基本情報
- 標準SMILES
CC1OC(C)OC(C)O1- InChIKey
SQYNKIJPMDEDEG-UHFFFAOYSA-N- 分子式
- C6H12O3
- 平均分子量
- 132.16 g/mol
- 単同位体質量
- 132.07864424
名称と識別子
- 優先名称
- Paraldehyde
- IUPAC
- 2,4,6-trimethyl-1,3,5-trioxane
- 現地名
- パラアルデヒド
- 英語名
- Paraldehyde
- 分子式
- C6H12O3
- 分子量
- 132.16
名称と別名
名称をさらに表示
データベース識別子
- CAS
123-63-7、1499-02-1- PubChem CID
- 31264
- DTXSID
DTXSID9023419- ChEMBL
CHEMBL1410743- ChEBI
CHEBI:27909- UNII
- S6M3YBG8QA
- EC Number
- 204-639-8
- Nikkaji
- J5.543C
物性
構造計算による物性
- XLogP
- 0.7
- 極性表面積
- 27.7 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 0
- 重原子数
- 9
- 形式電荷
- 0
- 複雑度
- 63
実験および物理化学的性質
LogP
0.73
Log Kow = 0.67
0.67
0.67
Odor
CHARACTERISTIC AROMATIC ODOR
Agreeable odor
Taste
DISAGREEABLE TASTE
Burning taste
Density
0.9943 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9923 @ 20 °C/4 °C
SPECIFIC HEAT 0.434; BULK DENSITY 8.27 LB/GAL (20 °C)
0.99 g/cm³
0.9943 @ 20°C
Solubility
Sparingly soluble (NTP, 1992)
125g/L
SOL IN 8 PARTS WATER AT 25 °C; 17 PARTS BOILING WATER
Sol in water: 1 in 9 parts at 20 °C, 1 in 10 parts at 30 °C, & 1 in 11.5 parts at 37 °C
Sol in sodium chloride solution: 1 in 9.5 parts at 20 °C, 1 in 11 parts at 30 °C, & 1 in 12.5 parts at 37 °C
MISCIBLE WITH ALC, CHLOROFORM, ETHER, OILS
Flash Point
96 °F (NTP, 1992)
96 °F (OPEN CUP)
24 °C c.c.
Boiling Point
262 °F at 760 mmHg (NTP, 1992)
124
124.5 °C
123.00 to 124.00 °C. @ 760.00 mm Hg
124.5 °C
124.3 °C @760 [mm Hg]
Melting Point
54.7 °F (NTP, 1992)
12
12.6 °C
12.6 °C
12.6 °C
12.6 °C
Vapor Density
4.5
Relative vapor density (air = 1): 4.5
物理化学的性質
- 融点
- 12 °C · 12 °C
- 沸点
- 65 · 65-82 °C
- 比重(密度)
- 0.994 g/mL · 0.994 g/mL at 20 °C (lit.)
- 蒸気密度
- 1.52 · 1.52 (vs air)
- 蒸気圧
- 25.89 psi · 25.89 psi ( 55 °C)
- 屈折率
- 20 · n20/D 1.39
- FEMA
- 4010 · 4010 | PARALDEHYDE
- 闪点
- 30 °F · 30 °F
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 120 g/リットル · 120g/リットル
- 酸解離定数(Pka)
- 16 · 16(at 25℃)
- 外見
- 解決
- 色
- 無色の液体
- 比重
- 0.994 · 0.994
- 臭い (Odor)
- 不快な味、芳香臭
- 爆発限界(explosive limit)
- 1.3 · 1.3-17.0%(V)
- 水溶解度
- 125 g/L · 125g/L(25℃)
- JECFA Number
- 2299 · 2299
- Merck
- 13 · 13,7098
- BRN
- 80142 · 80142
- Henry's Law Constant
- 5.8 · 5.8×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 14.5 · 14.5(20℃)
- 安定性
- 安定。可燃性。強力な酸化剤、鉱酸とは相容れない。
- InChI
- 1S/C6H12O3/c1-4-7-5(2)9-6(3)8-4/h4-6H,1-3H3
- InChIKey
- SQYNKIJPMDEDEG-UHFFFAOYSA-N
- SMILES
- CC1OC(C)OC(C)O1
- LogP
- 0.67 · 0.670
- CAS データベース
- 123 · 123-63-7(CAS DataBase Reference)
- NISTの化学物質情報
- Paraldehyde(123-63-7)
- EPAの化学物質情報
- Paraldehyde (123-63-7)
化学的性質
化学的特性Paraldehyde is a colourless to yellowish clear liquid. Pleasant, sweet odor. Less dense than water. Vapors are heavier than air.
