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PINACOLYL ALCOHOL

1. NAME
   1.1 Substance
   1.2 Group
   1.3 Synonyms
   1.4 Identification numbers
      1.4.1 CAS number
      1.4.2 Other numbers
   1.5 Main brand names, main trade names
   1.6 Main manufacturers, main importers
2. SUMMARY
   2.1 Main risks and target organs
   2.2 Summary of clinical effects
   2.3 Diagnosis
   2.4 First aid measures and management principles
3. PHYSICO-CHEMICAL PROPERTIES
   3.1 Origin of the substance
   3.2 Chemical structure
   3.3 Physical properties
      3.3.1 Colour
      3.3.2 State/form
      3.3.3 Description
   3.4 Hazardous characteristics
4. USES
   4.1 Uses
      4.1.1 Uses
      4.1.2 Description
   4.2 High risk circumstances of poisoning
   4.3 Occupationally exposed populations
5. ROUTES OF EXPOSURE
   5.1 Oral
   5.2 Inhalation
   5.3 Dermal
   5.4 Eye
   5.5 Parenteral
   5.6 Other
6. KINETICS
   6.1 Absorption by route of exposure
   6.2 Distribution by route of exposure
   6.3 Biological half-life by route of exposure
   6.4 Metabolism
   6.5 Elimination and excretion
7. TOXICOLOGY
   7.1 Mode of action
   7.2 Toxicity
      7.2.1 Human data
         7.2.1.1 Adults
         7.2.1.2 Children
      7.2.2 Relevant animal data
      7.2.3 Relevant in vitro data
      7.2.4 Workplace standards
      7.2.5 Acceptable daily intake (ADI)
   7.3 Carcinogenicity
   7.4 Teratogenicity
   7.5 Mutagenicity
   7.6 Interactions
9. CLINICAL EFFECTS
   9.1 Acute poisoning
      9.1.1 Ingestion
      9.1.2 Inhalation
      9.1.3 Skin exposure
      9.1.4 Eye contact
      9.1.5 Parenteral exposure
      9.1.6 Other
   9.2 Chronic poisoning
      9.2.1 Ingestion
      9.2.2 Inhalation
      9.2.3 Skin exposure
      9.2.4 Eye contact
      9.2.5 Parenteral exposure
      9.2.6 Other
   9.3 Course, prognosis, cause of death
   9.4 Systematic description of clinical effects
      9.4.1 Cardiovascular
      9.4.2 Respiratory
      9.4.3 Neurological
         9.4.3.1 Central nervous system (CNS)
         9.4.3.2 Peripheral nervous system (PNS)
         9.4.3.3 Autonomic nervous system (ANS)
         9.4.3.4 Skeletal and smooth muscle
      9.4.4 Gastrointestinal
      9.4.5 Hepatic
      9.4.6 Urinary
         9.4.6.1 Renal
         9.4.6.2 Other
      9.4.7 Endocrine and reproductive systems
      9.4.8 Dermatological
      9.4.9 Eye, ear, nose, throat: local effects
      9.4.10 Haematological
      9.4.11 Immunological
      9.4.12 Metabolic
         9.4.12.1 Acid-base disturbances
         9.4.12.2 Fluid and electrolyte disturbances
         9.4.12.3 Others
      9.4.13 Allergic reactions
      9.4.14 Other clinical effects
      9.4.15 Special risks
   9.5 Other
   9.6 Summary
10. MANAGEMENT
   10.1 General principles
   10.2 Life supportive procedures and symptomatic/specific treatment
   10.3 Decontamination
   10.4 Enhanced elimination
   10.5 Antidote treatment
      10.5.1 Adults
      10.5.2 Children
   10.6 Management discussion
11. ILLUSTRATIVE CASES
   11.1 Case reports from the literature
12. ADDITIONAL INFORMATION
   12.1 Specific preventative measures
   12.2 Other
13. REFERENCES

International programme on Chemical Safety

Poisons Information Monograph 981

Chemical

1. NAME

1.1 Substance

Pinacolyl Alcohol

1.2 Group

Aliphatic alcohol

1.3 Synonyms

tert-Butyl methyl carbinol; 3,3-Dimethyl-2-butanol

1.4 Identification numbers

1.4.1 CAS number

Number: 464-07-3

1.4.2 Other numbers

RTECS number: El2276000

Harmonised systems: 2905.19

EC number: 207-347-9

1.5 Main brand names, main trade names

Pinacolyl Alcohol (6CI)

1.6 Main manufacturers, main importers

Aldrich Chemical Co.

2. SUMMARY

2.1 Main risks and target organs

CNS depression and nephrotoxicity has been observed in animal studies.

2.2 Summary of clinical effects

Inhalation studies with rats have shown ataxia, mild hypoxemia, hypercapnia, and lacrimation. The Rats also showed depressed respiration and reduced motor activity upon exposure. Biochemical investigations showed increased serum cholesterol and bilirubin. Exposure effected the kidney, ureter, and bladder showing changes in the tubules including acute tubular necrosis and renal failure.

