment of moderate and severe hypertension, either alone or as an adjunct, and for the treatment of renal hypertension. Side effects include postural and exercise hypotension, sexual dysfunction (delayed or retrograde ejaculation), and diarrhea.Guanethidine is transported by uptake 1 into the presynaptic terminal transported by norepinephrine transporter (NET). Guanethidine is a very strong basic compound (based on its pKa). Guanethidine is transported across the sympathetic nerve membrane by the same mechanism that transports norepinephrine itself (NET, uptake 1), and uptake is essential for the drug's action. Spontaneous release is not affected.Guanethidine was once a mainstay for hypertension resistant to other agents, and was often used safely during pregnancy, but it is no longer used in the US due to lack of availability. Once inside the terminal it blocks the release of norepinephrine in response to arrival of an action potential. It becomes concentrated in norepinephrine transmitter vesicles, replacing norepinephrine in these vesicles. It is still licensed in some countries, e.g., UK, for the rapid control of blood pressure in a hypertensive emergency. It may also inhibit the release of granules by decreasing norepinephrine. Intravenous nerve block (Bier block) using guanethidine has been used to treat chronic pain caused by complex regional pain syndrome. Once guanethidine has entered the nerve, it is concentrated in transmitter vesicles, where it replaces norepinephrine. This leads to a gradual depletion of norepinephrine stores in the nerve endings. Guanethidine is an antihypertensive drug that reduces the release of catecholamines, such as norepinephrine.
Structure
Data?1582753281
Synonyms
ValueSource
(2-(Octahydro-1-azocinyl)ethyl)guanidineChEBI
2-(1'-Azacyclooctyl)ethylguanidineChEBI
2-(1-N,N-Heptamethyleneimino)ethylguanidineChEBI
GuanethidinumChEBI
GuanetidinaChEBI
N-(2-Perhydroazocin-1-ylethyl)guanidineChEBI
Guanethidine monosulfateHMDB
Guanethidine monosulphateHMDB
Guanethidine sulphaeHMDB
Guanethidine sulfate (1:1)HMDB
Guanethidine sulfate (2:1), 14C-labeledHMDB
OctadineHMDB
OktadinHMDB
monoSulfate, guanethidineHMDB
Guanethidine sulfateHMDB
Guanethidine sulfate (1:2)HMDB
Guanethidine sulfate (2:1)HMDB
IsmelinHMDB
IsobarinHMDB
((2-Hexahydro-1(2H)-azocinyl)ethyl)guanidineHMDB
Sulfate, guanethidineHMDB
Chemical FormulaC10H22N4
Average Molecular Weight198.3085
Monoisotopic Molecular Weight198.184446724
IUPAC Name2-[2-(azocan-1-yl)ethyl]guanidine
Traditional Nameismelin
CAS Registry Number645-43-2
SMILES
NC(N)=NCCN1CCCCCCC1
InChI Identifier
InChI=1S/C10H22N4/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14/h1-9H2,(H4,11,12,13)
InChI KeyACGDKVXYNVEAGU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentGuanidines
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • Guanidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point250 °C (sulfate salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility2.25 g/LNot Available
LogP0.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available144.236http://allccs.zhulab.cn/database/detail?ID=AllCCS00000703
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.25 g/LALOGPS
logP10(0.89) g/LALOGPS
logP10(0.74) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Basic)11.77ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.64 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.7 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.61731661259
DarkChem[M-H]-142.6831661259
DeepCCS[M+H]+151.80430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GuanethidineNC(N)=NCCN1CCCCCCC12786.6Standard polar33892256
GuanethidineNC(N)=NCCN1CCCCCCC11675.9Standard non polar33892256
GuanethidineNC(N)=NCCN1CCCCCCC11949.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Guanethidine,1TMS,isomer #1C[Si](C)(C)NC(N)=NCCN1CCCCCCC12056.5Semi standard non polar33892256
Guanethidine,1TMS,isomer #1C[Si](C)(C)NC(N)=NCCN1CCCCCCC11849.1Standard non polar33892256
Guanethidine,1TMS,isomer #1C[Si](C)(C)NC(N)=NCCN1CCCCCCC13375.7Standard polar33892256
Guanethidine,2TMS,isomer #1C[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C2184.8Semi standard non polar33892256
Guanethidine,2TMS,isomer #1C[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C1924.0Standard non polar33892256
Guanethidine,2TMS,isomer #1C[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C3422.7Standard polar33892256
Guanethidine,2TMS,isomer #2C[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C2126.8Semi standard non polar33892256
Guanethidine,2TMS,isomer #2C[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C2034.6Standard non polar33892256
Guanethidine,2TMS,isomer #2C[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C3393.8Standard polar33892256
Guanethidine,3TMS,isomer #1C[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C2181.3Semi standard non polar33892256
Guanethidine,3TMS,isomer #1C[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C2123.3Standard non polar33892256
Guanethidine,3TMS,isomer #1C[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C3171.5Standard polar33892256
