Tert-Amyl alcohol: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
Line 119: Line 119:
===Routes of administration===
===Routes of administration===
''t''-AmOH is one of few alcohols potent enough for practical use with the forms described below, as well as conventional administration routes.
''t''-AmOH is one of few alcohols potent enough for practical use with the forms described below, as well as conventional administration routes.

In [[state of matter]], ''t''-Amylol powder can be used by three of the four fundamental states for different [[routes of administration]]; Solid (oral capsules), liquid (mixed to alcohol drinks, or intravenous therapy (as already demonstrated in animal models<ref>https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6405#x332</ref>), and gas (distilled water solution turned to aerosolization for inhalation with a [[nebulizer]]<ref>https://www.ncbi.nlm.nih.gov/pubmed/17089700</ref>). ''t''-Amylol powder compared to ethanol powder will provide minimal energy intake (e.g. 1 gram instead of 20). Additionally, when used with [[time release technology]] [[dosage form]] (e.g. a few small-sized capsules with different time-release), ''t''-Amylol powder can provide low-dose alcohol therapy to eliminate alcohol intoxication, lower the risk for [[alcohol dependency]], and yet provide its health effects.


===Oral===
===Oral===

Revision as of 07:00, 7 February 2013

2-Methyl-2-butanol
Stereo, skeletal formula of 2-methyl-2-butanol
Ball-and-stick model of 2-methyl-2-butanol
Names
Preferred IUPAC name
2-Methyl-2-butanol[1]
Systematic IUPAC name
2-Methylbutan-2-ol[1]
Other names
tert-Amyl alcohol[1]

t-Amylol
Amylene hydrate[1]
Dimethylethylcarbinol[1]

tert-Pentyl alcohol[1]
Identifiers
3D model (JSmol)
1361351
ChEMBL
ChemSpider
ECHA InfoCard 100.000.827 Edit this at Wikidata
EC Number
  • 200-908-9
KEGG
MeSH tert-amyl+alcohol
RTECS number
  • SC0175000
UNII
UN number 1105
  • InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3 checkY
    Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N checkY
  • CCC(C)(C)O
Properties
C5H12O
Molar mass 88.150 g·mol−1
Appearance Colourless liquid
Odor Camphorous
Density 805 mg cm−3
Melting point −9 °C; 16 °F; 264 K
120 g dm−3
log P 1.095
Vapor pressure 1.6 kPa (at 20 °C)
1.405
Thermochemistry
229.3 J K−1 mol−1
−380.0–−379.0 kJ mol−1
−3.3036–−3.3026 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H315, H332, H335
P210, P261
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point 19 °C
Explosive limits 9%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

tert-Amyl alcohol (t-Amylol, t-AmOH, TAA), also known as 2-methyl-2-butanol (2M2B), is one of the alcohols found in alcoholic beverages in small quantities. It is extremely potent compared with ethanol and has no toxic aldehyde metabolites because it is an tertiary alcohol, so does not cause a hangover. It is a colorless liquid with characteristic odor of camphor, and have a burning taste. TAA compared ethanol will provide minimal energy intake (e.g. 1 gram instead of 20). Additionally, when used with time release technology dosage form (e.g. a few small-sized capsules with different time-release), t-Amylol powder can provide low-dose alcohol therapy to eliminate alcohol intoxication, lower the risk for alcohol dependency, and yet provide its health effects

History

Archaeological record

tert-Amyl alcohol is found in beer (0.7%) and other alcoholic beverages.[citation needed] Chemical tests of ancient pottery jars reveal that beer was produced about 3,500 BC in what is today Iran, and was one of the first-known biological engineering tasks where the biological process of fermentation is used. Also recent archaeological findings showing that Chinese villagers were brewing fermented alcoholic drinks as far back as 7000 BC on small and individual scale, with the production process and methods similar to that of ancient Egypt and Mesopotamia.[2] This indicates that t-Amylol has been partially responsible for alcohol intoxication for thousands of years.

