2-Methyl-2-butanol

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2-Methyl-2-butanol

Preferred IUPAC name 2-Methyl-2-butanol^{[citation needed]}
Systematic name 2-Methylbutan-2-ol^[1]
Other names tert-Amyl alcohol^{[citation needed]} Amylene hydrate^{[citation needed]} Dimethylethylcarbinol^{[citation needed]} tert-Pentyl alcohol^{[citation needed]}
Identifiers
CAS number	75-85-4^Y
PubChem	6405
ChemSpider	6165^Y
UNII	69C393R11Z^Y
EC number	200-908-9
UN number	1105
KEGG	D02931^N
MeSH	tert-amyl+alcohol
ChEMBL	CHEMBL44658^Y
RTECS number	SC0175000
Beilstein Reference	1361351
Jmol-3D images	Image 1
SMILES CCC(C)(C)O
InChI InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3^Y Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N^Y
Properties
Molecular formula	C₅H₁₂O
Molar mass	88.15 g mol⁻¹
Exact mass	88.088815006 g mol⁻¹
Appearance	Colourless liquid
Odor	Camphorous, peppermint
Density	805 mg cm⁻³
Melting point	-9 °C, 264 K, 16 °F
Boiling point	101-103 °C, 374-376 K, 214-217 °F
Solubility in water	120 g dm⁻³
log P	1.095
Vapor pressure	1.6 kPa (at 20 °C)
Refractive index (n_D)	1.405
Thermochemistry
Std enthalpy of formation Δ_fH^o₂₉₈	−380.0–−379.0 kJ mol⁻¹
Std enthalpy of combustion Δ_cH^o₂₉₈	−3.3036–−3.3026 MJ mol⁻¹
Standard molar entropy S^o₂₉₈	229.3 J K⁻¹ mol⁻¹
Hazards
MSDS	hazard.com
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H315, H332, H335
GHS precautionary statements	P210, P261
EU Index	603-007-00-2
EU classification	F Xn
R-phrases	R11, R20, R37/38
S-phrases	(S2), S46
NFPA 704	3 1 0
Flash point	19 °C
Autoignition temperature	437 °C
Explosive limits	9%
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2-Methyl-2-butanol, also known as tert-amyl alcohol, 2M2B or amylene hydrate, is one of the isomers of amyl alcohol. It is a clear, colorless liquid with a strong odor of peppermint or camphor.^[2]^[3] In humans it possesses sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation, and was previously used in medicine for this purpose.^[4] It is active in doses of 2,000-4,000 mg, making it some 20 times more potent than regular ethanol.^[5]^[6] Its hypnotic potency is between that of chloral hydrate and paraldehyde.^[7] In humans, 2-methyl-2-butanol is metabolized primarily via gluconoridation and oxidation to 2,3-dihydroxy-2-methylbutane.^[8] Overdose produces symptoms similar to alcohol poisoning and is a medical emergency.

References

^ "tert-amyl alcohol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6405&loc=ec_rcs. Retrieved 2011-12-13.
^ Coblentz, Virgil (1899). The Newer Remedies: A reference manual for physicians, pharmacists, and students (3rd ed.). Philadelphia: P. Blakiston's Son & Co. p. 18. http://books.google.com/books?id=BRxKAAAAMAAJ&pg=PA18#v=onepage&q&f=false.
^ H. C. Wood & R. M. Smith, ed. (15 September 1887). "Amylene hydrate - a new hypnotic". Therapeutic Gazette - A monthly journal of physiological and clinical therapeutics (Detroit MI and Philadelpia PA: G. S. Davis) 3: 605–606. http://books.google.com/books?id=bKICAAAAYAAJ&pg=PA605#v=onepage&q&f=false.
^ Robert A. Lewis (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 45. ISBN 1-56670-223-2. http://books.google.com/books?id=zGbVfBItUwcC&pg=PA45#v=onepage&q&f=false.
^ Hans Brandenberger & Robert A. A. Maes, ed. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. p. 401. ISBN 3-11-010731-7. http://books.google.com/books?id=ZhYtynyC4kAC&pg=PA401#v=onepage&q&f=false.
^ D. W. Yandell et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News (Lousville KY: John P. Morton & Co) 5: 88–89. http://books.google.com/books?id=Ra5YAAAAMAAJ&pg=PA88#v=onepage.
^ F. A. Castle & C. Rice (March 1888). "Amylene and amylene hydrate". The American Druggist 17 (3): 58–59. http://books.google.com/books?id=gNIAAAAAYAAJ&pg=PA58#v=onepage&q&f=false.
^ Collins, A. S.; Sumner, S. C.; Borghoff, S. J.; Medinsky, M. A. (1999). "A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures". Toxicological sciences : an official journal of the Society of Toxicology 49 (1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338. edit

v t e Hypnotics/sedatives (N05C)

