Amfecloral

Last updated
Amfecloral
Amfecloral.png
Clinical data
Other namesalpha-methyl-N-(2,2,2-trichloroethylidene)phenethylamine;
N-(2,2,2-trichloroethylidene)amphetamine
ATC code
  • none
Legal status
Legal status
  • In general: unscheduled
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), also known as amphecloral (USAN), is a stimulant drug of the phenethylamine and amphetamine chemical classes that was used as an appetite suppressant under the trade name Acutran, but is now no longer marketed. [1] It was classified as an anorectic drug with little to no stimulant activity in a 1970 review. [2] The British Pharmacopoeia Commission approved the name in 1970. [3] The raw ingredients used in manufacturing it were d-amphetamine and chloral hydrate. [4]

Contents

Pharmacology

Amfecloral is metabolised to both d-(S)- and l-(R)-amphetamine and, most likely, also to chloral hydrate. [5] Amphetamine is a psychostimulant, whereas chloral hydrate is a sedative/hypnotic drug.

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

See also

Related Research Articles

<span class="mw-page-title-main">Amphetamine</span> Central nervous system stimulant

Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.

<span class="mw-page-title-main">Stimulant</span> Drug that increases activity of central nervous system

Stimulants are a class of drugs that increase the activity of the brain. They are used for various purposes, such as enhancing alertness, attention, motivation, cognition, mood, and physical performance. Some of the most common stimulants are caffeine, nicotine, amphetamines, cocaine, methylphenidate, and modafinil.

<span class="mw-page-title-main">Chloral hydrate</span> Chemical sedative and hypnotic drug

Chloral hydrate is a geminal diol with the formula Cl3C−CH(OH)2. It was first used as a sedative and hypnotic in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in usage in the United States until at least the 1970s. It sometimes finds usage as a laboratory chemical reagent and precursor. It is derived from chloral (trichloroacetaldehyde) by the addition of one equivalent of water.

<span class="mw-page-title-main">Dextroamphetamine</span> CNS stimulant and isomer of amphetamine

Dextroamphetamine (INN:dexamfetamine) is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used as an athletic performance and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.

Stimulant psychosis is a mental disorder characterized by psychotic symptoms. It involves and typically occurs following an overdose or several day binge on psychostimulants, though one study reported occurrences at regularly prescribed doses in approximately 0.1% of individuals within the first several weeks after starting amphetamine or methylphenidate therapy. Methamphetamine psychosis, or long-term effects of stimulant use in the brain, depend upon genetics and may persist for some time.

<span class="mw-page-title-main">Phenylpropanolamine</span> Sympathomimetic agent

Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to control urinary incontinence in dogs.

<span class="mw-page-title-main">Adderall</span> Drug mixture used mainly to treat ADHD and narcolepsy

Adderall and Mydayis are trade names for a combination drug called mixed amphetamine salts containing four salts of amphetamine. The mixture is composed of equal parts racemic amphetamine and dextroamphetamine, which produces a (3:1) ratio between dextroamphetamine and levoamphetamine, the two enantiomers of amphetamine. In terms of base, rather than salts, the ratio is 3.15:1 for dextro- to levoamphetamine. Both enantiomers are stimulants, but differ enough to give Adderall an effects profile distinct from those of racemic amphetamine or dextroamphetamine, which are marketed as Evekeo and Dexedrine/Zenzedi, respectively. MAS is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used illicitly as an athletic performance enhancer, cognitive enhancer, appetite suppressant, and recreationally as a euphoriant. It is a central nervous system (CNS) stimulant of the phenethylamine class.

<span class="mw-page-title-main">Phenylacetone</span> Chemical compound

Phenylacetone, also known as phenyl-2-propanone, is an organic compound with the chemical formula C6H5CH2COCH3. It is a colorless oil that is soluble in organic solvents. It is a mono-substituted benzene derivative, consisting of an acetone attached to a phenyl group. As such, its systematic IUPAC name is 1-phenyl-2-propanone.

<span class="mw-page-title-main">4-Hydroxyamphetamine</span> Group of stereoisomers

4-Hydroxyamphetamine (4HA), also known as hydroxyamfetamine, hydroxyamphetamine, oxamphetamine, norpholedrine, para-hydroxyamphetamine, and α-methyltyramine, is a drug that stimulates the sympathetic nervous system.