Chemistry

t-AmOH is one of the isomers of amyl alcohol. It is not expected to be susceptible to direct photolysis by sunlight.[3] Tertiary alcohols cannot be oxidised which makes them useful as drugs because they do not form toxic aldehyde and carboxylic acid metabolites.[4]

Pharmaceutical research

A US patent has been registered for the alcohol powder process as early as 1974.[5]

A meta-analysis found with data from 477,200 individuals determined the dose-response relationships by sex and end point using lifetime abstainers as the reference group. The search revealed 20 cohort studies that met our inclusion criteria. A U-shaped relationship was found for both sexes. Compared with lifetime abstainers, the relative risk (RR) for type 2 diabetes among men was most protective when consuming 22 g/day alcohol (RR 0.87 [95% CI 0.76–1.00]) and became deleterious at just over 60 g/day alcohol (1.01 [0.71–1.44]). Among women, consumption of 24 g/day alcohol was most protective (0.60 [0.52–0.69]) and became deleterious at about 50 g/day alcohol (1.02 [0.83–1.26]).[6]

Ethanol has been found to double the lifespans of worms feed 0.005% ethanol but does not markedly increase at higher concentrations. Supplementing starved cultures with n-propanol and n-butanol also extended lifespan.[7] However, this seems to be statistically significant for humans when compared to the previous study discusses; Human macronutrients in food consist mainly of water and the Dietary Reference Intake (DRI) for water is 3.7 litres (3700 mL x 0.005% EtOH = 18.5 mL EtOH) for 19-70 year old males, and 2.7 litres (2700 mL x 0.005% EtOH = 13.5 mL) for 19-70 year old women.

Also, propanol have been used in higher doses (recreationally) by humans with less side-effects than ethanol, like less hangover. t-Amylol have a history of human use, and despite being 20 x more potent than EtOH, a therapeutic index of 2.8 that of ethanol (potency compared to EtOH/(EtOH LD50/t-AmOH LD50[8] ratio) = 20/(7060/1000) = 2.8) oral in rat. If t-Amylol shows promising results when fed to Caenorhabditis elegans worms it may have the same benefits to humans. There are no such studies reported to date.

Industrial production

The oxo process is the principal one in practice today; only minor quantities, mainly in Europe are obtained from separation of fusel oil. tert-Amyl alcohol is produced on a commercial scale in lower volume by hydration of amylenes.[9]

Occurrence

Alcoholic beverages

t-AmOH is a fusel alcohol of the fermentation of grain[10] so it is occurring in most alcoholic beverages, especially found in beer.

Natural sources

t-AmOH has been identified as a volatile in cassava[11] and fried bacon[12] suggesting that it may be a naturally-occurring chemical.

Modern usage

Tertiary alcohols like t-AmOH does not produce toxic metabolites.[4][13] As a result of this it has been used recreationally, with the earliest reported instance on a message board occurred in May 2009.[14][15]

Routes of administration

t-AmOH is one of few alcohols potent enough for practical use with the forms described below, as well as conventional administration routes.

In state of matter, t-Amylol powder can be used by three of the four fundamental states for different routes of administration; Solid (oral capsules), liquid (mixed to alcohol drinks, or intravenous therapy (as already demonstrated in animal models[16]), and gas (distilled water solution turned to aerosolization for inhalation with a nebulizer[17]). t-Amylol powder compared to ethanol powder will provide minimal energy intake (e.g. 1 gram instead of 20). Additionally, when used with time release technology dosage form (e.g. a few small-sized capsules with different time-release), t-Amylol powder can provide low-dose alcohol therapy to eliminate alcohol intoxication, lower the risk for alcohol dependency, and yet provide its health effects.

Oral

Molecular encapsulation

Main article: Alcohol powder

According to food chemist Pollmer of the European Institute of Food and Nutrition Sciences in Munich, alcohol can molecular encapsulated in cyclodextrins, a sugar derivative. In this way, encapsulated in small rings, the fluid can be handled as a powder. The cyclodextrins can absorb an estimated 60 percent of their own weight in alcohol.[18] A US patent was registered for the process as early as 1974.[5]

Gelatin capsules

tert-amyl alcohol can be placed into gelatin capsules as a liquid or cyclodextrin complexed powder to avoid an unpleasant taste.

Inhalation

Although not documented, it is possible, as with any volatile compound.

Nebulization

A nebulizer device that vaporizes liquor (distilled spirits) and mixes it with oxygen into small aerosol droplets can be used to administer cyclodextrin encapsulated TAA[19] so that it can be more easily inhaled into the lungs than the ordinarily harsh vapours.

Injection

TAA has been administered intravenously to treat methanol poisoning in dogs.[20] Its mechanism is the same as that of ethanol in methanol poisoning; it blocks acetaldehyde dehydrogenase to prevent oxidation of methanol.

Pharmacology

In humans it possesses euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation, and was previously used in medicine for this purpose.[21] It is active in doses of 2,000-4,000 mg, making it nearly as potent as GHB. Its hypnotic potency is between that of chloral hydrate and paraldehyde[22] or between benzodiazepines and ethanol. In humans, 2-methyl-2-butanol is metabolized primarily via gluconoridation and oxidation to 2,3-dihydroxy-2-methylbutane.[13] Overdose produces symptoms similar to alcohol poisoning and is a medical emergency.

