CYCLOHEXYLAMINE

CYCLOHEXYLAMINE

CAS No: 108-91-8
EINECS: 203-629-0

Synonyms:
Cyclohexanamine; Aminocyclohexane; Hexahydroaniline; Hexahydrobenzenamine; Aminohexahydrobenzene; Cyclohexyl amine; 1-Cyclohexylamine; Aminocyclohexane; Aniline, hexahydro-; Benzenamine hexahydro-; minocylcohexane; Cyclohexylamines; cyclohexyl-amine; UNII-I6GH4W7AEG; 1-AMINO-CYCLOHEXANE; CCRIS 3645; HSDB 918; cyclohexaneamine; Cyclohexylamine.HCl; UN2357; I6GH4W7AEG; BRN 0471175; Cyclohexylamin; AI3-15323; Cyclohexylamine [UN2357] [Corrosive]; Cyclohexylamine, 99%; Cyclohexylamine [UN2357] [Corrosive]; DSSTox_CID_3996; cylohexylamine; cyclohexylarnine; cyclo-hexylamine; cyclohexane-amine; n-cyclohexylamine; cyclohexanyl amine; Hexahydro-Aniline; monocyclohexylamine; 4-Cyclohexylamine; Cyclohexylamine,(S); Hexahydro-Benzenamine; Cyclohexanamine, 9CI; CyNH2; ACMC-1BUGG; Cyclohexylamine, 99.5%; {1}-azanylcyclohexane; bmse000451; Cyclohexylamine, ReagentPlus(R), 99%; Aminocyclohexane pound>>Hexahydroaniline; Cyclohexylamine 1000 microg/mL in Methanol; Cyclohexylamine, ReagentPlus(R), >=99.9%; Aminocyclohexane, Aminohexahydrobenzene; Hexahydroaniline; Hexahydrobenzenamine; siklohegzilamin; sikloheksilamin; siklohegsilamin; siklohekzilamin; sigloheksilamin; siglohekzilamin; siglohegzilamin; sikloheksil amin, siklohekzil amin; siklohegzil amin; amino siklohegzan; aminosiklohekzan; siklohegzil-amin; siklohekzan amin; siglohegzan amin; siklohegzilamin %99; 1-amino-siklohegzan; 1-amino-sigloheksan; aminosiglohekzan  

Molecular Weight: 99.17 g/mol
Formula: C₆H₁₁NH₂
Solubility: Miscible

Physical Description
Cyclohexylamine appears as a clear colorless to yellow liquid with an odor of ammonia. Flash point 90°F. Irritates the eyes and respiratory system. Skin contact may cause burns. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.

Color/Form
Colorless or yellow liquid.
Colorless to yellow liquid with an odor of ammonia.

Odor
Strong, fishy, amine odor.

Boiling Point
274.1 °F at 760 mm Hg (EPA, 1998)

Melting Point
0.1 °F (EPA, 1998)

Flash Point
88 °F (EPA, 1998)

Solubility
Very soluble (NTP, 1992)

Density
0.8647 at 77 °F (EPA, 1998)

Vapor Density
3.42 (EPA, 1998) (Relative to Air)

Decomposition
When heated to decomposition it emits toxic fumes of NOx /nitrogen oxides/.

pH
STRONG BASE

Other Experimental Properties
On distillation with water, cyclohexylamine forms azeotropic mixt, boiling @ 96.4 °C @ 760 mm Hg; reacts with excess ammonia and zinc chloride @ 350 °C to produce alpha-picoline.

Cyclohexylamine showed dose dependent kinetics after administration of single oral doses of 35, 200, or 500 mg/kg in rats, with a reduction in plasma clearance from 37 to 24 ml/min/kg, an increase in apparent half-life from 11.8 to 12 hr, and an increased area under the testicular concentration vs time curve. Saturation of cyclohexylamine uptake by rat renal cortical slices in vitro and of renal tubular secretion in vivo occurred at concentrations and doses comparable to the oral dose studies. Cyclohexylamine clearance from a 10 mg/kg infusion was 2.58 + or - 1.13 ml/min and from a 200 mg/kg infusion, 2.49 + or - 1.65 ml/min. The cyclohexylamine to inulin clearance ratios were 2 at a dose of 10 mg/kg and 1.23 at a dose of 200 mg/kg. During chronic dietary administration the concentrations of cyclohexylamine in the plasma and testes showed a pronounced diurnal variation in rats, reaching a peak concentration at the end of the dark cycle at 6 AM (6.3 + or - 1.5 ug/ml in plasma an 45.7 + or - 3.4 ug/g in testes. The lowest concentrations of cyclohexylamine were at 9 PM (1.5 + of - 0.5 ug/ml in plasma and 10.9 + or - 3.6 ug/g in testes). The steady state plasma clearance was 33 ml/min/kg. The concentrations of cyclohexylamine in the plasma and testes of rats showed a nonlinear relationship to dietary intake. Elevated concentrations were found at intake greater than 200 mg/kg/day.