<i>alpha</i>-Pyrrolidinopropiophenone Chemical compound

α-Pyrrolidinopropiophenone (α-PPP), is a stimulant drug. It is similar in structure to the appetite suppressant diethylpropion and has analogous effects in animals. Little is known about this compound, but it has been detected by laboratories in Germany as an ingredient in "ecstasy" tablets seized by law enforcement authorities. This drug has been found to produce stimulant effects in animals and produces highly stimulating effects in humans, based on the experiences of the individuals who have tried it. Most of the individuals who have tried it prefer α-PVP to it, but prefer this drug over α-PVT. It is said to lack euphoria compared to α-PVP.

<span class="mw-page-title-main">Lisdexamfetamine</span> Central nervous system stimulant prodrug

Lisdexamfetamine, sold under the brand names Vyvanse and Elvanse among others, is a stimulant medication that is used to treat attention deficit hyperactivity disorder (ADHD) in children and adults and for moderate-to-severe binge eating disorder in adults. Lisdexamfetamine is taken by mouth. Its effects generally begin within two hours and last for up to 14 hours. In the United Kingdom, it is usually less preferred to methylphenidate for the treatment of children.

<span class="mw-page-title-main">Mefenorex</span> Pharmaceutical drug

Mefenorex is a stimulant drug which was used as an appetite suppressant. It is an amphetamine derivative which was developed in the 1970s and used for the treatment of obesity. Mefenorex produces amphetamine as a metabolite, and has been withdrawn in many countries despite having only mild stimulant effects and relatively little abuse potential.

<span class="mw-page-title-main">Levoamphetamine</span> CNS stimulant and isomer of amphetamine

Levoamphetamine is a stimulant medication which is used in the treatment of certain medical conditions. It was previously marketed by itself under the brand name Cydril, but is now available only in combination with dextroamphetamine in varying ratios under brand names like Adderall and Evekeo. The drug is known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries. Levoamphetamine is taken by mouth.

<span class="mw-page-title-main">4'-Methoxy-α-pyrrolidinopropiophenone</span> Stimulant recreational drug

4'-Methoxy-α-pyrrolidinopropiophenone (MOPPP) is a stimulant designer drug of the pyrrolidinophenone class. It has the potential to produce euphoria, an effect shared with other classical stimulants.

<span class="mw-page-title-main">Amfonelic acid</span> Chemical compound

Amfonelic acid is a research chemical and dopaminergic stimulant with antibiotic properties. Although limited clinical trials have been conducted, it's primarily used in scientific research.

<span class="mw-page-title-main">3-Methoxyamphetamine</span> Stimulant drug of the amphetamine class

meta-Methoxyamphetamine (MMA), also known as 3-methoxyamphetamine (3-MA), is a stimulant drug from the amphetamine family. It has similar effects in animal drug discrimination tests to the more widely known derivative 4-methoxyamphetamine (PMA), although with a slightly different ratio of monoamine release, being a combined serotonin, dopamine, and norepinephrine releasing agent rather than a fairly selective serotonin releaser like PMA. 3-Methoxyamphetamine has similarly appeared on the illicit market as a designer drug alternative to MDMA, although far more rarely than its infamous positional isomer. It produces gepefrine, a cardiac stimulant, as one of its major metabolites.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<span class="mw-page-title-main">4-Hydroxyphenylacetone</span> Chemical compound

4-Hydroxyphenylacetone is the para-hydroxy analog of phenylacetone, an inactive metabolite of amphetamine in humans. When it occurs as a metabolite of amphetamine, it is produced directly from the inactive metabolite phenylacetone.

<i>para</i>-Chloromethamphetamine Chemical compound

para-Chloromethamphetamine is a stimulant that is the N-methyl derivative and prodrug of the neurotoxic drug para-chloroamphetamine (4-CA). It has been found to decrease serotonin in rats. Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of serotonin and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug.

Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, crystal, crank, bennies, and speed. Within the group of amphetamine-type stimulants, there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine.

References

  1. 1 2 Ganellin CR, Triggle DJ (1996). Dictionary of pharmacological agents, Volumes 1-2. Chapman & Hall. p. 67. ISBN   9780412466304.
  2. 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.
  3. "Notes and News". The Lancet. 296 (7675): 730–732. October 1970. doi:10.1016/S0140-6736(70)92010-6.
  4. McPherson EM (2007). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 244. ISBN   9780815518563.
  5. "NCATS Inxight Drugs — AMFECLORAL, (+)-". drugs.ncats.io. Retrieved 2024-07-16.