Methylpentynol

Structural formula
	Structural formula without stereochemistry
General
Non-proprietary name	Methylpentynol
other names	Methylpentinol; (±) -3-methyl-1-pentyn-3-ol; ( RS ) -3-methyl-1-pentyn-3-ol; (±) -3-methylpent-1-yn-3-ol ( IUPAC ); Meparfynol;
Molecular formula	C 6 H 10 O
Brief description	colorless, odorless, burning-tasting liquid
External identifiers / databases
EC number	201-055-5
ECHA InfoCard	100,000,960
PubChem	6494
Wikidata	Q412090
Drug information
ATC code	N05 CM15
Drug class	Sedative , hypnotic
properties
Molar mass	98.15 g · mol -1
density	0.87 g cm −3
Melting point	−30 ° C
boiling point	121 ° C
Vapor pressure	7 h Pa (20 ° C)
solubility	easily in water (112 g l −1 at 20 ° C)
Refractive index	1.431
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 226-302-318-412
	P: ?
Toxicological data	525 mg kg −1 ( LD 50 , mouse , oral ) ; 537 mg kg −1 ( LD 50 , rat , ip ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Methylpentynol ( INN ), also methylpentinol or meparfynol , is a drug from the group of sedatives and hypnotics . Chemically, it is a combination of alkynes and alcohols that was patented by Bayer in 1913 .

The carbamate of methylpentynol was used as an active ingredient in sleeping pills and sedatives. Due to the development of substances with a more favorable action and safety profile, methylpentynol no longer has any therapeutic significance. In Germany, Austria and Switzerland there are no longer any preparations on the market.

Properties and safety information

Methylpentynol is a colorless, odorless, highly flammable liquid that dissolves easily in water. The mixtures of methylpentynol vapor with air are explosive in the range between 1.8 and 16% by volume. The substance is hazardous to water. In animal experiments with mice and rats, methylpentynol showed symptoms such as drowsiness, muscle twitching and reduced height gain, despite relatively high LD ₅₀ values, even at lower doses.

use

By reaction with 2-butanone in liquid ammonia and in the presence of potassium hydroxide may be 3,6-dimethyl-4-octyne-3,6-diol are obtained.

Individual evidence

↑ Entry on methylpentynol. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 3-methyl-1-pentyn-3-ol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ Data sheet 3-Methyl-1-pentyn-3-ol from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
^ ^A ^b Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963 .
^ ^A ^b British Journal of Pharmacology and Chemotherapy . Vol. 11, Pg. 20, 1956 .
↑ Google Patents: EP1808426A1 - Process for the preparation of alkynediols - Google Patents , accessed December 4, 2018.

[Römpp-1] Entry on methylpentynol. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 3-methyl-1-pentyn-3-ol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[3] Data sheet 3-Methyl-1-pentyn-3-ol from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).

[ppsc-4] A ^b Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963 .

[bjpc-5] A ^b British Journal of Pharmacology and Chemotherapy . Vol. 11, Pg. 20, 1956 .

[google.com-6] Google Patents: EP1808426A1 - Process for the preparation of alkynediols - Google Patents , accessed December 4, 2018.