Bemegride

Bemegride

Clinical data
Trade names	Megimide, others
Other names	Methetharimide β,β-methylethylglutarimide
AHFS/Drugs.com	International Drug Names
ATC code	R07AB05 ( WHO )
Legal status
Legal status	AU: S4 (Prescription only)
Identifiers
IUPAC name 4-ethyl-4-methylpiperidine-2,6-dione
CAS Number	64-65-3  Y
PubChem CID	2310
ChemSpider	2220  Y
UNII	57DQA39DO2
KEGG	D01957  Y
ChEMBL	ChEMBL1214192  Y
CompTox Dashboard (EPA)	DTXSID0045250
ECHA InfoCard	100.000.535
Chemical and physical data
Formula	C8H13NO2
Molar mass	155.197 g·mol−1
3D model (JSmol)	Interactive image
Melting point	127 °C (261 °F)
SMILES O=C1NC(=O)CC(CC)(C1)C
InChI InChI=1S/C8H13NO2/c1-3-8(2)4-6(10)9-7(11)5-8/h3-5H2,1-2H3,(H,9,10,11) Y Key:ORRZGUBHBVWWOP-UHFFFAOYSA-N Y
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Bemegride, sold under the brand name Megimide among others, is a central nervous system (CNS) stimulant ^[1] first manufactured in 1911, ^[2] and which has been used in hypnotic overdose. ^[1]

As with other chemoreceptor agonists, it is a potent emetic at doses above those normally used in management of barbiturate overdose, although vomiting and aspiration are a concern during treatment. It is a controlled substance in some countries. ^[1] , and is sometimes used to induce convulsions in experimental animals. ^[3]

Synthesis

Bemegride synthesis:

The original synthesis involves first the condensation of methylethylketone with two equivalents of cyanoacetamide. The product can be rationalized by assuming first aldol condensation of ketone and active methylene compound followed by dehydration to give 3. Conjugate addition of a second molecule of cyanoacetamide would afford 4. Addition of one of the amide amines to the nitrile would then afford the iminonitrile 5. The observed product 6 can be rationalized by assuming loss of the carboxamide under strongly basic conditions. Decarboxylative hydrolysis of 6 then leads to bemegride 7.

Society and culture

John Bodkin Adams case

Further information: John Bodkin Adams § Gertrude Hullett

Bemegride was the drug which suspected serial killer John Bodkin Adams who, as a general practitioner, failed to prescribe correctly to his patient Gertrude Hullett. Hullett took an overdose of barbiturates on 19 July 1956, but Adams only gave her a single 10cc dose of bemegride three days later on the 22nd, despite having acquired 100cc for her treatment. Hullett died the next day on 23 July 1956. Adams was charged but never tried for her murder. ^[4]

References

1. Hofmeister A (2000). "Analeptics". Ullmann's Encyclopedia of Industrial Chemistry: 1–2. doi:10.1002/14356007.a02_267. ISBN   3527306730.
2. Thole FB, Thorpe JF (1911). "LIII.—The formation and reactions of iminocompounds. Part XV. The production of imino-derivatives of piperidine leading to the formation of the ββ-disubstituted glutaric acids". Journal of the Chemical Society, Transactions. 99: 422–448. doi:10.1039/CT9119900422.
3. Definition: bemegride from Online Medical Dictionary
4. Cullen, Pamela V., A Stranger in Blood: The Case Files on Dr John Bodkin Adams, London, Elliott & Thompson, 2006, ISBN   1-904027-19-9