Basic information
- Standard SMILES
NCCCCCN- InChIKey
VHRGRCVQAFMJIZ-UHFFFAOYSA-N- Molecular formula
- C5H14N2
- Average molar mass
- 102.18 g/mol
- Monoisotopic mass
- 102.11569846
Names & identifiers
- Preferred name
- Cadaverine
- IUPAC
- pentane-1,5-diamine
- English name
- 1,5-Diaminopentane
- Molecular formula
- C5H14N2
- Molecular weight
- 102.18
Names & synonyms
Show more names
Database identifiers
- CAS
462-94-2- PubChem CID
- 273
- DTXSID
DTXSID5075448- ChEMBL
CHEMBL119296- ChEBI
CHEBI:18127- UNII
- L90BEN6OLL
- EC Number
- 207-329-0
- Nikkaji
- J5.771A
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 52 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 25
Experimental & physicochemical properties
Odor
Characeteristic odor
... partially responsible for the distinctive smell of urine and semen
Color/Form
Syrupy, colorless liquid
Thick fuming liquid
Melting Point
11.83 °C
9 °C
Physical Description
CBI
Colorless syrupy liquid that fumes in air; mp = 9 deg C; [Merck Index] Colorless hygroscopic liquid with an amine-like odor; [Alfa Aesar MSDS]
Liquid
Physicochemical properties
- Melting point
- 9 °C · 9 °C
- Boiling point
- 178 · 178-180 °C(lit.)
- Density
- 0.873 g/mL · 0.873 g/mL at 25 °C(lit.)
- vapor pressure
- 1.29 · 1.29-17hPa at 20-25℃
- refractive index
- 20 · n20/D 1.458(lit.)
- Flash point
- 145 °F · 145 °F
- solubility
- 1 M · 1 M HCl: soluble0.5g/10 mL, clear, colorless
- form
- Liquid
- pka
- 10.05 · 10.05(at 25℃)
- color
- Clear colorless to yellow
- Odor
- characteristic odor
- Viscosity
- 3.029 mm2/s · 3.029mm2/s
- Water Solubility
- soluble
- Sensitive
- Air Sensitive & Hygroscopic
- Merck
- 14 · 14,1609
- BRN
- 1697256 · 1697256
- Stability
- Stable. Incompatible with acid chlorides, acids, acid anhydrides, strong oxidizing agents, carbon dioxide.
- InChI
- 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
- InChIKey
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N
- SMILES
- NCCCCCN
- LogP
- -0.3 · -0.3--0.15 at 21℃
- CAS DataBase Reference
- 462 · 462-94-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 90 BEN6OLL · L90BEN6OLL
- NIST Chemistry Reference
- 1 · 1,5-Diaminopentane(462-94-2)
- EPA Substance Registry System
- Cadaverine (462-94-2)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H314-H227
- Precautionary statements
- 501 · P501-P270-P210-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 34 · 34-36/37
- Safety Statements
- 26 · 26-36/37/39-45-25-27
- RIDADR
- 2735 · UN 2735 8/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 200000 · SA0200000
- F
- 10 · 10
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29212900 · 29212900
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Corr. 1B
- Hazardous Substances Data
- 462 · 462-94-2(Hazardous Substances Data)
- Toxicity
- 10 mmol/L · dni-mus:ast 10 mmol/L AMOKAG 33,149,79
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H302+H312 (64.2%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal];H302 (68.5%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (71%): Harmful in contact with skin [Warning Acute toxicity, dermal];H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H318 (70.4%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 162 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: 1,5-Pentanediamine
1,5-Pentanediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,5-Pentanediamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Status: Active Update: 02-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/16098;Status: Active Update: 18-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27754
1,5-Pentanediamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards Summary
A strong base that attracts carbon dioxide; A skin irritant and possible sensitizer; [Merck Index] Causes burns; [HSDB] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] Search for (462-94-2[EC/RN Number]) AND (sensitizer OR sensitization OR allergic OR dermatitis): no papers confirming skin sensitization; [PubMed] See 1,6-Diaminohexane.
NFPA Hazard Classification
3 - Materials that, under emergency conditions, can cause serious or permanent injury.
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
0 - Materials that in themselves are normally stable, even under fire conditions.
Safety & protection
Disposal Methods
This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: dispose of as unused product.
