Putrescine
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Putrescine
structure -
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CAS No:
110-60-1
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Formula:
C4H12N2
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Chemical Name:
Putrescine
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Synonyms:
1,4-Butanediamine;Tetramethylenediamine;1,4-Diaminobutane;Putrescine;Putrescin;1,4-Butylenediamine;1,4-Tetramethylenediamine;1,4-Diamino-n-butane;α,ω-Butanediamine;NSC 60545;Putramine;Putrascine
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CAS No:
Description
colourless liquidChEBI: A four-carbon alkane-alpha,omega-diamine. It is obtained by the breakdown of amino acids and is responsible for the foul odour of putrefying flesh.Putrescine is a low-molecular-weight nitrogenous base with the systematic name 1,4-diaminobutane. It is an aliphatic diamine belonging to the group of biogenic amines (Bas). Two basic amino groups are present, which at the physiological pH of 7.4 carry a positive charge that makes them suitable for a wide range of functions in
Solid
Putrescine is a four-carbon alkane-alpha,omega-diamine. It is obtained by the breakdown of amino acids and is responsible for the foul odour of putrefying flesh. It has a role as a fundamental metabolite and an antioxidant. It is a conjugate base of a 1,4-butanediammonium.|Putrescine is a toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine. Putrescine is a solid. This compound belongs to the polyamines. These are compounds containing more than one amine group. Known drug targets of putrescine include putrescine-binding periplasmic protein, ornithine decarboxylase, and S-adenosylmethionine decarboxylase proenzyme.|Putrescine is a four carbon diamine produced during tissue decomposition by the decarboxylation of amino acids. Polyamines, including putrescine, may act as growth factors that promote cell division; however, putrescine is toxic at high doses.|A toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine.
Putrescine Basic Attributes
88.15
88.15
605282
203-782-3
V10TVZ52E4
60545
DTXSID4041107
C129011
Colorless oil|Colorless crystals|Leaflets
29212900
Characteristics
52
-0.70
Clear colorless to slightly yellow lyophilized powder
0.877 g/cu cm at 25 deg C
27.5 °C
158.5 °C
125 °F
n 20/D 1.457(lit.)
H2O: almost transparency;cell culture medium: 0.16 mg/mL
−20°C
436 Pa (25 °C)
Oral-Mouse LDL0: 1600 mg/kg
Open flame is flammable; high heat decomposes toxic nitrogen oxide fumes
0.7-11.2%(V)
Strong piperidine-like odor
10.8(at 20 °C)
Henry's Law constant = 3.54X10-10 atm-cu m/mol at 25 °C (est)
pKa = 10.80 (conjugate acid)
Crystals on cooling|When heated to decompoistion it emits toxic fumes of NOx.|Crystals from 85% alcohol, mp >275 °C /Putrescine hydrochloride/|Hydroxyl radical reaction rate constant = 6.62X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
II
8
UN 2928 6.1/PG 2
3
11-21/22-23-34-10
16-26-36/37/39-45
EJ6800000
F,T
Storehouse ventilated at low temperature and dry; stored separately from oxidants, acids, food and chemical additives
Stable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents. Flammable.
P210-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338-P370 + P378
H226-H302-H311-H314-H330
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. /1,4-Diaminobutane dihydrochloride 97%/
|Danger|H226 (84.18%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 199 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
PERSONAL PROTECTIVE EQUIPMENT Respiratory: Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Hand: Compatible chemical-resistant gloves. Eye: Chemical safety goggles. /1,4-Diaminobutane dihydrochloride 97%/
Water spray. Carbon dioxide, dry chemical powder, or appropriate foam. Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes. /1,4-Diaminobutane dihydrochloride 97%/
Sweep up, place in a bag and hold for waste disposal. Avoid raising dust. Ventilate area and wash spill site after material pickup is complete. /1,4-Diaminobutane dihydrochloride 97%/
Do not breathe dust. Avoid contact with eyes, skin, and clothing. Avoid prolonged or repeated exposure. /1,4-Diaminobutane dihydrochloride 97%/|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.
Irritating to eyes, respiratory system and skin. /1,4-Diaminobutane dihydrochloride 97%/
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Tetramethylenediamine is produced, as an intermediate or a final product, by process units covered under this subpart.
| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.| 0 - Materials that in themselves are normally stable, even under fire conditions.
Putrescine was tested for but not detected in gasoline nor diesel exhaust(1).
Toxicity
moderately toxic
IDENTIFICATION AND USE: Putrescine is found as colorless oil or crystals or leaflets with a strong piperidine like odor. It is very soluble in water. This chemical is used as a tool in biochemical research and as a chemical intermediate, complexing agent, catalyst in resin technology and synthesis of quaternary ammonium compounds. HUMAN EXPOSURE AND TOXICITY: Putrescine is a skin, eye and respiratory irritant. Occupational exposure to putrescine 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 putrescine by ingestion of certain meats. ANIMAL STUDIES: Putrescine caused a dose related decrease in blood pressure after intravenous administration in rats. The subacute toxicity of putrescine was examined in rats. Putrescine was administered in the diets. Adverse effects were also observed in the high dose group which included decreased body weights associated with diminished food intake was observed.