安全と法規制
GHS分類
GHS Classification
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1566) of reports.
危険有害性情報
Regulatory Information
Chemical: 1,3,5-Trioxane, 2,4,6-trimethyl-
DEA schedule IV controlled substance
SP - indicates a substance that is identified in a proposed Significant New Use Rule.
Status: Active Update: 21-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11337
1,3,5-Trioxane, 2,4,6-trimethyl-: HSNO Approval: HSR001209 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: Emits toxic fumes on heating.;Behavior in Fire: Can react vigorously when exposed to heat or flame. Vapor is heavier than air and may travel a considerable distance to source of ignition and flash back. (USCG, 1999)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;· Vapors may form explosive mixtures with air.;· Vapors may travel to source of ignition and flash back.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion hazard indoors, outdoors or in sewers.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Runoff to sewer may create fire or explosion hazard.;· Containers may explode when heated.;· Many liquids will float on water.
Highly flammable. Above 24 °C explosive vapour/air mixtures may be formed.
Fire Potential
DANGEROUS, WHEN EXPOSED TO HEAT, FLAME OR OXIDIZERS.
FLAMMABLE LIQUID.
Health Hazards
INHALATION AND INGESTION: Irritation, headache, bronchitis, pulmonary edema. Irritating to digestive tract. Hypnotic and analgesic properties. Incoordination and drowsiness, followed by sleep. Larger doses-coma-weak pulse and shallow respiration, cyanosis-death from respiratory paralysis. EYES: irritation-can cause serious injury. SKIN: Dermatitis (skin inflammation). (USCG, 1999)
· May cause toxic effects if inhaled or absorbed through skin.;· Inhalation or contact with material may irritate or burn skin and eyes.;· Fire will produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.
FDA Requirements
Paraldehyde is subject to control under the Federal Control Substance Act of 1970 as a schedule IV (C-IV) drug.
Paraldehyde is an indirect food additive for use as a component of adhesives.
Derivatives designated as a habit forming drug.
Special Reports
USEPA/ECAO; Health and Environmental Effects Profile for Paraldehyde (1989) EPA/600/X-86/169. /This document contains/ both published literature and information obtained from Agency program office files were evaluated as they pertained to potential human health, aquatic life,and environmental effects of hazardous waste constituents. Existing data are insufficient to determine a reference dose or a carcinogenic potency factor for paraldehyde.
... Paraldehyde, diazepam, secobarbital and valproic acid are used when rapid effect for termination of prolonged or serial seizures is desired.[Graves NM, Kriel RL; Pediatr Neurol 3 (6): 321-6 (1987)]
安全と保護具
Fire Fighting
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.;SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842).;LARGE FIRE: Water spray, fog or alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)
Use water spray, alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch or walk through spilled material.;· Stop leak if you can do it without risk.;· Prevent entry into waterways, sewers, basements or confined areas.;· A vapor-suppressing foam may be used to reduce vapors.;· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.;· Use clean, non-sparking tools to collect absorbed material.;Large Spill;· Dike far ahead of liquid spill for later disposal.;· Water spray may reduce vapor, but may not prevent ignition in closed spaces.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.
Fire Fighting Procedures
Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Water may be ineffective. Use water spray to keep fire exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.
