97-39-2

Hazards Identification

Pictogram(s):

Signal:

Danger

GHS Hazard Statements:

H301: Toxic if swallowed [Danger Acute toxicity, oral]
H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]
H373: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

Precautionary Statement Codes:

P203, P260, P264, P264+P265, P270, P280, P301+P316, P305+P351+P338, P308+P316, P318, P319, P321, P330, P337+P317, P405, and P501

Hazard Classes and Categories:

Acute toxicity (Oral) - Category 3
Serious eye damage/eye irritation - Category 2A
Reproductive toxicity - Category 2
Specific target organ toxicity - Single exposure - Category 1 (central nervous system)
Specific target organ toxicity - Repeated exposure - Category 2 (central nervous system)
Hazardous to the aquatic environment (Acute) - Category 2

Hazards Summary:

A selective ligand for the sigma site in the mammalian CNS--high parenteral doses in rodents cause behavioral effects; [Reference #1] Presumed to be irritating to eye mucous membranes; [HSDB] Oral LD50 (rat) = 500 mg/kg; Oral LDLo (unspecified mammal) = 120 mg/kg (Effects included somnolence, dyspnea, and cyanosis.) [ChemIDplus] An eye irritant; [eChemPortal: ERMA] May cause irritation; [MSDSonline]

Usage

Uses

Used in Pharmaceutical Industry:
Di-o-tolylguanidine is used as a selective ligand for the sigma-binding site due to its high binding affinity. This property makes it a valuable compound for the development of drugs targeting the sigma receptors, which are involved in various physiological processes and potential therapeutic applications.
Used in Research Applications:
Di-o-tolylguanidine is used as a research tool for studying the interaction between sigma receptors and dopamine drugs. This helps in understanding the role of sigma receptors in various neurological and psychiatric disorders, as well as their potential as targets for drug development.
Used in Drug Development:
Di-o-tolylguanidine is used as a lead compound in the development of new drugs targeting the sigma receptors. Its high binding affinity and selectivity make it a promising candidate for the creation of medications that can modulate the activity of these receptors for therapeutic purposes.

Flammability and Explosibility

Nonflammable

Biological Activity

Displays high and roughly equal affinity for both σ 1 and σ 2 receptors.

Safety Profile

Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

The guanidine crystallises from aqueous EtOH. The sulfate has m 253-254o(dec, H2O). [Beilstein 12 H 803, 12 II 445, 12 III 1871, 16 IV 1764]

References

1) Weber?et al.?(1986),?1,3-Di(2-[5-3H]tolyl)guanidine: a selective ligand that labels sigma-type receptors for psychotomimetic opiates and antipsychotic drugs; Proc. Natl. Acad. Sci. USA,?83?8784 2) Scherz?et al.?(1990),?Synthesis and Structure-Activity Relationships of N,N’-Di-o-tolylguanidine Analogues, High-Affinity Ligands for the Haloperidol-Sensitive σ Receptor; J. Med. Chem.,?33?2421

InChI:InChI=1/C15H17N3/c1-11-7-3-5-9-13(11)18(15(16)17)14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H3,16,17)

Upstream product

• 137-97-3 N,N'-di(o-tolyl)thiourea 
• 22695-18-7 N,N-di-o-tolylthiourea 
• 95-53-4 o-toluidine 
• 506-77-4 cyanogen chloride 
• 7664-41-7 ammonia 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 56-23-5 tetrachloromethane 
• 615-37-2 ortho-methylphenyl iodide 
• 124-46-9 guanidine hydrogen carbonate 
• 506-93-4 guanidine nitrate 
• 646-34-4 guanidinium sulfate 
• 95-46-5 2-methylphenyl bromide 
• 614-78-8 o-tolylthiourea 

Downstream Products

• 3354-37-8 4-phenyl-1,2-dithiole-3-thione 
• 94265-89-1 bis(1-methyl-1-phenylethyl)disulfide 
• 23356-34-5 1-formamidino-3-phenylthiourea 
• 16412-73-0 N-(N_.N'-Di-o-tolyl-carbamimidoyl)-N'-(tert-butyl)-thioharnstoff 
• 4132-53-0 4-(4-tert-butyl-phenyl)-[1,2]dithiol-3-thione 
• 7783-06-4 hydrogen sulfide 
• 3467-29-6 4-p-tolyl-1,2-dithiol-3-thione 
• 114841-66-6 4-(4-ethyl-phenyl)-[1,2]dithiol-3-thione 
• 1417202-95-9 2,3-di(p-anisyl)cyclopropenethione 
• 1417203-04-3 4,5-diferrocenyl-1-(o-tolyl)-2-(o-tolyl)imino-1,2-dihydropyrimidine 
• 1550369-69-1 1-(o-tolyl)-2-(o-tolylamino)-1H-benzo[d]imidazol-6-ol 
• 120-66-1 N-(2-methylphenyl)acetamide 

Relevant academic research and scientific papers

Synthesis of symmetrical and unsymmetrical N, N ′-diaryl guanidines via copper/N-methylglycine-catalyzed arylation of guanidine nitrate

CuI/N-methylglycine-catalyzed coupling reaction of guanidine nitrate with both aryl iodides and bromides takes place at 70-100 °C, affording symmetrical N,N′-diaryl guanidines with good to excellent yields. Unsymmetrical N,N′-diaryl guanidines can be assembled via monoarylation of guanidine nitrate with aryl iodides bearing a strong electron-withdrawing group and subsequent coupling with another aryl iodide.

Copper-catalyzed guanidinylation of aryl iodides: The formation of N,N′-disubstituted guanidines

Chemical Equation Presented A copper-catalyzed cross-coupling reaction of guanidine nitrate with aryl iodides was used for the formation of N,N′-disubstituted guanidines to be used as potential therapeutics for strokes. A relatively inexpensive commercially available guanidine salt and a series of aryl iodides together with copper iodide and N,N-diethylsalicylamide as an efficient catalyst/1 igand system provided a simple diarylation procedure.

Role of quaternaryammonium permanganates in the synthesis of substituted guanidines - A comparative study

Quaternaryammonium permanganate transforms 1,3-diarylthioureas in the presence of an amine to the respective trisubstituted guanidines in excellent yields.

A Short and Concise Synthesis of Guanidines

A facile high yielding process of guanidines is reported by reaction of amine nucleophiles on the oxidised thioureas in an aqueous medium using the unexploited reagents sodium chlorite and sodium metaperiodate for the oxidation of 1,3-disubstituted thioureas.

Lac sulfur on alumina-triethanolamine - An effective reagent for the synthesis of substituted guanidines

A direct synthesis of substituted guanidines is reported from their thiourea analogues. The strategy adopted is a concise approach to the synthesis of the title compounds.

Disturbance-of-consciousness improving agent

The present invention provides a disturbance-of-consciousness improving agent which is a highly effective and quick remedy and which can be administered orally. The disturbance-of-consciousness improving agent of the invention contains a sigma receptor agonist compound as an active ingredient.