Preventive Measures
Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Personal Protective Equipment (PPE)
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Hand protection: Handle with gloves. Eye protection: Safety glasses Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.
Safety glasses, good ventilation, gloves
Toxicology
Interactions
Histamine poisoning can result from the ingestion of food containing unusually high levels of histamine. ... Histamine poisoning is characterized by a short incubation period, a short duration, and symptoms resembling those associated with allergic reactions. The evidence supporting the role of histamine as the causative agent is compelling. ... Histamine ingested with spoiled fish appears to be much more toxic than histamine ingested in an aqueous solution. The presence of potentiators of histamine toxicity in the spoiled fish may account for this difference in toxicity. Several potentiators including other putrefactive amines such as putrescine and cadaverine have been identified. Pharmacologic potentiators may also exist; aminoguanidine and isoniazid are examples. The mechanism of action of these potentiators appears to be the inhibition of intestinal histamine-metabolizing enzymes. This enzyme inhibition causes a decrease in histamine detoxification in the intestinal mucosa and results in increased intestinal uptake and urinary excretion of unmetabolized histamine.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is expected to have high mobility in soil(SRC). However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Cadaverine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2010).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is not expected to adsorb to suspended solids and sediment(SRC). The pKa values of 9.13 and 10.25(3) indicate cadaverine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -0.15(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2010).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cadaverine, which has a /an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cadaverine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its rate constant of 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Cadaverine does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
Cadaverine levels in fresh pork and beef meat were not detected to 0.7 mg/kg and not detected, respectively. Levels in cooked ham and mortadella were not detected to 0.9 mg/kg and not detected to 7.9 mg/kg, respectively. The cadaverine content in ripened meat products ranged from 3.9 to 34.9 mg/kg chorizo and 2.1 to 68.5 mg/kg in salchichon(1).
Toxicity Summary
IDENTIFICATION AND USE: Cadaverine is a syrupy, colorless liquid with a distinctive odor of urine and semen. It is soluble in water, ethanol; slightly soluble in ethyl ether, and miscible in water. It is used in the production of high polymers, as a chemical intermediate, and in biological research. HUMAN EXPOSURE AND TOXICITY: It is a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin. Harmful if ingested, inhaled, or absorbed through the skin. It can cause burns and is very destructive of mucous membranes. Occupational exposure to cadaverine may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. Monitoring data indicate that the general population may be exposed to cadaverine by ingestion of certain meats. ANIMAL STUDIES: In In rats, cadaverine had a low oral toxicity. Cadaverine caused a dose-related decrease in blood pressure after intravenous administration in rats. The subacute toxicity of this chemical was examined in rats. Cadaverine was administered in the diet to groups of 10 male and 10 female rats. Adverse effects were observed in the high dose group and decreased body weights associated with diminished food intake were observed. Slight increases in packed cell volume, hemoglobin concentration, and thrombocytes occurred with chemical exposure.
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of cadaverine can be estimated to be 90(SRC). According to a classification scheme(2), this estimated Koc value suggests that cadaverine is expected to have high mobility in soil. However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
Natural Pollution Sources
Cadaverine is a ptomaine formed in the decay of animal proteins after death(1). It is also produced in small quantities by living beings and is partially responsible for the distinctive smell of urine and semen(2). It is related to putrescine. Both are produced by the breakdown of amino acids in living and dead organisms(3).
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Cadaverine ... a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin.
/SIGNS AND SYMPTOMS/ Stench! Harmful if ingested, inhaled, or absorbed through the skin. Corrosive - causes burns. Very destructive of mucous membranes.
Regulatory information
Regulatory Information
Chemical: 1,5-Pentanediamine
1,5-Pentanediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,5-Pentanediamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Status: Active Update: 02-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/16098;Status: Active Update: 18-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27754
1,5-Pentanediamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Safety data
- F
- 10
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SA0200000
- ridadr
- UN 2735 8/PG 3
- hs_code
- 29212900
- Toxicity
- dni-mus:ast 10 mmol/L AMOKAG 33,149,79
- risk_code
- 34-36/37
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- C
- safety_code
- 26-36/37/39-45-25-27
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H301-H314-H227
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- Precautionary statements
- P501-P270-P210-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
- Hazardous Substances Data
- 462-94-2(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
It is a precursor of piperidine, which has been linked with some functional stages of the CNS. Cadaverine is the source of much of the piperidine excreted in the urine.