If material is on fire or involved in a fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.
Storage Conditions
PARALDEHYDE SHOULD BE STORED IN WELL-FILLED, TIGHT, LIGHT-RESISTANT GLASS CONTAINERS WITH A CAPACITY OF NO MORE THAN 30 ML, AT A TEMP NOT EXCEEDING 25 °C.
Store in a cool, dry, well ventilated location. Separate from alkalies, acids, iodides, oxidizing material, rubber, and plastic. Inside storage should be in a standard flammable liquids storage warehouse, room, or cabinet.
IT IS BEST STORED IN 2- OR 5-ML AMPULES, WHICH CAN BE OPENED FRESHLY & UNUSED CONTENTS DISCARDED.
Nonfire Spill Response
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.;LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024)
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.
Spillage Disposal
Remove all ignition sources. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable non-plastic containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
毒性情報
Interactions
Animal studies indicate that disulfiram slows the metabolism of paraldehyde by way of inhibition of acetaldehyde dehydrogenase resulting in an increase in blood concn of paraldehyde & acetaldehyde. Until this potential interaction is investigated in humans, paraldehyde & disulfiram should be admin together with caution.
INTERACTIONS BETWEEN PARALDEHYDE & ETHYL ALCOHOL ARE NOT WELL UNDERSTOOD ... DOSES OF 1-2 OZ IN ALCOHOLICS SOMETIMES KILL WITHIN 0.5-4 HR. IN ANIMALS ETHANOL & PARALDEHYDE ARE SYNERGISTIC BUT LESS THAN ADDITIVE IN TERMS OF LETHALITY; UNDER SOME DOSAGE SCHEDULES, HOWEVER, EXPTL DATA SUGGEST THAT THESE DRUGS ARE ANTAGONISTIC.
ADDITIVE CNS DEPRESSION MAY OCCUR WHEN PARALDEHYDE IS ADMIN CONCOMITANTLY WITH OTHER CNS DEPRESSANTS SUCH AS BARBITURATES OR ALCOHOL. SOME FATALITIES HAVE BEEN ASSOCIATED WITH CONCOMITANT USE OF ALCOHOL & PARALDEHYDE.
The increased acetate levels which may follow paraldehyde administration reportedly may increase the danger of sulfonamide crystalluria.
For more Interactions (Complete) data for PARALDEHYDE (7 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: If released to soil, paraldehyde may volatilize rapidly from soil surfaces or it may leach into deeper soil. Potential degradation products include acetaldehyde and acetic acid. (SRC)
AQUATIC FATE: If released to water, volatilization is expected to be an important, if not the dominant, fate process (half-life in a model river: 31 hr). Paraldehyde is not expected to bioaccumulate in aquatic organisms, or adsorb to suspended solids and sediments in water. (SRC)
ATMOSPHERIC FATE: Based on a vapor pressure of 25.5 mm Hg at 20 °C(1), paraldehyde is expected to exist almost entirely in the vapor phase in the atmosphere(2,SRC). Reaction with photochemically generated hydroxyl radicals is expected to be the dominant removal mechanism (half-life 45 hours). The relatively high water solubility of paraldehyde (125,000 mg/l at 25 °C(3)) suggests that this compound may also be removed from the atmosphere in precipitation(SRC).
Signs and Symptoms
Burning sensation. Cough. Shortness of breath. Further see Ingestion.
Redness. Pain.
Redness. Pain.
Burning sensation in the throat and chest. Nausea. Vomiting. Diarrhoea. Drowsiness. Unconsciousness.
Soil Adsorption/Mobility
Soil adsorption coefficients (Koc) of 7-55 were estimated for paraldehyde using linear regression equations based on a water solubility of 125,000 mg/l at 25 °C and a log Kow of 0.67(1,2,3,SRC). These Koc values suggest that paraldehyde would be very highly mobile in soil and that adsorption to suspended solids and sediments in water would be insignificant(4,SRC).
