Comparison of psychoactive alcohols in alcoholic drinks

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

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	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

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

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

1. Aroma of Beer, Wine and Distilled Alcoholic Beverages
2. "ChemIDplus Advanced". Chem.sis.nlm.nih.gov. Archived from the original on August 15, 2000. 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. Pubchem Compound, https://pubchem.ncbi.nlm.nih.gov/