Generally, cyclohexylamine, is readily absorbed & rapidly excreted from the body. After admin to rats, cyclohexylamine appears in body tissues with the highest concn in the lungs, spleen, liver, adrenals, heart, GI tract & kidneys.

After oral admin (0.2 g/kg) to rabbits, cyclohexylamine gave rise to unchanged cyclohexylamine & N-hydroxycyclohexylamine in the urine. When C14-labeled cyclohexylamine was admin, 68% of the radioactivity was recovered in the urine after 60 hr. A small amount (0.5%) was eliminated in the breath & 45% of the admin dose was shown to be excreted in the urine as unconjugated cyclohexylamine, 0.2% as N-hydroxycyclohexylamine in conjugated form, & 2.5% as cyclohexanone oxime. The authors postulated the latter metabolite to be an artifact formed form the glucuronide of N-hydroxycyclohexylamine during the hydrolysis procedure.

The metabolites identified indicated that in rats, the metabolism of cyclohexylamine was mainly through hydroxylation of the cyclohexane ring, in man by deamination & in guinea pigs & rabbits by ring hydroxylation & deamination. The metabolites to cyclohexylamine were excreted in both free & conjugated forms.

Most of the cyclohexylamine given by gavage or intraperitoneal injection to rats and guinea pigs was excreted unchanged, and only 4-5% was metabolized within 24 hours. In rabbits, 30% was metabolized. Cyclohexylamine has been reported to be metabolized further to cyclohexanone and then to cyclohexanol in guinea pigs, rabbits and rats. A number of hydroxylated products of cyclohexylamine have been reported in these species, which were excreted in part as glucuronides.

Orally administration cyclamate appears to be readily absorbed by rabbits but less readily by guinea pigs, rats and humans. All of these species convert cyclamate to cyclohexylamine, via the action of gastrointestinal microflora on unabsorbed cyclamate. The metabolism of cyclohexylamine to other products differs somewhat in humans and other species, although most cyclohexylamine is rapidly excreted unchanged in the urine. In rats, it is metabolized mainly by hydroxylation of the cyclohexane ring; in humans, it is metabolized by deamination; and in guinea pigs and rabbits, it is metabolized by ring hydroxylation and deamination.

Mice were fed cyclohexylamine (as the hydrochloride) at a constant intake of 400 mg/kg/day for 13 weeks. Food intake and body weight gain were not affected. The metabolism of (14)C labeled cyclohexylamine administered as a single oral dose (2 uCi per mouse) was not significantly different among animals chronically fed cyclohexylamine for 0, 3, 7, or 13 weeks. The major metabolite produced was 3-aminocyclohexanol; total metabolism was less than 2%. ... Concentrations of cyclohexylamine in plasma (ug/ml) after 3 weeks feeding were 0.20; after 7 weeks 0.18; and after 13 weeks, 4.51 + or - 2.94. Concentrations of the chemical in testes (ug/g wet weight) varied from 6.81 + or - 5.21 at 3 weeks to 4.51 + or - 2.94 at 13 weeks. /Cyclohexylamine hydrochloride/

Wistar and DA rats were fed cyclohexylamine (as the hydrochloride) at constant intake of 400 mg/kg/day for 13 weeks. The metabolism of (14)C-labeled cyclohexylamine administered as a single oral dose (8 uCi per rat) was similar for both strains of rat, with no consistent effect due to age or prolonged feeding with cyclohexylamine. However, there was reduced elimination of (14)C in the treated Wistar and DA rats compared to that in the controls during the first 6 hr after dosing; the difference was statistically significant at 3 weeks in both strains and at 13 weeks in the DA strain. The major metabolites produced were 3- and 4-aminocyclohexanols; at 13 weeks the total metabolism was 17% to 18% for the Wistar rats, 4% to 6% in the DA rats. After 13 weeks, testicular atrophy was demonstrated in both strains of rat fed cyclohexylamine; DA rats appeared more sensitive to testicular toxicity than the Wistar rats. Concentrations of cyclohexylamine and its metabolites in plasma and in testicular tissue were higher in Wistar rats than in DA rats.