Human Toxicity Excerpts
... IT MAY PRODUCE EXCITEMENT OR DELIRIUM IN PRESENCE OF PAIN. ... IN LARGE DOSES, IT PRODUCES RESPIRATORY DEPRESSION & HYPOTENSION.
SOME DELAY IN ONSET OF RESP MOVEMENTS HAS BEEN OBSERVED IN NEONATES FOLLOWING ITS ADMIN TO MOTHER DURING LABOR.
Patients poisoned by paraldehyde commonly exhibit very rapid, labored respiratory movements. Acidosis, bleeding gastritis, muscular irritability, azotemia, oliguria, albuminuria, leukocytosis, fatty changes in the liver and kidney with toxic hepatitis and nephrosis, pulmonary hemorrhages and edema, and dilatation of the right ventricle have all been observed in cases of severe acute or chronic paraldehyde poisoning.
Chronic paraldehyde intoxication results in tolerance and dependence. The paraldehyde addict may become acquainted with the drug when it is used in the treatment of alcoholism and then, surprisingly in view of its disagreeable taste and odor, prefer it to alcohol. Paraldehyde addiction resembles alcoholism, and sudden withdrawal may result in delirium tremens and vivid hallucinations.
For more Human Toxicity Excerpts (Complete) data for PARALDEHYDE (18 total), please visit the HSDB record page.
Artificial Pollution Sources
Paraldehyde may be released to the environment in emissions or effluents from sites of its manufacture or industrial use (paraldehyde is used as a drug, chemical intermediate, dyestuff intermediate, and solvent(1)) and from disposal of wastes containing this compound (ie hospital wastes)(2,3,SRC).
Environmental Bioconcentration
Based on a water solubility of 125,000 mg/l at 25 °C and a log Kow of 0.67, bioconcentration factors (BCF) of 0.8-2 were estimated for paraldehyde(1,2,3,SRC). These BCF values suggest that paraldehyde would not bioaccumulate significantly in aquatic organisms(SRC).
法規制情報
Regulatory Information
Chemical: 1,3,5-Trioxane, 2,4,6-trimethyl-
DEA schedule IV controlled substance
SP - indicates a substance that is identified in a proposed Significant New Use Rule.
Status: Active Update: 21-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11337
1,3,5-Trioxane, 2,4,6-trimethyl-: HSNO Approval: HSR001209 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
FDA Requirements
Paraldehyde is subject to control under the Federal Control Substance Act of 1970 as a schedule IV (C-IV) drug.
Paraldehyde is an indirect food additive for use as a component of adhesives.
Derivatives designated as a habit forming drug.
RCRA Requirements
U182; As stipulated in 40 CFR 261.33, when paraldehyde, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). These standards implement Section 111 of the Clean Air Act and are based on the Administrator's determination that emissions from the SOCMI cause, or contribute significantly to, air pollution which may reasonably be anticipated to endanger public health or welfare. 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. Paraldehyde is produced, as an intermediate or final product, by process units covered under this subpart. These standards of performance become effective upon promulgation but apply to affected facilities for which construction or modification commenced after January 5, 1981.
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- YK0525000
- ridadr
- UN 1264
- 毒性
- LD50 orally in rats: 1.65 g/kg (Figot)
- PRTR法
- 1-12
- hs_code
- 29125000
- risk_code
- 11-R11-10
- 化審法
- (2)-483
- 安衛法
- 57,57-2
- 消防法
- 危-4-2-III
- hazard_code
- F
- safety_code
- 9-16-29-33-S9-S33-S29-S16
- hazard_class
- 3
- packing_group
- III
- 自然発火温度
- 235 °C
- Hazard Classifications
- Flam. Liq. 3
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 123-63-7(Hazardous Substances Data)
化学と産業
薬理情報
ATC Code
N - Nervous system;N05 - Psycholeptics;N05C - Hypnotics and sedatives;N05CC - Aldehydes and derivatives;N05CC05 - Paraldehyde
QN - Nervous system;QN05 - Psycholeptics;QN05C - Hypnotics and sedatives;QN05CC - Aldehydes and derivatives;QN05CC05 - Paraldehyde
Mechanism of Action
Paraldehyde is believed to reduce the release of acetylcholine in response to neuronal depolarization. The exact mechanism of this effect is unknown.