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.
LD50 Rat sc 1625 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Rat iv 760 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Mouse ip 1400 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Mouse sc 1880 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Mouse iv 510 mg/kg /1,4-Diaminobutane dihydrochloride 97%/
LD50 Rat sc 1625 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Rat iv 760 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Mouse ip 1400 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Mouse sc 1880 mg/kg /1,4-Diaminobutane dihydrochloride 97%/|LD50 Mouse iv 510 mg/kg /1,4-Diaminobutane dihydrochloride 97%/
Putrescine is a biogenic polyamine and precursor of permidine. It was initially detected in decaying animal tissues, but now known to be present in all cells and certain bacterial cultures and is essential for both normal and neoplastic tissue growth(1).
Putrescine's production and use in biochemical research(1) and as a chemical intermediate(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a log Kow of -3.42(2) and a regression-derived equation(3), indicates that putrescine is expected to have very high mobility in soil(SRC). However, the pKa of putrescine is 10.80(4), indicating that this compound will almost entirely exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Putrescine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3 mm Hg at 25 °C(SRC), determined from a fragment constant method(6). Biodegradation data in soil were not available(SRC, 2010).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a log Kow of -3.42(2) and a regression-derived equation(3), indicates that putrescine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 10.80(4) indicates putrescine 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(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), 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), putrescine, which has an estimated vapor pressure of 2.33 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 putrescine 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 hrs(SRC), calculated from its rate constant of 6.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Putrescine 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).
The rate constant for the vapor-phase reaction of putrescine with photochemically-produced hydroxyl radicals has been estimated as 6.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Putrescine is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(2). Putrescine does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for putrescine(SRC), using a log Kow of -3.42(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc of putrescine is estimated as 49(SRC), using a log Kow of -3.42(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that putrescine is expected to have very high mobility in soil. However, the pKa of putrescine is 10.80, indicating that this compound will almost entirely exist 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).
A pKa of 10.80(1) indicates putrescine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water and moist soil surfaces is not expected to be an important fate process. Putrescine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3 mm Hg(SRC), determined from a fragment constant method(2).
Putrescine levels in fresh pork and beef meat were not detected to 0.6 mg/kg and not detected to 1.75 mg/kg, respectively. Levels in cooked ham and mortadella were not detected to 3.9 mg/kg and not detected to 3.9 mg/kg, respectively. The putrescine content in ripened meat products ranged from 31.6 to 361.9 mg/kg chorizo and 85.9 to 184.5 mg/kg in salchichon(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that three workers (three of these were female) were potentially exposed to putrescine in the US(1). Occupational exposure to putrescine may occur through inhalation and dermal contact with this compound at workplaces where putrescine is produced or used. Monitoring data indicate that the general population may be exposed to putrescine via ingestion of certain meats(SRC).
Drug Information
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.
Putrescine is synthesized biologically via two different pathways, both starting from arginine. In one pathway, arginine is converted into agmatine, with a reaction catalyzed by the enzyme arginine decarboxylase (ADC); then agmatine is transformed into carbamilputrescine by agmatine imino hydroxylase (AIH). Finally, carbamilputrescine is converted into putrescine. In the second pathway, arginine is converted into ornithine and then ornithine is converted into putrescine by ornithine decarboxylase (ODC).|Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn ... /reacts with/ attacks another s-adenosyl methionine and converts it to spermine.|Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.|A novel bacterial putrescine utilization pathway was discovered. Seven genes, the functions of whose products were not known, are involved in this novel pathway. Five of them encode enzymes that catabolize putrescine; one encodes a putrescine importer, and the other encodes a transcriptional regulator. This novel pathway involves six sequential steps as follows: 1) import of putrescine; 2) ATP-dependent gamma-glutamylation of putrescine; 3) oxidization of gamma-glutamylputrescine; 4) dehydrogenation of gamma-glutamyl-gamma-aminobutyraldehyde; 5) hydrolysis of the gamma-glutamyl linkage of gamma-glutamyl-gamma-aminobutyrate; and 6) transamination of gamma-aminobutyrate to form the final product of this pathway, succinate semialdehyde, which is the precursor of succinate.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/SIGNS AND SYMPTOMS/ Skin, eye and respiratory irritant. /Putresine dihydrochloride/
1,4 Butanediamine
Putrescine Use and Manufacturing
The reaction of pyrrole with hydroxylamine hydrochloride produces succinimide, which is then reduced to obtain succinimide.
A GABA precursor in many biological systems.
Drumming
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7614]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,4-Butanediamine. Aggregated National Production Volume: <500,000 pounds.
All other basic organic chemical manufacturing|1,4-Butanediamine: ACTIVE|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 ...|Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound NH2(CH2)4NH2 (1,4-diaminobutane or butanediamine). It is related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms. The two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semen and some microalgae, together with related molecules like spermine and spermidine.
Agrochemicals -> Attractants
Computed Properties
Molecular Weight:88.15
XLogP3:-0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:88.100048391
Monoisotopic Mass:88.100048391
Topological Polar Surface Area:52
Heavy Atom Count:6
Complexity:17.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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