Cadaverine ... a relatively nontoxic ptomaine, C5H14N2, formed by decarboxylation of lysine; it is sometimes one of the products of Vibrio proteus and of V. cholerae, and occasionally found in the urine in cystinuria, where it causes an unpleasant odor.
Cadaverine is synthesized from lysine in a one-step reaction with lysine decarboxylase (LDC).
Absorption, Distribution and Excretion
The urinary excretion of histamine, methylhistamine, putrescine, cadaverine, spermidine and spermine was examined before, during and after pregnancy in rats. During the last third of undisturbed pregnancy a distinct and steep rise occurred in the excretion of all amines studied except spermine. The peak values were found a few days before the birth of the young. In spermidine excretion a second peak was observed one or two days after delivery. Before and during the first 2 weeks of gestation on a molar basis putrescine excretion was the greatest one. During the last trimester histamine was excreted in the largest amount. Under the influence of the diamine oxidase inhibitor aminoguanidine the general pattern of excretion of diamines and polyamines in pregnant rats remained essentially unchanged but the total amount excreted increased. Most conspicuous was the great elevation of urinary contents of putrescine and cadaverine.
Cadaverine has been shown to be present in the central nervous system (CNS) ... Its concentration in the whole brain varies during behavioral sleep in mammals and during hibernation in molluscs. ... Cadaverine has been considered a non-metabolite of the brain, and its presence in the body was believed to be due almost entirely to bacterial decarboxylation of lysine in the intestine. In slices of mouse brain, exogenous cadaverine accumulates against a concentration gradient and can reach a concentration ten times greater in the tissue than in the surrounding medium. The question has been therefore: does the cadaverine in the brain originate from an exogenous source; is it formed and resorbed in the intestine? Assaying cadaverine in axenic mice, /it has been/ found that this is not the case, and that there is an endogenous source of cadaverine in the mouse.
Uses & manufacturing
Uses
A foul-smelling diamine formed by bacterial decarboxylation of lysine. [ChemIDplus] Biogenic polyamine present in cholera discharge; [Merck Index] Formed from decay of animal proteins; Used to make high polymers, as an intermediate, and in biological research; [HSDB]
Preparation of high polymers, intermediate, biological research.
General Manufacturing Information
Asphalt Paving, Roofing, and Coating Materials Manufacturing;All Other Basic Organic Chemical Manufacturing;Oil and Gas Drilling, Extraction, and Support activities
1,5-Pentanediamine: ACTIVE
A ptomaine formed in the decay of animal proteins after death
... also made synthetically
Biogenic amines are non-volatile amines formed by decarboxylation of amino acids. Although many biogenic amines have been found in fish, only histamine, cadaverine, and putrescine have been found to be significant in fish safety and quality determination. Despite a widely reported association between histamine and scombroid food poisoning, histamine alone appears to be insufficient to cause food toxicity. Putrescine and cadaverine have been suggested to potentiate histamine toxicity. With respect to spoilage on the other hand, only cadaverine has been found to be a useful index of the initial stage of fish decomposition ...
Cadaverine - A syrupy, colorless, fuming ptomaine formed by the carboxylation of lysine by bacteria in decaying animal flesh.
Applications
Uses1,5-Diaminopentane is mainly used in organic synthesis.
UsesCadaverine is a diamine that can be used in hetarylation with halopyridines (2-bromo, 2-iodo, and 3-iodo-pyridines) to synthesize N,N′-dipyridinyl diamine derivatives in the presence of CuI-2-isobutyrylcyclohexanone as a catalyst. It can also be used to synthesize a poly-imidazolium polymer with high thermal stability by reacting with acetic acid, pyruvaldehyde and formaldehyde by modified Debus-Radziszewski reaction.
General DescriptionCadaverine, a biogenic amine, belongs to the class of aliphatic diamines and is commonly found in food products including cheese, fish products, fermented sausages, fish sauces, etc. It can be used as a freshness marker and as an indicator of microbial spoilage since it is most commonly identified in food products as a result of inappropriate storage conditions and microbial contamination.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: An alkane-alpha,omega-diamine comprising a straight-chain pentane core with amino substitutents at positions 1 and 5. A colourless syrupy liquid diamine with a distinctive unpleasant odour, it is a homologue of putresceine and is formed by the bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. It is also found in plants such as soyabean.
Related reactions
Linked notes
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