BELIEVED TO DEPRESS MANY LEVELS OF CNS INCLUDING ASCENDING RETICULAR ACTIVATING SYSTEM TO CAUSE IMBALANCE BETWEEN INHIBITORY & FACILITATORY MECHANISMS.
Biological Half-Life
The mean half life is 7.5 hours in a range if 3.5-9.5 hours.
The biological half-life of paraldehyde /in humans/ has been reported to be 3.5 to 9.5 hours with an average of about 7.5 hours.
Metabolism/Metabolites
Paraldehyde is believed to undergo depolymerization to acetaldehyde followed by oxidation by aldehyde dehydrogenase. It is thought to ultimately be metabolized to carbon dioxide and water.
It is believed that paraldehyde is depolymerized to acetaldehyde in the liver & then oxidized by aldehyde dehydrogenase to acetic acid, which is ultimately metabolized to carbon dioxide & water.
MeSH Pharmacological Classification
Drugs used to prevent SEIZURES or reduce their severity.
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Absorption, Distribution and Excretion
93% of orally administered paraldehyde is absorbed from the gastrointestinal tract.
70-80% is metabolized to carbon dioxide and subsequently exhaled. 11-28% is exhaled as the parent compound. 0.1-2.5% is excreted in the urine as the parent compound.
Paraldehyde is rapidly absorbed from ... IM injection sites. Maximum serum concn, which may range from 34 to 150 ug/ml, are reached within 20-60 minutes following oral admin of 10 ml ... or IM admin of 0.25 ml/kg. ... Although tissue distribution ... has not been extensively studied, it is known that the concn ... in CSF is about 25 to 30% lower than that in the blood. Maximum paraldehyde concn are reached in the CSF 30-60 minutes after oral or IM admin ...
Oral paraldehyde is rapidly absorbed and widely distributed; the drug readily crosses the placental barrier. With hypnotic doses, 70 to 80% is metabolized in the liver, most of the remainder is exhaled, and a small amount is excreted in urine.
... PARALDEHYDE EQUILIBRATES RAPIDLY BETWEEN MATERNAL & FETAL BLOODS.
FETAL/MATERNAL CONCN RATIO IS 0.94. /FROM TABLE/
用途と製造
Uses
Used as a substitute for acetaldehyde, an intermediate for dyes and other organic compounds, a solvent (fats, oils, waxes, gums, and resins), a rubber accelerator, and a medication (anticonvulsant and sedative); [HSDB] No longer prescribed as a medication; Was used as a motor fuel from 1939-1945; [Ullmann]
SUBSTITUTE FOR ACETALDEHYDE; MFR DYESTUFF INTERMEDIATES; SOLVENT FOR FATS, OILS, WAXES, GUMS, RESINS; LEATHER, MIXTURES FOR CELLULOSE DERIVATIVES
MFR ORGANIC COMPOUNDS
INDUSTRIALLY IT HAS BEEN USED AS SOLVENT & ALSO AS RUBBER ACTIVATOR & ANTIOXIDANT
Used in chemical synthesis as a source of acetaldehyde whereby resin formation and other secondary reactions are largely eliminated. ... for instance, ... production of pyridines and chlorination of chloral.
MEDICATION
Methods of Manufacturing
PREPD BY POLYMERIZATION OF ACETALDEHYDE CATALYZED BY HCL & H2SO4 AT MEDIUM TO HIGH TEMP. CATALYZED BY MIXTURE OF H2SO4 & H3PO4.
