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Amfecloral

From Wikipedia, the free encyclopedia
Withdrawn appetite suppressant drug

Pharmaceutical compound
Amfecloral
Clinical data
Trade namesAcutran
Other namesalpha-methyl-N-(2,2,2-trichloroethylidene)phenethylamine;
N-(2,2,2-trichloroethylidene)amphetamine
Drug class
ATC code
  • none
Legal status
Legal status
  • ?
Identifiers
  • 2,2,2-trichloro-N-(1-phenylpropan-2-yl)ethanimine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H12Cl3N
Molar mass264.57 g·mol−1
3D model (JSmol)
  • ClC(Cl)(Cl)/C=N/C(Cc1ccccc1)C
  • InChI=1S/C11H12Cl3N/c1-9(15-8-11(12,13)14)7-10-5-3-2-4-6-10/h2-6,8-9H,7H2,1H3/b15-8+ checkY
  • Key:VBZDETYCYXPOAK-OVCLIPMQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Amfecloral (INN) oramphecloral (USAN) is acombination drug containing acentral nervous system (CNS)stimulant andanorectic drug,dextroamphetamine, as well as aCNS depressant andsedative-hypnotic,chloral hydrate.

Widely used for itsanorectic properties, amfecloral was approved by theUnited StatesFood and Drug Administration as ananti-obesity drug andmarketed and distributed under thebrand nameAcutran. Upon 1962 passage of theKefauver-Harris Amendment, pressure grew to withdraw the product from the market, and in 1973, production ceased for Acutran and its generic formulation, concurrent with similar combination anorectics,Desbutal (methamphetamine-pentobarbital) andObetrol (methamphetamine-dextroamphetamine).

Naming and Classification

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The British Pharmacopoeia Commission approved the nameamfecloral in 1970.[2] It is classified as acombination drug constituting active ingredients belong to thephenethylamine andethanolchemical classes, similar to many combination drugs in widespread use at the time for various indications, includingDesbutal,Dexamyl (also brandedAmoDex), andObetrol.Amfecloral belongs to thephenethylamine andsubstituted amphetaminechemical classes.

Synthesis and Pharmacology

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The raw ingredients used in manufacturing it weredextroamphetamine andchloral hydrate.[3]

Upon ingestion and metabolization, amfecloral is metabolized as dextroamphetamine andchloral hydrate, as well as converting intolevoamphetamine, the Renantiomer ofamphetamine.[4] Amphetamine is astimulant, whereas chloral hydrate is asedative/hypnotic drug.[5]

The extent of metabolism and in-vivo contribution of a chloral hydrate metabolism to its purported "little to no stimulant activity" is unknown.[citation needed]

History

[edit]

Combination Drugs in the Twentieth Century

[edit]

Acutran was one of several brands, amfecloral one of several formulations distributed asanorecticcombination drugs comprising a CNSstimulant and a CNSdepressant–respectively known as "uppers" and "downers"in common parlance, conjoined in the form of one pill: others includedDesbutal (methamphetamine-pentobarbital) and Obetrol (meth-dexamphetamine), both of which were discontinued concurrent to Acutran in 1973;Eskatrol (amphetamine and theneurolepticcompazine, discontinued 1981), in addition toDexamyl (dextamphetamine-amylbarbitone).[1]

Efficacy and Tolerability

[edit]

A review from 1970 specified that amfecloral was unique among amphetamine-like substances in that it displayed little to no stimulant activity, likely due to the powerful sedating effects of chloral hydrate, the same claims were not made of the other combination medications.[6]

The extent of metabolism and in-vivo contribution of a chloral hydrate metabolism to its purported "little to no stimulant activity" is unknown.[citation needed]

Discontinuation

[edit]

Following increased scrutiny of combination medications comprisingpsychostimulant andsedative components with the 1962 passage of theKefauver-Harris Amendment, then theControlled Substances Act of 1970, Acutran was withdrawn from the U.S. pharmaceutical market and ceased production, alongsideDesbutal (methamphetamine-pentobarbital) andObetrol (methamphetamine-dextroamphetamine), all three of which were fully discontinued by the end of 1973.

See also

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References

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  1. ^abGanellin CR, Triggle DJ (1996).Dictionary of pharmacological agents, Volumes 1-2. Chapman & Hall. p. 67.ISBN 9780412466304.
  2. ^"Notes and News".The Lancet.296 (7675):730–732. October 1970.doi:10.1016/S0140-6736(70)92010-6.
  3. ^McPherson EM (2007).Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 244.ISBN 9780815518563.
  4. ^"NCATS Inxight Drugs — AMFECLORAL, (+)-".drugs.ncats.io. Retrieved2024-07-16.
  5. ^Pagel JF, Parnes BL (June 2001)."Medications for the Treatment of Sleep Disorders: An Overview".Primary Care Companion to the Journal of Clinical Psychiatry.3 (3):118–125.doi:10.4088/pcc.v03n0303.PMC 181172.PMID 15014609.
  6. ^Van Rossum JM (1970). "Mode of action of psychomotor stimulant drugs".International Review of Neurobiology.12:307–83.doi:10.1016/s0074-7742(08)60065-3.ISBN 9780123668127.PMID 4918147.
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