Guanethidine (CED0004575)

Record Information

Version

1.0

Creation Date

2016-05-25 18:25:42 UTC

Update Date

2026-08-18 03:14:38 UTC

Accession Number

CHEM022253

Identification

Common Name

Guanethidine

Class

Small Molecule

Description

Guanethidine is an organic compound with the chemical formula C10H22N4 and an average molecular weight of 198.31 g/mol. Guanethidine belongs to the guanidines, a subclass of organonitrogen compounds within the organic compounds. In terms of biological activity, it is recorded as an inducer of the protein target Sodium-dependent noradrenaline transporter (SLC6A2). The compound is found in or released from seven recorded sources across various sectors. Within healthcare, pharmaceuticals, and veterinary products, it is used in antihypertensives as well as miotics and antiglaucoma preparations. It is also associated with household cleaning and consumer products, specifically tobacco smoke filters. Additionally, it is found in electrical and electronic equipment, including electrodes, antennas, conductive bodies characterized by their conductive materials, and electrically stimulated smoking devices. The recorded exposure route for this substance is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2-(Octahydro-1-azocinyl)ethyl)guanidine	ChEBI
2-(1'-Azacyclooctyl)ethylguanidine	ChEBI
2-(1-N,N-Heptamethyleneimino)ethylguanidine	ChEBI
Guanethidinum	ChEBI
Guanetidina	ChEBI
N-(2-Perhydroazocin-1-ylethyl)guanidine	ChEBI
Guanethidine monosulfate	HMDB
Guanethidine monosulphate	HMDB
Guanethidine sulphae	HMDB
Guanethidine sulfate (1:1)	HMDB
Guanethidine sulfate (2:1), 14C-labeled	HMDB
Octadine	HMDB
Oktadin	HMDB
monoSulfate, guanethidine	HMDB
Guanethidine sulfate	HMDB
Guanethidine sulfate (1:2)	HMDB
Guanethidine sulfate (2:1)	HMDB
Ismelin	HMDB
Isobarin	HMDB
((2-Hexahydro-1(2H)-azocinyl)ethyl)guanidine	HMDB
Sulfate, guanethidine	HMDB

Chemical Formula

C₁₀H₂₂N₄

Average Molecular Mass

198.309 g/mol

Monoisotopic Mass

198.184 g/mol

CAS Registry Number

645-43-2

IUPAC Name

2-[2-(azocan-1-yl)ethyl]guanidine

Traditional Name

ismelin

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 Key

ACGDKVXYNVEAGU-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Guanidines

Direct Parent

Guanidines

Alternative Parents

Substituents

Tertiary aliphatic amine
Tertiary amine
Guanidine
Azacycle
Organoheterocyclic compound
Carboximidamide
Organopnictogen compound
Hydrocarbon derivative
Imine
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

guanidines (CHEBI:5557 )
azocanes (CHEBI:5557 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	2.25 g/L	ALOGPS
logP	0.89	ALOGPS
logP	0.74	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	11.77	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.64 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.7 m³·mol⁻¹	ChemAxon
Polarizability	23.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-05dl-9800000000-92577f077502658eda15	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-63bf143534cccc53e099	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000g-3900000000-b0c1213301460e6159e2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000f-8900000000-a1d8b2ab68936ac02c48	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-007c-9200000000-091425f6c0c880a5afdd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4r-9000000000-3d40142c51842fbbf5fc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-2900000000-3c0d9ad535e10192de33	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01pc-9800000000-f1d0a92cd4e7f5d5da78	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-9200000000-7f351fa76ffff520f407	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4j-2900000000-85cc5b54f54b4d66b7d7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2900000000-5456c549767554136a2a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9100000000-72d038e0b4bab6976722	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-ef3ffa4801d71aa44093	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2900000000-71e448522ec8b2788ede	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-6900000000-7f013e5325db2e146174	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udj-0900000000-364208ae432e6172afa5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0900000000-661b5d94a8a02cdcfc2a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-4900000000-936412e2b075cbd2a91e	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
862.0	Log mg/kg	[480:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
289	Antihypertensives	Healthcare, pharmaceuticals & veterinary products	Not Available
398	Antiglaucoma preparations and miotics	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
603	Nematocides	Agriculture & land management	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

2 pathways

Guanethidine Drug Metabolism

Guanethidine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	434.554
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	964.396
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	530.231
Click to view 3D structure	Histamine H3 receptor	Q9QYN8	Rattus norvegicus	Predicted (SEA)	168.933
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	1168.13
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	510.224
Click to view 3D structure	Transient receptor potential cation channel subfamily V member 3	Q8K424	Mus musculus	Predicted (SEA)	96.9223
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	2247.35
Click to view 3D structure	Sigma intracellular receptor 2	Q5U3Y7	Rattus norvegicus	Predicted (SEA)	571.18
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	4292.37
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	2874.82
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	1113.48
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	1346.64
Click to view 3D structure	Cholinesterase	P81908	Equus caballus	Predicted (SEA)	1162.44
Click to view 3D structure	Histamine H4 receptor	Q9H3N8	Humans	Predicted (SEA)	709.44
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	3174.85
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	2151.99
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	2464.01
Click to view 3D structure	Histamine H1 receptor	P31389	Cavia porcellus	Predicted (SEA)	750.233
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	2399.08
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	2374.79
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	3211.36
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	2697.16
Click to view 3D structure	Histamine H3 receptor	Q9JI35	Cavia porcellus	Predicted (SEA)	498.78
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	3637.43