Structural similarities to ethanol suggest clinical effects may be similar ie. CNS depression, hypothermia, hypoglycemia, acidosis, electrolyte imbalances, and GI upset

2.3 Diagnosis

Diagnosis is based on history of exposure and clinical features.

2.4 First aid measures and management principles

First aid measures are similar to ethanol and other related alcohols. Treatment is mainly supportive.

3. PHYSICO-CHEMICAL PROPERTIES

3.1 Origin of the substance

Synthetic

3.2 Chemical structure

Structural formula

(CH3)3-C-CHOH-CH 3

Molecular formula; C6H14O

Molecular weight; 102.2

Structural names; 2-Butanol, 3,3-Dimethyl-; 3,3-dimethyl-2-butanol; 3.3- Dimethylbutane-2-ol.

3.3 Physical properties

3.3.1 Colour

Colourless

3.3.2 State/form

Liquid-unknown

3.3.3 Description

Boiling point = 119C to 121C

(Verschueren 1996)

Melting Point = 4.8C

(Verschueren 1996)

Specific gravity = 0.812

(Wilhoit & Zwolinski 1973)

Flash Point =28C

(Wilhoit & Zwolinski 1973)

Density at 25C g cm-3 = 0.8139

(Wilhoit & Zwolinski 1973)

Refractive Index, nD at 25C = 1.4132

(Wilhoit & Zwolinski 1973)

Heat of Vaporisation at the boiling Point: tb,C = 120.

(Wilhoit & Zwolinski 1973)

Heat of Vaporisation at the boiling Point: delta Hv kcal mol-1

(Wilhoit & Zwolinski 1973)

3.4 Hazardous characteristics

Incompatibilities:

Strong Acids

Strong Oxidising Agents

Strong Reducing Agents

Acid Chlorides

Acid Anhydrides

Phosphorous Halides (Aldrich Chemical Co. 1998)

Hazardous combustion or decomposition. When heated to decomposition it emits acrid smoke and irritating vapours (Lewis. 1996), products with toxic fumes of carbon monoxide, carbon dioxide (Aldrich Chemical Co. 1998)

4. USES

4.1 Uses

4.1.1 Uses

4.1.2 Description

Precursor to chemical warfare agents (such as Soman)

4.2 High risk circumstances of poisoning

Possibility of exposure to workers during manufacture, formulation, packing, transport, and storage, therefore exposure will be primarily through inhalation or eye contact though dermal adsorption is possible.

4.3 Occupationally exposed populations

Manufacturing plant operators

5. ROUTES OF EXPOSURE

5.1 Oral

No data available for human absorption. (physio-chemical relationship to ethanol and related alcohols suggest it would be absorbed by this route.).

5.2 Inhalation

Absorption through pulmonary epithelium and mucous membranes of the respiratory tract. Shown in rats (James et al, 1987).

5.3 Dermal

No data available.

5.4 Eye

No data available.

5.5 Parenteral

No data available.

5.6 Other

No data available.

6. KINETICS

6.1 Absorption by route of exposure

No data available.

6.2 Distribution by route of exposure

No data available.

6.3 Biological half-life by route of exposure

No data available.

6.4 Metabolism

No human data available. In rats it is suggested that pinacolyl alcohol is metabolised by alcohol dehydrogenase with the major metabolite being pinacolone (James et al, 1987).

6.5 Elimination and excretion

No human data available. In rats it is metabolised to pinacolone which is then exhaled (James et al, 1987).

7. TOXICOLOGY

7.1 Mode of action

No data available, but expected to be similar to ethanol and related alcohols.

7.2 Toxicity

7.2.1 Human data

7.2.1.1 Adults

No data available.

7.2.1.2 Children

No data available.

7.2.2 Relevant animal data

LCLo Rat inhalation 3600 ppm / 2.3 H (James et al, 1987).

Rats showed behavioural effects - ataxia, exposure to 5 mg/l for 5 H causes mild hypoxemia and hypercapnia (James et al, 1987).

TCLo Rat 4930 mg/m3 for 6 hour exposure period per day for 13 week inhalation study (James et al, 1987). Clinical signs related to exposure were alopecia, ataxia and lacrimation. Suggested difference in sex susceptibility

No observed effect level male rat 0.2 mg/l

No observed effect level female rat 1.0 mg/l

Rats showed depressed respiration and reduced motor activity upon exposure. Blood levels showed increased serum cholesterol and bilirubin. Exposure affected the kidney, ureter, and bladder showing changes in the tubules including acute renal failure and acute tubular necrosis. Suggested possibility of changes in ovarian weight.

7.2.3 Relevant in vitro data

No data available

7.2.4 Workplace standards

No data available.

7.2.5 Acceptable daily intake (ADI)

No data available.

7.3 Carcinogenicity

No data available.

7.4 Teratogenicity

No data available.

7.5 Mutagenicity

No data available.

7.6 Interactions

No data available.

8. TOXICOLOGICAL ANALYSES AND
BIOMEDICAL INVESTIGATIONS

9. CLINICAL EFFECTS

9.1 Acute poisoning

9.1.1 Ingestion

No data available.

