15784-82-4

Basic information

• Product Name: 1-ADAMANTYLCYANAMIDE
• Synonyms: 1-ADAMANTYLCYANAMIDE;AKOS BC-0497;cyanamide, N-tricyclo[3.3.1.1~3,7~]dec-1-yl-
• CAS NO: 15784-82-4
• Molecular Formula: C₁₁H₁₆N₂
• Molecular Weight: 176.26
• Product Categories: Adamantane derivatives
• Mol File: 15784-82-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-ADAMANTYLCYANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ADAMANTYLCYANAMIDE(15784-82-4)
• EPA Substance Registry System: 1-ADAMANTYLCYANAMIDE(15784-82-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 15784-82-4(Hazardous Substances Data)

Usage

Type of compound

Cyanamide derivative

Composition

Adamantyl group and cyano group connected by an amine linker

Usage

Building block in organic synthesis and medicinal chemistry

Potential applications

Precursor for the synthesis of other organic compounds, pharmacological properties, antiviral agent, and ligand in catalytic reactions

Adamantyl group

A saturated hydrocarbon group consisting of a diamondoid structure of carbon atoms

Cyano group

A cyanide group (CN) bonded to a carbon atom

Amine linker

A nitrogen atom bonded to two carbon atoms via single bonds

Organic synthesis

The process of chemically synthesizing organic compounds

Medicinal chemistry

The study of the chemistry and biochemistry of drugs

Pharmacological properties

The actions and effects of a drug on the body

Antiviral agent

A substance that is used to treat viral infections

Catalytic reactions

Reactions that are sped up by the presence of a catalyst or a substance that increases the rate of a reaction without being consumed in the process.

Upstream product

• 506-68-3 bromocyane 
• 768-94-5 1-Adamantanamine 
• 3405-48-9 N-(1-adamantyl)formamide 
• 22110-53-8 1-adamantyl isocyanide 
• 50987-38-7 1-((3s,5s,7s)-adamantan-1-yl)-1H-tetrazole 

Downstream Products

• 124190-31-4 N-(2-methylphenyl)-N'-(adamantan-1-yl)guanidine 
• 133985-78-1 N-Adamantan-1-yl-N'-(4-fluoro-phenyl)-guanidine 
• 133985-82-7 N-Adamantan-1-yl-N'-(4-hydroxy-2-methyl-phenyl)-guanidine 
• 133985-72-5 N-Adamantan-1-yl-N'-(2-methoxy-phenyl)-guanidine 
• 133985-75-8 N-Adamantan-1-yl-N'-(4-methoxy-2-methyl-phenyl)-guanidine 
• 133985-74-7 N-Adamantan-1-yl-N'-(4-methoxy-phenyl)-guanidine 
• 133985-84-9 N-Adamantan-1-yl-N'-(3-iodo-phenyl)-guanidine 
• 133985-85-0 [125I]-PIPAG 
• 23166-33-8 N-(adamantan-1-yl)-N'-cyclohexyl-guanidine hydrochloride 
• 13072-69-0 1-(carbamoylamino)adamantne 
• 133985-79-2 N-Adamantan-1-yl-N'-(4-fluoro-2-methyl-phenyl)-guanidine 
• 133985-76-9 N-Adamantan-1-yl-N'-(2-fluoro-phenyl)-guanidine 
• 128413-79-6 N-Adamantan-1-yl-N'-[2-((E)-2-pentafluorophenyl-vinyl)-phenyl]-guanidine 
• 128413-82-1 N-Adamantan-1-yl-N'-[2-((E)-styryl)-phenyl]-guanidine 

Relevant articles and documents

Comparison of the Pharmacological Activity and Safety of 1-Adamantylguanidine and 3,5-Dimethyl-1-Adamantylguanidine to those of Memantine

Guanidine-containing analogs of amantadine and memantine, including 1-adamantylguanidine hydrochloride (IEM-2151) and 3,5-dimethyl-1-adamantylguanidine hydrochloride (IEM-2163), were synthesized and studied. IEM-2151 and IEM-2163 had greater antihypoxic, anticonvulsant, and neuroprotective activity than memantine; exhibited equally potent antiparkinsonian, antidepressant, and analgesic activity with memantine; and had higher therapeutic indices than memantine.

Cyanide-Free Synthesis of Air Stable N-Substituted Li and K Cyanamide Salts from Tetrazoles. Applications toward the Synthesis of Primary and Secondary Cyanamides as Precursors to Amidines

A practical two-step synthesis of N,N′-disubstituted cyanamides consists in the low-temperature metalation of N-substituted 5H-tetrazoles that undergo spontaneous cycloreversion at 0 °C releasing dinitrogen, and forming N-metalated cyanamides that can be reacted in situ with a variety of electrophiles. Remarkably, the N-substituted Li and K cyanamides are air stable white solids at room temperature. Addition of lithium organometallics to the N,N′-disubstituted cyanamides provides a new method for accessing N,N′-disubstituted amidines.

Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides

The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.

SUBSTITUTED GUANIDINES HAVING HIGH BINDING TO THE SIGMA RECEPTOR AND THE USE THEREOF

The invention relates to a method for the treatment or prophylaxis of psychosis, depression, hypertension, or anxiety in an animal by administering an effective amount of an N,N'-disubstituted guanidine or 2-iminoimadazolidine having an affinity for the s