Methylpentynol

Methylpentynol

Clinical data
Trade names	Oblivon
Routes of administration	By mouth
ATC code	N05CM15 (WHO)
Legal status
Legal status	Withdrawn
Identifiers
IUPAC name 3-methylpent-1-yn-3-ol
CAS Number	77-75-8 Y
PubChem CID	6494
ChemSpider	21106516 N
UNII	B017BC5B1N
CompTox Dashboard (EPA)	DTXSID5021756
ECHA InfoCard	100.000.960
Chemical and physical data
Formula	C6H10O
Molar mass	98.145 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(C)(C#C)O
InChI InChI=1S/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3 N Key:QXLPXWSKPNOQLE-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Methylpentynol (Methylparafynol, Dormison, Atemorin, Oblivon) is a tertiary hexynol with hypnotic/sedative and anticonvulsant effects and an exceptionally low therapeutic index. It was discovered by Bayer in 1913 and was used shortly thereafter for the treatment of insomnia, but its use was quickly phased out in response to newer drugs with far more favorable safety profiles.

The drug was marketed again in the United States, Europe and elsewhere from 1956 well into the 1960s as a rapid-acting sedative. The drug was quickly overshadowed at that point by benzodiazepines and is no longer sold anywhere.

Synthesis

Methylpentynol is prepared by reaction of butanone (MEK) with sodium acetylide. This reaction must be done in anhydrous conditions and in an inert atmosphere.

Applications

As building block in the synthesis of:

1. Phthalofyne (1,2-Benzenedicarboxylic acid, mono(1-ethyl-1-methyl-2-propynyl) ester) [131-67-9]
2. Anansiol (1-ethyl-1-methylprop-2-ynyl carbamate) [302-66-9]
3. Bason ( 2-Bromoethynyl-2-butanol) [2028-52-6]

See also

• Clocental
• Ethchlorvynol