U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C10H20N2O4
Molecular Weight 232.2768
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEBUTAMATE

SMILES

CCC(C)C(C)(COC(N)=O)COC(N)=O

InChI

InChIKey=LEROTMJVBFSIMP-UHFFFAOYSA-N
InChI=1S/C10H20N2O4/c1-4-7(2)10(3,5-15-8(11)13)6-16-9(12)14/h7H,4-6H2,1-3H3,(H2,11,13)(H2,12,14)

HIDE SMILES / InChI

Molecular Formula C10H20N2O4
Molecular Weight 232.2768
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Mebutamate

Mebutamate (Capla, Dormate) is a biscarbamate drug that has anxiolytic, sedative, and antihypertensive effects. It is marketed under many trade names, including Capla and Dormate. Its preparation was reported in a 1959 US patent to Carter Products. It is less well known that mebutamate is also hypnotic. In a 1967 study, L. Tetreault, P. Richer, and J. M. Bordeleau in Montreal found that, at a dose of 600 mg, mebutamate has hypnotic properties that “affect the duration and quality of sleep induction, and the duration and quality of sleep, without disturbing the state of the subject upon awakening and during the morning.” A higher dose (900 mg) did not change the overall effect, which was “consistently between that of secobarbital at 200 mg and 100 mg.” The authors did not observe any significant side effects. Mebutamate is one of many GABAergic drugs which act via allosteric agonism of the GABAA receptor at the β-subreceptor similar to barbiturates. In contrast, benzodiazepines act at the α-subreceptor. As such, carbamates and barbiturates, possess analgesic properties which the benzodiazepine class of drugs does not.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DORMATE

Approved Use

Mebutamate
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:07:47 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:47 GMT 2023
Record UNII
5H8F175RER
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEBUTAMATE
INN   JAN   MART.   MI   ORANGE BOOK   USAN   WHO-DD  
USAN   INN  
Official Name English
BUTATENSIN
Brand Name English
NO-PRESS
Brand Name English
MEBUTAMATE [MART.]
Common Name English
ENCAPLA
Brand Name English
CAPLA
Brand Name English
IPOTENSIVO
Brand Name English
SIGMAFON
Brand Name English
mebutamate [INN]
Common Name English
DORMATE
Brand Name English
MEBUTAMATE, (±)-
Common Name English
W-583
Code English
1,3-PROPANEDIOL, 2-METHYL-2-(1-METHYLPROPYL)-, 1,3-DICARBAMATE
Systematic Name English
MEBUTAMAT
Common Name English
DICAMOYLMETHANE
Common Name English
NSC-163921
Code English
MEBUTAMATE [USAN]
Common Name English
2-sec-Butyl-2-methyl-1,3-propanediol dicarbamate
Systematic Name English
Mebutamate [WHO-DD]
Common Name English
CARBUTEN
Brand Name English
AXITEN
Brand Name English
MEBUTAMATE [JAN]
Common Name English
(±)-MEBUTAMATE
Common Name English
2,2-DICARBAMYLOXYMETHYL-3-METHYLPENTANE
Systematic Name English
PREAN
Brand Name English
MEBUTAMATE [ORANGE BOOK]
Common Name English
1,3-PROPANEDIOL, 2-METHYL-2-(1-METHYLPROPYL)-, DICARBAMATE
Systematic Name English
MEGA
Brand Name English
PREMINEX
Brand Name English
VALLENE
Brand Name English
MEBUTINA
Brand Name English
MIOARTRINA
Brand Name English
MEBUTAMATE [MI]
Common Name English
Classification Tree Code System Code
DEA NO. 2800
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
WHO-VATC QN05BC04
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
WHO-ATC N05BC04
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
Code System Code Type Description
NSC
163921
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200922
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
PUBCHEM
6151
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
DRUG BANK
DB06797
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
SMS_ID
100000081753
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
FDA UNII
5H8F175RER
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
DRUG CENTRAL
1644
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
NCI_THESAURUS
C66062
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
EVMPD
SUB08668MIG
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
INN
1224
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID1023239
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
MERCK INDEX
m7112
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-587-5
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
WIKIPEDIA
MEBUTAMATE
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
CAS
64-55-1
Created by admin on Fri Dec 15 15:07:47 GMT 2023 , Edited by admin on Fri Dec 15 15:07:47 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY