Meprobamate

Meprobamate
Clinical data
Trade names	Miltown, Equanil, Meprospan, Amepromat, Quivet, Zirponand, and many others
AHFS/Drugs.com	Monograph
MedlinePlus	a682077
Pregnancy; category	AU: C;
Routes of; administration	Oral
ATC code	N05BC01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class C; US: Schedule IV;
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	10 hours
Excretion	Renal
Identifiers
	IUPAC name [2-(carbamoyloxymethyl)-2-methyl-pentyl] carbamate;
CAS Number	57-53-4 ;
PubChem CID	4064;
IUPHAR/BPS	7225;
DrugBank	DB00371 ;
ChemSpider	3924 ;
UNII	9I7LNY769Q;
KEGG	D00376 ;
ChEMBL	ChEMBL979 ;
CompTox Dashboard (EPA)	DTXSID3023261 ;
ECHA InfoCard	100.000.306
Chemical and physical data
Formula	C9H18N2O4
Molar mass	218.253 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.229 g/cm3
Melting point	105 to 106 °C (221 to 223 °F)
Boiling point	200 °C (392 °F) to 210 °C (410 °F)
	SMILES O=C(N)OCC(C)(CCC)COC(N)=O;
	InChI InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13) ; Key:NPPQSCRMBWNHMW-UHFFFAOYSA-N ;
	(verify)

Meprobamate—marketed as Miltown by Wallace Laboratories and Equanil by Wyeth, among others—is a carbamate derivative used as an anxiolytic drug. It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side effects.

Clinical data


Trade names	Miltown, Equanil, Meprospan, Amepromat, Quivet, Zirponand, and many others
AHFS/Drugs.com	Monograph
MedlinePlus	a682077
Pregnancy category	AU: C
Routes of administration	Oral
ATC code	N05BC01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class B1 (Psychoactive drugs) CA: Schedule IV DE: Anlage II (Authorized trade only, not prescriptible) UK: Class C US: Schedule IV
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	10 hours
Excretion	Renal
Identifiers
IUPAC name [2-(carbamoyloxymethyl)-2-methyl-pentyl] carbamate
CAS Number	57-53-4^Y
PubChem CID	4064
IUPHAR/BPS	7225
DrugBank	DB00371^Y
ChemSpider	3924^Y
UNII	9I7LNY769Q
KEGG	D00376^Y
ChEMBL	ChEMBL979^Y
CompTox Dashboard (EPA)	DTXSID3023261
ECHA InfoCard	100.000.306
Chemical and physical data
Formula	C₉H₁₈N₂O₄
Molar mass	218.253 g·mol⁻¹
3D model (JSmol)	Interactive image
Density	1.229 g/cm³
Melting point	105 to 106 °C (221 to 223 °F)
Boiling point	200 °C (392 °F) to 210 °C (410 °F)
SMILES O=C(N)OCC(C)(CCC)COC(N)=O
InChI InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)^Y Key:NPPQSCRMBWNHMW-UHFFFAOYSA-N^Y
(verify)