Cyclohexylamine can be formed to a variable extent by microbial biotransformation of cyclamate in the gastrointestinal tract of all species studied; after absorption, it is further metabolized to several compounds that are excreted in the urine.

Biological Half-Life
Cyclohexylamine showed dose dependent kinetics after administration of single oral doses of 35, 200 or 500 mg/kg in mice, with a reduction in plasma clearance from 61 to 53 ml/min/kg, an increase in apparent half-life from 1.4 to 3.5 hr, and an increased area under the testicular concentration vs time curve. During chronic dietary administration the concentrations of cyclohexylamine in the plasma and testes showed little diurna variation. The steady state plasma clearance was 65 ml/min/kg. The concentrations of cyclohexylamine in the plasma and testes of the mice showed a linear relationship to dietary intake, even at the highest intake, about 900 mg/kg/day.

Evidence for Carcinogenicity
A4: Not classifiable as a human carcinogen.

Health Effect Code(s)
HE14 - Irritation-Eyes, Nose, Throat, Skin---Marked

HE2 - Chronic (Cumulative) Toxicity---Known or Suspected animal or human carcinogen, mutagen (except Code HE1 chemicals)

HE7 - Nervous System Disturbances---Nervous system effects other than narcosis

Exposure Routes
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact.

Inhalation Symptoms
Burning sensation. Cough. Laboured breathing. Nausea. Vomiting.

Skin Symptoms
Redness. Pain. Skin burns.

Eye Symptoms
Redness. Pain. Severe deep burns.

Ingestion Symptoms
Dizziness. Abdominal cramps. Burning sensation. Vomiting. Abdominal pain. Shock or collapse. Nausea.

Advanced treatment: 
Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

Cyclohexylamines
A family of alicyclic hydrocarbons containing an amine group with the general formula R-C6H10NH2.

Cyclohexylamine    Cyclohexylamine is produced by two routes, the main one being hydrogenation of aniline using cobalt or nickel catalysts:
Cyclohexylamine    It is a useful intermediate in the production of many other organic compounds.
Cyclohexylamine    It is also prepared by alkylation of ammonia using cyclohexanol.
Cyclohexylamine    Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to sulfenamide-based reagents used as accelerators for vulcanization. It is a building block for pharmaceuticals (e.g., mucolytics, analgesics, and bronchodilators). The amine itself is an effective corrosion inhibitor. Some sweeteners are derived from this amine, notably cyclamate. The herbicide hexazinone is derived from cyclohexylamine.
Cyclohexylamine    Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a weak base, compared to strong bases such as NaOH, but it is a stronger base than its aromatic analog, aniline.
Cyclohexylamine    It is flammable, with flash point at 28.6 °C. It is toxic by both ingestion and inhalation; the inhalation itself may be fatal. It readily absorbs through skin, which it irritates. It is corrosive. Cyclohexylamine is listed as an extremely hazardous substance as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. It has been used as a flushing aid in the printing ink industry.
Cyclohexylamine    In regards to occupational exposures, the National Institute for Occupational Safety and Health has suggested workers not be exposed to a recommended exposure limit of over 10 ppm (40 mg/m) over an eight-hour workshift.
Cyclohexylamine oxidase    In enzymology, a cyclohexylamine oxidase () is an enzyme that catalyzes the chemical reaction
Cyclohexylamine oxidase    This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-NH2 group of donors with oxygen as acceptor. The systematic name of this enzyme class is cyclohexylamine:oxygen oxidoreductase (deaminating). This enzyme participates in caprolactam degradation. It employs one cofactor, FAD.
Cyclohexylamine oxidase    The 3 substrates of this enzyme are cyclohexylamine, O, and HO, whereas its 3 products are cyclohexanone, NH, and HO.