The effect of tert-Amyl alcohol and related compounds on ligand binding to the γ-aminobutyric acidA (GABAA) receptor in rat brain membranes has been investigated.[23]

Comparison with ethanol

  • It is active in doses of 2,000-4,000 mg making it some 20 times more potent than regular ethanol[24][25]
  • The unavoidable metabolism of ethanol into ethanal, a toxic aldehyde is responsible for a significant portion of the chronic toxicity and hangover. Tertiary alcohols are unable to be metabolised into aldehydes[13] and as a result they cause no hangover or toxicity through this mechanism.

Case reports of acute intoxication

  • 18 g: Ingestion of 18 g of 2-methyl-2-butanol by an adult resulted in unconsciousness, a deep sleep lasting more than one day, and a slow recovery.
  • 27 g: The ingestion of 27 g of 2-methyl-2-butanol by an adult female resulted in unconsciousness within 0.5 hr, marked signs of intoxication through the following day, and complete recovery after 14 days.
  • 29 g rectally: The administration of an enema of approximately 29 g of 2-methyl-2-butanol to an adult male resulted in death after 53 hr, but the case was complicated by concurrent pneumonia in the patient.[26]
  • The oral LD50 in rats is 1000 mg/kg.[8] The subcutaneous LD50 in mice is 2100 mg/kg [27]

See also

References

  1. ^ a b c d e f "tert-Amyl alcohol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 2011-12-13.
  2. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1073/pnas.0407921102 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1073/pnas.0407921102 instead.
  3. ^ http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~PghGgW:1:fate
  4. ^ a b Carey, Francis. Organic Chemistry (4 ed.). ISBN 0072905018. Retrieved 2013-02-05.
  5. ^ a b Preparation of an Alcohol Containing Powder, General Foods Corporation March 31, 1972
  6. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.2337/dc09-0227, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.2337/dc09-0227 instead.
  7. ^ Castro PV, Khare S, Young BD, Clarke SG. "Caenorhabditis elegans Battling Starvation Stress: Low Levels of Ethanol Prolong Lifespan in L1 Larvae." PLoS ONE 7(1), 18th January 2012.
  8. ^ a b Template:Cite PMID
  9. ^ Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V2: 716. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005
  10. ^ George Milbry Gould & R J E Scott. "The Practitioner's Medical Dictionary", 1910
  11. ^ Dougan J; Robinson, Janet M.; Sumar, Salim; Howard, George E.; Coursey, D. G.; et al. (1983). "Some flavouring constituents of cassava and of processed cassava products". J Sci Food Agric. 34 (8): 874–84. doi:10.1002/jsfa.2740340816. {{cite journal}}: Explicit use of et al. in: |author= (help)
  12. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1021/jf00116a038, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1021/jf00116a038 instead.
  13. ^ a b c Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 10367338 , please use {{cite journal}} with |pmid= 10367338 instead.
  14. ^ "2-methyl-2-butanol - First Time - Nice, Euphoric Sedative, Few Negatives". Retrieved 2013-01-13.
  15. ^ "2-methyl-2-butanol "Vodka"". Retrieved 2013-01-13.
  16. ^ https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6405#x332
  17. ^ https://www.ncbi.nlm.nih.gov/pubmed/17089700
  18. ^ Alcohol powder: Alcopops from a bag, Westdeutsche Zeitung, 28 October 2004 (German)
  19. ^ Template:Cite PMID
  20. ^ Bingham, E. Patty's Toxicology. Vol. 6. New York. p. 437. ISBN 978047123166. Retrieved 2013-02-05. {{cite book}}: Check |isbn= value: length (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  21. ^ Robert A. Lewis (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 45. ISBN 1-56670-223-2.
  22. ^ F. A. Castle & C. Rice (1888). "Amylene and amylene hydrate". The American Druggist. 17 (3): 58–59. {{cite journal}}: Unknown parameter |month= ignored (help)
  23. ^ Template:Cite DOI
  24. ^ Hans Brandenberger & Robert A. A. Maes, ed. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. p. 401. ISBN 3-11-010731-7.
  25. ^ D. W. Yandell; et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News. 5. Lousville KY: John P. Morton & Co: 88–89. {{cite journal}}: Explicit use of et al. in: |author= (help)
  26. ^ "2-Methyl-2-Butanol". Toxicology Data Network. National Institutes of Health.
  27. ^ Template:Cite PMID
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tert-Amyl_alcohol&oldid=537012786"