UserWiki:David Hedlund/Comparison of psychoactive alcohols in alcoholic drinks - PsychonautWiki

UserWiki:David Hedlund/Comparison of psychoactive alcohols in alcoholic drinks

Contrary to popular belief, fermented alcoholic drinks usually contain several alcohols, but in smaller amounts than ethanol, that act as psychoactive drugs with different degrees of potency and effects and also contribute to the color, odor, and flavor of beverages.

Alcohol is a highly diverse chemical class of organic compounds that contain one or more hydroxyl (-OH) functional groups bound to a carbon atom. Alcohols are classified into primary, secondary (sec-, s-), and tertiary (tert-, t-) alcohols, based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl functional group.

General

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

IUPAC name Toxic metabolite(s) Alcohol by volume (ABV)[1] LD50 in rat, oral[2]
Ethanol 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 7070 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) 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

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 ? ? ? 1.0
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

IUPAC name Color/Form[5] Odor[5] Taste[5]
Ethanol Clear, colorless, very mobile liquid Mild, rather pleasant; like wine or whiskey. Weak, ethereal, vinous odor. Burning
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

  1. ↑ Aroma of Beer, Wine and Distilled Alcoholic Beverages
  2. ↑ "ChemIDplus Advanced - Chemical information with searchable synonyms, structures, and formulas". chem.nlm.nih.gov. 
  3. ↑ "Propanol, 1- (EHC 102, 1990)". Inchem.org. 1989-04-14. Retrieved 2013-02-05. 
  4. ↑ "2-methylbutan-1-ol". www.chembk.com. 
  5. ↑ 5.0 5.1 5.2 Pubchem Compound, https://pubchem.ncbi.nlm.nih.gov/
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