GABA_A agonists/PAMs	Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarb • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenobarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lorazepam •Lormetazepam • Midazolam • Nimetazepam • Nitrazepam • Quazepam • Temazepam • Triazolam Carbamates: Carisoprodol • Ethinamate • Hexapropymate • Meprobamate • Methocarbamol • Procymate • Tybamate Neuroactive Steroids: Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Eltanolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • Org 21465 • Tetrahydrodeoxycorticosterone Nonbenzodiazepines: CL-218,872 • Eszopiclone • Indiplon • JM-1232 • Lirequinil • Necopidem • Pazinaclone • ROD-188 • Saripidem • Suproclone • Suriclone • SX-3228 • U-89843A • U-90042 • Zaleplon • Zolpidem • Zopiclone Phenols: Fospropofol • Propofol Piperidinediones: Glutethimide • Methyprylon • Pyrithyldione • Piperidione Quinazolinones: Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone • Nitromethaqualone Volatiles/gases: 2-Methyl-2-butanol • Acetophenone • Acetylglycinamide chloral hydrate • Centalun • Chloral hydrate • Ethanol (Alcohol) • Paraldehyde • Trichloroethanol Others: Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralose • Chloralodol • Clomethiazole • Dichloralphenazone • Ethchlorvynol • Etomidate • Gaboxadol • Loreclezole • Methylpentynol • Metomidate • Org 25435 • Petrichloral • Sulfonmethane • Triclofos • Valerenic acid (Valerian)

GABA_B agonists	1,4-Butanediol • Aceburic acid • GABOB • GHB (Sodium oxybate) • GBL • GVL

H₁ inverse agonists	Antihistamines: Captodiame • Cyproheptadine • Diphenhydramine • Doxylamine • Hydroxyzine • Methapyrilene • Pheniramine • Promethazine • Propiomazine Antidepressants: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)

α₁-Adrenergic antagonists	Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Niaprazine

α₂-Adrenergic agonists	4-NEMD • Clonidine • Detomidine • Dexmedetomidine • Lofexidine • Medetomidine • Romifidine • Tizanidine • Xylazine

5-HT_2A antagonists	Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Eplivanserin • Niaprazine • Pruvanserin • Volinanserin

Melatonin agonists	Agomelatine • LY-156,735 • Melatonin • Ramelteon • Tasimelteon

Orexin antagonists	Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant • TCS-OX2-29

Others	Acecarbromal • Apronal • Bromisoval • Cannabidiol (Cannabis) • Carbromal • Embutramide • Evoxine • Fenadiazole • Gabapentin • Kavalactones (Kava) • Mephenoxalone • Opioids (Oxycodone, Morphine (Opium), etc.) • Passion flower • Scopolamine (Mandrake) • Valnoctamide

GABAergics

Receptor
ligands

GABA_A	Agonists: Main site: Bamaluzole Gaboxadol Ibotenic acid Isoguvacine Isonipecotic acid Muscimol (Amanita Muscaria) Progabide SL 75102 Thiomuscimol Tolgabide; Positive allosteric modulators: Barbiturates Benzodiazepines Carbamates Chlormezanone Clomethiazole Ethanol (Alcohol) Etomidate Kavalactones (Kava) Loreclezole Metomidate Neuroactive steroids Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) Phenols Piperidinediones Propanidid Pyrazolopyridines Quinazolinones ROD-188 Skullcap Stiripentol Valerenic acid (Valerian) * See the GABA_A receptor PAMs navbox for a full list of GABA_A positive allosteric modulators. Antagonists: Main site: Bicuculline Gabazine Pitrazepin Quisqualamine; Negative allosteric modulators: α5IA Bilobalide Cicutoxin Cyclothiazide DMCM Flumazenil Flurothyl Furosemide L-655,708 Oenanthotoxin Penicillin Pentylenetetrazol Picrotoxin PWZ-029 Ro15-4513 Sarmazenil Suritozole Thujone (Absinthe) Thiocolchicoside ZK-93426

GABA_B	Agonists: Main site: 1,4-Butanediol Baclofen GBL GHB GHV GVL Lesogaberan Phenibut Progabide SKF-97,541 Tolgabide; Positive allosteric modulators: BHF-177 BHFF BSPP CGP-7930 GS-39783 Antagonists: Main site: CGP-35348 Phaclofen Saclofen SCH-50911

GABA_C	Agonists: Main site: CACA CAMP GABOB N(4)-chloroacetylcytosine arabinoside Progabide Tolgabide Antagonists: Main site: Bilobalide TPMPA

Reuptake
inhibitors

Plasmalemmal

GAT inhibitors	CI-966 Deramciclane EF-1502 Gabaculine Guvacine Nipecotic acid NNC 05-2090 SKF-89976A SNAP-5114 Tiagabine

Enzyme
inhibitors

Anabolism

GAD inhibitors	Allylglycine

Catabolism

GABA-T inhibitors	3-Hydrazinopropionic acid Aminooxyacetic acid Gabaculine Isoniazid Phenelzine Phenylethylidenehydrazine Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (Divalproex sodium) Valproic acid Valpromide Vigabatrin

Others

Precursors	Glutamate Glutamine

Cofactors	Vitamin B6 (pyridoxine pyridoxamine pyridoxal phosphate)

Others	Gabapentin L-Theanine Picamilon Pregabalin

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Is 2-methyl-2-butanol a tertiary alcohol?

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