Bemegride

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Bemegride
Clinical data
Trade names	Mikedimide (Panray), Eukraton (Nordmark), Malysol (Arco, Switzerland), Megimide (Nicholas)
Synonyms	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 ;
PubChem CID	2310;
ChemSpider	2220 ;
UNII	57DQA39DO2;
KEGG	D01957 ;
ChEMBL	ChEMBL1214192 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C8H13NO2
Molar mass	155.194 g/mol
3D model (JSmol)	Interactive image;
Melting point	127 °C (260.6 °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) ; Key:ORRZGUBHBVWWOP-UHFFFAOYSA-N ;
(verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Bemegride (also marketed as Megimide) is a central nervous system stimulant and antidote for barbiturate poisoning^[1] as its chemoreceptor agonism increases mean tidal volume, thereby increasing respiration and the concentration of O₂ in blood although it may be theoretically used as a supportive measure in treating any depressant overdose. The drug's synthesis was invented in 1911.^[2]

John Bodkin Adams case

Bemegride is notable in legal history as the drug suspected serial killer Dr John Bodkin Adams 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.^[3]

Animal use

Bemegride is also used to induce convulsions in experimental animals.^[4]

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 bemigride 7.

References

↑ Hofmeister, Alfred (2000). "Analeptics". Ullmann's Encyclopedia of Industrial Chemistry: 1–2. doi:10.1002/14356007.a02_267.
↑ ^2.0 ^2.1 Thole, Ferdinand Bernard; Thorpe, Jocelyn Field (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.
↑ Cullen, Pamela V., A Stranger in Blood: The Case Files on Dr John Bodkin Adams, London, Elliott & Thompson, 2006, ISBN 1-904027-19-9
↑ Definition: bemegride from Online Medical Dictionary

[1] Hofmeister, Alfred (2000). "Analeptics". Ullmann's Encyclopedia of Industrial Chemistry: 1–2. doi:10.1002/14356007.a02_267.

[Thole-2] 2.0 ^2.1 Thole, Ferdinand Bernard; Thorpe, Jocelyn Field (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] Cullen, Pamela V., A Stranger in Blood: The Case Files on Dr John Bodkin Adams, London, Elliott & Thompson, 2006, ISBN 1-904027-19-9

[4] Definition: bemegride from Online Medical Dictionary

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