BY TREATING ACETALDEHYDE WITH SMALL QUANTITIES OF SULFUR DIOXIDE, HYDROCHLORIC ACID, CARBONYL CHLORIDE, OR ZINC CHLORIDE; ALMOST COMPLETE CONVERSION OCCURS, & BY FREEZING LIQ & THEN DISTILLING CRYSTALLIZED MATERIAL, IF NECESSARY, PURE PARALDEHYDE IS PRODUCED.
Formulations/Preparations
Grade: Technical, USP.
Paraldehyde: Oral & Rectal (liquid) Paral (C-IV) from Forest.
Paraldehyde: Parenteral (Sterile) Paraldehyde injection (C-IV) from CMC.
The British Pharmacopeia specifies that it contains a suitable amount of an antioxidant; the USA Pharmacopeia permits a suitable stabilizer.
For more Formulations/Preparations (Complete) data for PARALDEHYDE (8 total), please visit the HSDB record page.
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Environmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information
1,3,5-Trioxane, 2,4,6-trimethyl-: ACTIVE
/Paraldehyde is/ a cyclic polymer (trimer) of acetaldehyde.
応用分野
解説アセトアルデヒドCH3CHOの6員環状の三量体。パラアセトアルデヒドともよばれる。アセトアルデヒドを濃硫酸、塩酸などとともに加熱すると生成する(図)。三量体を生成する反応は可逆反応であるので、酸の作用によりアセトアルデヒドが再生される。特有のにおいをもつ無色の液体で、水にかなり溶け、エタノール(エチルアルコール)、エーテルなどの有機溶媒と任意の割合で混じり合う。有機合成原料、医薬、樹脂、ゴムなどの溶剤、ゴムの加硫促進剤などに用いられる。[廣田 穰 2015年3月19日]
用途香水、香料、染料、プラスチック、合成ゴム、酢酸、そのほか種々の有機化合物の合成原料。
用途溶剤、有機合成原料。
説明Paraldehyde was first synthesized in 1829 by Wildenbusch and introduced into clinical practice in the United Kingdom by the Italian physician Vincenzo Cervello in 1882. Paraldehyde, a polymer of acetaldehyde, is a clear colorless or slightly yellow transparent liquid with a strong aromatic as well as a disagreeable taste that at low temperatures, it solidifies into a crystalline mass. This agent decomposes with strong into toxic products that may be released into water, soil, or atmosphere.
使用Paraldehyde is used as solvent for fats, oils, waxes, rubber and resins; as substitute for acetaldehyde; as intermediate for organic chemicals, dyestuffs, accelerators for vulcanizations, rubber oxidants, etc. Product Data Sheet
一般的な説明Paraldehyde is recognizable as the cyclictrimer of acetaldehyde. It is a liquid with a strong characteristicodor detectable in the expired air and an unpleasanttaste. These properties limit its use almost exclusively toan institutional setting (e.g., in the treatment of deliriumtremens). In the past, when containers were opened and airadmitted and then reclosed and allowed to stand, fatalitiesoccurred because of oxidation of paraldehyde to glacialacetic acid.
調製方法
製造方法Prepared by the polymerization of acetaldehyde catalyzed by hydrochloric acid and sulfuric acid at medium to high temperatures.
純化方法Wash paraldehyde with water and fractionally distil it. Alternatively, it is purified by drying with anhydrous Na2SO4, then cooled to 5o, and the frozen material is separated by decantation. The solid is distilled (b 121-124o/atm), the distillate is collected, stored over anhydrous Na2SO4 for several days and re-distilled at atmospheric pressure before use [Le Fevre et al. J Chem Soc 290 1950]. The 2r,4c,6t-trimethyl-1,3,5-trioxane has m 14.5o, b 125o/760mm. [Beilstein 19 II 394, 19 III/IV 4715. 19/9 V 112.]
上流・下流製品情報
上流原料
下流製品
補足説明
定義ChEBI: Paraldehyde is a trioxane that is 1,3,5-trioxane substituted by methyl groups at positions 2, 4 and 6. It has a role as a sedative.
関連反応
関連ノート
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