2,4,6-Trimethyl-1,3,5-trioxan

Paraldehyde

HCID 31264CAS 123-63-7

Grundinformationen

Standard-SMILES
CC1OC(C)OC(C)O1
InChIKey
SQYNKIJPMDEDEG-UHFFFAOYSA-N
Summenformel
C6H12O3
Durchschnittliche Molmasse
132,16 g/mol
Monoisotopische Masse
132,07864424

Namen und Bezeichner

Bevorzugter Name
Paraldehyde
IUPAC
2,4,6-trimethyl-1,3,5-trioxane
Lokaler Name
2,4,6-Trimethyl-1,3,5-trioxan
Englischer Name
Paraldehyde
Summenformel
C6H12O3
Molmasse
132.16

Namen und Synonyme

PARALDEHYDE2,4,6-Trimethyl-1,3,5-trioxane123-63-7ParacetaldehydeParalParaldehydParaacetaldehydeTriacetaldehydeElaldehydeParaldeidep-Acetaldehyde1,3,5-Trioxane, 2,4,6-trimethyl-
Weitere Namen anzeigen
ALDEHYDEETHYL ALDEHYDEACETIC ALDEHYDEFEMA 2003trimeric acetaldehydePcho
Acetaldehyde, trimer1,3,5-Trimethyl-2,4,6-trioxane2,4,6-Trimethyl-1,3,5-trioxacyclohexaneDTXSID9023419Paraldehyde Enema (BPC 1973)Paraldehyde (USP)Paraldehyde Draught (BPC 1973)2,4,6-Trimethyl-1,3,5-trioxaan

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,7
Polarare Oberfläche (TPSA)
27,7 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
9

Experimentelle und physikochemische Eigenschaften

LogP · 4 Einträge

0.73

Log Kow = 0.67

0.67

0.67

Odor · 2 Einträge

CHARACTERISTIC AROMATIC ODOR

Agreeable odor

Taste · 2 Einträge

DISAGREEABLE TASTE

Burning taste

Density · 5 Einträge

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

Viscosity1.128 centipoise at 70 °F
Color/FormCOLORLESS, TRANSPARENT LIQUID

Physikochemische Eigenschaften

Schmelzpunkt
12 °C · 12 °C
Siedepunkt
65 · 65-82 °C
Dichte
0.994 g/mL · 0.994 g/mL at 20 °C (lit.)
Dampfdichte
1.52 · 1.52 (vs air)
Dampfdruck
25.89 psi · 25.89 psi ( 55 °C)
Brechungsindex
20 · n20/D 1.39

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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.

Gefahrenhinweise

Regulatory Information · 6 Einträge

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.)

DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

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 · 2 Einträge

DANGEROUS, WHEN EXPOSED TO HEAT, FLAME OR OXIDIZERS.

FLAMMABLE LIQUID.

Health Hazards · 2 Einträge

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.

Hazards SummaryA skin, eye, and respiratory tract irritant; Causes sedation and respiratory depression when ingested; May cause injury to the liver and kidneys; [ICSC] A severe eye irritant; Targets CNS, heart, lungs, liver, and kidneys; [MSDSonline]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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 · 4 Einträge

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 · 2 Einträge

· 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 · 2 Einträge

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.

Safe StorageFireproof. Separated from food and feedstuffs, bases and oxidants.
Firefighting HazardsVapors are heavier than air and may travel to a source of ignition and flash back.

Toxikologische Informationen

Interactions · 5 Einträge

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 · 3 Einträge

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).

Food Survey ValuesIdentified as a volatile flavor component of fried bacon(1).
Adverse EffectsNeurotoxin - Other CNS neurotoxin;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Signs and Symptoms · 4 Einträge

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.

Regulatorische Informationen

Regulatory Information · 6 Einträge

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 · 3 Einträge

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 · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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).

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 1264
hs_code
29125000
RTECS-Nr.
YK0525000
risk_code
11-R11-10

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

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

PharmacodynamicsParaldehyde blocks neuromuscular transmission.
Mechanism of Action · 2 Einträge

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 · 2 Einträge

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 · 2 Einträge

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 · 2 Einträge

Drugs used to prevent SEIZURES or reduce their severity.

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.

Verwendung und Herstellung

Uses · 6 Einträge

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 · 2 Einträge

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 · 5 Einträge

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 · 4 Einträge

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Environmental transformation -> Pesticide transformation products (metabolite, successor)

General Manufacturing Information · 2 Einträge

1,3,5-Trioxane, 2,4,6-trimethyl-: ACTIVE

/Paraldehyde is/ a cyclic polymer (trimer) of acetaldehyde.

Anwendungen · 2 Einträge

BeschreibungParaldehyde 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.

VerwendenParaldehyde 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

Darstellung

synthetischePrepared by the polymerization of acetaldehyde catalyzed by hydrochloric acid and sulfuric acid at medium to high temperatures.

Ergänzende Hinweise

DefinitionChEBI: 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.

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