Amfecloral

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Amfecloral
Amfecloral.png
Clinical data
Trade names Acutran
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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H12Cl3N
Molar mass 264.57 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+ Yes check.svgY
  • Key:VBZDETYCYXPOAK-OVCLIPMQSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Amfecloral (INN) or amphecloral (USAN) is a combination drug pairing a Central Nervous System (CNS) stimulant, specifically dextroamphetamine, with a sedative-hypnotic depressant, specifically chloral hydrate.

Contents

Widely used in the 1900s for its anorectic (appetite-suppressing) effects, amfecloral was approved by the United States Food and Drug Administration for treatment of obesity, marketed and distributed under the brand name Acutran, until production and marketing ceased in 1973, concurrent with similar combination anorectics, Desbutal (methamphetamine-pentobarbital) and Obetrol (methamphetamine-dextroamphetamine).

Naming and Classification

The British Pharmacopoeia Commission approved the name in 1970. [2] and therefore a de facto combination drug similar to other such anti-obesity drugs in use at the time, such as Desbutal, Dexamyl, and Obetrol. Amfecloral belongs to the phenethylamine and substituted amphetamine chemical classes.

Synthesis and Pharmacology

The raw ingredients used in manufacturing it were dextroamphetamine and chloral hydrate. [3]

Upon ingestion and metabolization, amfecloral is metabolized as dextroamphetamine and chloral hydrate, as well as converting into levoamphetamine, the R enantiomer of amphetamine. [4] Amphetamine is a stimulant, whereas chloral hydrate is a sedative/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.

History

Combination Drugs in the Twentieth Century

Acutran was one of several brands, amfecloral one of several formulations distributed as anorectic combination drugs comprising a CNS stimulant and a CNS depressant –respectively known as "uppers" and "downers" in common parlance, conjoined in the form of one pill: others included Desbutal (methamphetamine-pentobarbital) and Obetrol (meth-dexamphetamine), both of which were discontinued concurrent to Acutran in 1973; [Eskatrol]] (amphetamine and the neuroleptic compazine, discontinued 1981), in addition to Dexamyl (dextamphetamine-amylbarbitone). [1]

Efficacy and Tolerability

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

Following increased scrutiny of combination medications comprising psychostimulant and sedative components with the 1962 passage of the Kefauver-Harris Amendment, then the Controlled Substances Act of 1970, Acutran was withdrawn from the U.S. pharmaceutical market and ceased production, alongside Desbutal (methamphetamine-pentobarbital) and Obetrol (methamphetamine-dextroamphetamine), all three of which were fully discontinued by the end of 1973.

See also

References

  1. 1 2 Ganellin 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. Retrieved 2024-07-16.
  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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