Guanethidine,4TMS,isomer #1C[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2256.9Semi standard non polar33892256
Guanethidine,4TMS,isomer #1C[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2298.5Standard non polar33892256
Guanethidine,4TMS,isomer #1C[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2837.1Standard polar33892256
Guanethidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NCCN1CCCCCCC12245.8Semi standard non polar33892256
Guanethidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NCCN1CCCCCCC12051.8Standard non polar33892256
Guanethidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NCCN1CCCCCCC13538.6Standard polar33892256
Guanethidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C(C)(C)C2568.1Semi standard non polar33892256
Guanethidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C(C)(C)C2351.6Standard non polar33892256
Guanethidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C(C)(C)C3462.3Standard polar33892256
Guanethidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C(C)(C)C2491.7Semi standard non polar33892256
Guanethidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C(C)(C)C2433.3Standard non polar33892256
Guanethidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C(C)(C)C3567.9Standard polar33892256
Guanethidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2765.8Semi standard non polar33892256
Guanethidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2730.3Standard non polar33892256
Guanethidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3231.1Standard polar33892256
Guanethidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3046.5Semi standard non polar33892256
Guanethidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3049.6Standard non polar33892256
Guanethidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3035.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Guanethidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dl-9800000000-92577f077502658eda152017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanethidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOFsplash10-0002-0900000000-63bf143534cccc53e0992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOFsplash10-000g-3900000000-b0c1213301460e6159e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOFsplash10-000f-8900000000-a1d8b2ab68936ac02c482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOFsplash10-007c-9200000000-091425f6c0c880a5afdd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOFsplash10-0a4r-9000000000-3d40142c51842fbbf5fc2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 10V, Positive-QTOFsplash10-0002-2900000000-3c0d9ad535e10192de332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 20V, Positive-QTOFsplash10-01pc-9800000000-f1d0a92cd4e7f5d5da782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 40V, Positive-QTOFsplash10-03di-9200000000-7f351fa76ffff520f4072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 10V, Negative-QTOFsplash10-0a4j-2900000000-85cc5b54f54b4d66b7d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 20V, Negative-QTOFsplash10-0a4i-2900000000-5456c549767554136a2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 40V, Negative-QTOFsplash10-052f-9100000000-72d038e0b4bab69767222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 10V, Positive-QTOFsplash10-0002-0900000000-ef3ffa4801d71aa440932021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 20V, Positive-QTOFsplash10-0006-2900000000-71e448522ec8b2788ede2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 40V, Positive-QTOFsplash10-03dl-6900000000-7f013e5325db2e1461742021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 10V, Negative-QTOFsplash10-0udj-0900000000-364208ae432e6172afa52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 20V, Negative-QTOFsplash10-0udi-0900000000-661b5d94a8a02cdcfc2a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanethidine 40V, Negative-QTOFsplash10-006x-4900000000-936412e2b075cbd2a91e2021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart 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 DB01170 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01170 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01170
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3398
KEGG Compound IDC07036
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanethidine
METLIN IDNot Available
PubChem Compound3518
PDB IDNot Available
ChEBI ID5557
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 monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Joyce PI, Atcheson R, Marcus RJ, Heffernan AM, Rowbotham DJ, Lambert DG: Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells. Neurosci Lett. 2001 Jun 15;305(3):161-4. [PubMed:11403930 ]
  2. Yi E, Love JA: Alpha-adrenergic modulation of synaptic transmission in rabbit pancreatic ganglia. Auton Neurosci. 2005 Oct 30;122(1-2):45-57. Epub 2005 Aug 25. [PubMed:16126010 ]
  3. Galli A, Blakely RD, DeFelice LJ: Norepinephrine transporters have channel modes of conduction. Proc Natl Acad Sci U S A. 1996 Aug 6;93(16):8671-6. [PubMed:8710929 ]