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 It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side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.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[1]

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)^[1] 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)

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Meprobamate

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