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Comparison of psychoactive alcohols in alcoholic drinks

From Wikipedia - Reading time: 3 min

Photo: negative (left) with ethanol and positive with t-butanol.

Comparison of psychoactive alcohols in alcoholic beverages.

The Lucas test in alcohols is a test to differentiate between primary, secondary, and tertiary alcohols.

General

[edit]
IUPAC name Common name Classification CAS
Ethanol Alcohol, drinking alcohol, ethyl alcohol, EtOH Primary 64-17-5
Propan-1-ol 1-Propanol, 1-propyl alcohol, PrOH Primary 71-23-8
2-(1H-Indol-3-yl)ethanol Tryptophol Primary 526-55-6
2-Methylbutan-1-ol 2-Methyl-1-butanol (2M1B) Secondary 137-32-6
2-methylpropan-1-ol 2-Methyl-1-propanol (2M1P), Isobutanol Primary 78-83-1
2-Methylbutan-2-ol 2-Methyl-2-butanol (2M2B), tert-Amyl alcohol (TAA, tert-amylol) Tertiary 75-85-4
2-Methylpropan-2-ol 2-Methyl-2-propanol (2M2P), tert-Butyl alcohol ((TBA), tert-butanol), t-BuOH Tertiary 75-65-0
2-Phenylethan-1-ol Phenethyl alcohol, 2-Phenylethanol Primary 60-12-8
3-Methylbutan-1-ol 3-methyl-1-butanol (3M1B), isoamyl alcohol, isopentyl alcohol (isopentanol) Primary 123-51-3

Pharmacology

[edit]
IUPAC name IARC carcinogen group Toxic metabolite(s) Alcohol by volume (ABV)[1] LD50 in rat, oral[2]
Ethanol Group 1 Acetaldehyde → acetic acid Up to 95.6% in rectified spirit 7060 mg/kg
Propan-1-ol Propionaldehyde → propionic acid 2.8% (mean) in Jamaican rum: 2384–3130 mg/100 mL. Up to 3500 mg/L (0.35%) in spirits.[3] 1870 mg/kg
2-(1H-Indol-3-yl)ethanol ? ? ?
2-Methylbutan-1-ol ? 1.2% (mean) in Bourbon: 910–1390 mg/100 mL 4170 mg/kg[4]
2-methylpropan-1-ol ? 0.9% (mean) in Rye mash cistern room: 534–1197 mg/100 mL 2460 mg/kg
2-Methylbutan-2-ol None (tertiary alcohol) 0.07% in beer: 70 mg/100 mL (see tert-Pentyl alcohol in ref) Found in cassava fermented drinks 1000 mg/kg
2-Methylpropan-2-ol None (tertiary alcohol) Identified, not quantified, in beer[5] 2743 mg/kg
2-Phenylethan-1-ol ? 0.1% in non-yeasted cider (Kieser 1964): 100 mg/100 mL 1790 mg/kg
3-Methylbutan-1-ol ? 1.5% (mean) in French Brandy: 859–2108 mg/100 mL 1300 mg/kg

Difference to ethanol

[edit]
IUPAC name % intoxication by alcoholic drink (ABV x potency compared to EtOH / total ABV) Therapeutic index (Potency compared to EtOH/EtOH LD50:LD50 ratio) Potency compared to EtOH EtOH LD50:LD50 ratio
Ethanol - - - -
Propan-1-ol 21%: 2,8×3÷40 0.8 (mean): 0.5-1.1 3 (mean): 2-4 3.8
2-(1H-Indol-3-yl)ethanol ? ? ? ?
2-Methylbutan-1-ol ? ? ? 1.7
2-methylpropan-1-ol ? ? ? ?
2-Methylbutan-2-ol 28%: 0.07×20÷5 2.8 20 7.1
2-Methylpropan-2-ol ? ? ? 2.6
2-Phenylethan-1-ol ? ? ? ?
3-Methylbutan-1-ol ? ? ? 5.4

Characteristic

[edit]
IUPAC name Color/Form[6] Odor[6] Taste[6]
Ethanol Clear, colorless, very mobile liquid Mild, rather pleasant; like wine or whiskey. Weak, ethereal, vinous odor. Burning, slightly sweet
Propan-1-ol Colorless liquid Similar to ethanol Characteristic ripe, fruity flavor. Burning taste
2-(1H-Indol-3-yl)ethanol ? ? ?
2-Methylbutan-1-ol Oily, clear liquid. Colorless liquid Characteristic, disagreeable odor. Pungent, repulsive taste
2-methylpropane-1-ol Colorless, oily liquid. Clear, colorless, refractive, mobile liquid. Suffocating odor of fusel oil. Slightly suffocating; nonresidual alcoholic. Sweet, musty odor Sweet whiskey taste
2-Methylbutan-2-ol Colorless liquid Characteristic odor. Camphor odor Burning taste
2-Methylpropan-2-ol Colorless liquid or solid (crystals) (above 78 degrees F) Camphor-like odor ?
2-Phenylethan-1-ol ? Intense odour of roses Burning
3-Methylbutan-1-ol Oily, clear liquid. Colorless liquid. Characteristic, disagreeable odor. Pungent, repulsive taste

References

[edit]
  1. ^ Aroma of Beer, Wine and Distilled Alcoholic Beverages
  2. ^ "ChemIDplus Advanced". Chem.sis.nlm.nih.gov. Retrieved 2013-02-05.
  3. ^ "Propanol, 1- (EHC 102, 1990)". Inchem.org. 1989-04-14. Retrieved 2013-02-05.
  4. ^ "2-Methyl-1-Butanol". Grrexports.com. Retrieved 2013-02-05.
  5. ^ "t-butyl alcohol". Toxnet.nlm.nih.gov. Retrieved 2013-02-05.
  6. ^ a b c Pubchem Compound, https://pubchem.ncbi.nlm.nih.gov/
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