9.1.2 Inhalation

No data available. Rat data showed ataxia, also mild hypoxemia and hypercapnia(James et al, 1987).. These signs indicate some similar effects as those with ethanol exposure.

9.1.3 Skin exposure

No data available.

9.1.4 Eye contact

No data available.

9.1.5 Parenteral exposure

No data available.

9.1.6 Other

No data available.

9.2 Chronic poisoning

9.2.1 Ingestion

No data available.

9.2.2 Inhalation

No data available. Rat data showed alopecia, ataxia and lacrimation as well as depressed respiration and reduced motor activity for chronic exposure 6 hours a day over a 13 week period by inhalation (James et al, 1987).

9.2.3 Skin exposure

No data available.

9.2.4 Eye contact

No data available.

9.2.5 Parenteral exposure

No data available.

9.2.6 Other

No data available.

9.3 Course, prognosis, cause of death

No data available.

9.4 Systematic description of clinical effects

9.4.1 Cardiovascular

No data available.

9.4.2 Respiratory

No human data available. Rats showed depressed respiration with chronic inhalational exposure.

9.4.3 Neurological

9.4.3.1 Central nervous system (CNS)

No human data available. Rat studies shown to have similar effects to ethanol on the CNS, ataxia, and CNS depression (James et al 1987).

9.4.3.2 Peripheral nervous system (PNS)

No data available.

9.4.3.3 Autonomic nervous system (ANS)

No data available.

9.4.3.4 Skeletal and smooth muscle

No data available.

9.4.4 Gastrointestinal

No data available.

9.4.5 Hepatic

No data available.

9.4.6 Urinary

9.4.6.1 Renal

No human data available. Rat data showed the kidney, ureter, and bladder to be effected, changes in the tubules including acute renal failure and acute tubular necrosis in some cases (James et al, 1987).

9.4.6.2 Other

No data available.

9.4.7 Endocrine and reproductive systems

No data available.

9.4.8 Dermatological

No data available.

9.4.9 Eye, ear, nose, throat: local effects

No data available.

9.4.10 Haematological

No data available.

9.4.11 Immunological

No data available.

9.4.12 Metabolic

9.4.12.1 Acid-base disturbances

No data available.

9.4.12.2 Fluid and electrolyte disturbances

No data available.

9.4.12.3 Others

No data available.

9.4.13 Allergic reactions

No data available.

9.4.14 Other clinical effects

No data available.

9.4.15 Special risks

No data available.

9.5 Other

No data available. Due to similarity to ethanol similar effects may occur i.e. CNS depression, hypothermia, hypoglycemia, acidosis, electrolyte imbalances, and GI upset (see Intox PIM for ethanol).

9.6 Summary

10. MANAGEMENT

10.1 General principles

No data available. Similarity to ethanol in effects for inhalation would suggest some of the ethanol management principles could be applied. Assess airways, breathing and circulation and provide support if necessary. Decontaminate by removing contaminated clothing. Monitor fluid/electrolytes, glucose and airway management. Avoid aspiration of vomitus.

10.2 Life supportive procedures and symptomatic/specific treatment

Assess airways breathing and circulation and support if necessary.

10.3 Decontamination

No data available.

10.4 Enhanced elimination

No data available.

10.5 Antidote treatment

10.5.1 Adults

No data available.

10.5.2 Children

No data available.

10.6 Management discussion

11. ILLUSTRATIVE CASES

11.1 Case reports from the literature

No data available.

12. ADDITIONAL INFORMATION

12.1 Specific preventative measures

12.2 Other

13. REFERENCES

Aldrich Chemical Co. Material Safety Data Sheet - 3,3-dimethyl-2-butanol. 1998

Intox CD Rom (2001) Ethanol PIM.

James JT, Armstrong RD, Leach G, Farrand RL, Burnett D, Englee MJ & Hall WC (1987) A 13-week vapour study of 3,3-dimethyl-2-butanol in sprague-dawley rats. Journal of Applied Toxicology, 7(2): 135-142

James JT, Infiesto BP & Landauer MR (1987) Acute inhalation Toxicity of 3,3-dimethyl-2-butanol in sprague dawley rats. Journal of Applied Toxicology, 7(5): 307-312

Lewis JR,SR. (1996) Sax's Dangerous Properties of industrial materials, ninth edition. Van Nostrand Reinhold an International Thomson Publishing company

Verchueren K (1996) Handbook of environmental data on organic chemicals, 3rd ed. Van Nostrand Reinhold an International Thomson Publishing company

Wilhoit RC & Zwolinski BJ ed. (1973) Physical and Thermodynamic Properties of Aliphatic Alcohols. Journal of Physical and Chemical Reference data Vol 2, Supplement No.1

14. AUTHOR(S), REVIEWER(S), DATE(S)
(INCLUDING UPDATES), COMPLETE ADDRESS(ES)

Daniel W Moore
Department of Pharmacology and Toxicology
University of Otago
P. O. Box 913
Dunedin
New Zealand

PEER REVIEWED GROUP

Ligia Fruchtengarten, Mahdi Balali-Mood, Wayne Temple, Nigel Langford
Edinburgh September 2001



    See Also:
       Toxicological Abbreviations