Oenethyl

Last updated

Oenethyl
Oenethyl.svg
Clinical data
Trade names Pacamine; Neosupranol
Other namesŒnethyl; Önethyl; 2-Methylaminoheptane; N,1-Dimethylhexylamine; 2-Heptylmethylamine; 2-(N-Methyl)heptylamine
Drug class Sympathomimetic; Vasopressor; Nasal decongestant
Identifiers
  • N-methylheptan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C8H19N
Molar mass 129.247 g·mol−1
3D model (JSmol)
  • CCCCCC(C)NC
  • InChI=1S/C8H19N/c1-4-5-6-7-8(2)9-3/h8-9H,4-7H2,1-3H3
  • Key:BGWFQRDYRSCOCO-UHFFFAOYSA-N

Oenethyl, also known as 2-methylaminoheptane and sold under the brand names Pacamine and Neosupranol, is a sympathomimetic and vasopressor medication of the alkylamine which is no longer marketed. [1] [2] [3] It was used as a nasal decongestant and to control blood pressure during anesthesia. [3] It is closely structurally related to other alkylamines, for instance methylhexanamine and tuaminoheptane, among others. [3] These compounds are known to act as structurally simple monoamine releasing agents and to produce psychostimulant-like effects. [4] [5] [6] [2]

See also

Related Research Articles

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

Pseudoephedrine, sold under the brand name Sudafed among others, is a sympathomimetic medication which is used as a decongestant to treat nasal congestion. It has also been used off-label for certain other indications, like treatment of low blood pressure. At higher doses, it may produce various additional effects including stimulant, appetite suppressant, and performance-enhancing effects. In relation to this, non-medical use of pseudoephedrine has been encountered. The medication is taken by mouth.

<span class="mw-page-title-main">Ephedrine</span> Medication and stimulant

Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection, it lasts about an hour, and when taken by mouth, it can last up to four hours.

A decongestant, or nasal decongestant, is a type of pharmaceutical drug that is used to relieve nasal congestion in the upper respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine. Intranasal corticosteroids can also be used as decongestants and antihistamines can be used to alleviate runny nose, nasal itch, and sneezing.

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

Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was previously commonly used in prescription and over-the-counter cough and cold preparations. The medication is taken by mouth.

<span class="mw-page-title-main">Propylhexedrine</span> Topical nasal decongestant

Propylhexedrine, sold under the brand name Benzedrex among others, is an alkylamine primarily utilized as a topical nasal decongestant. Its main indications are relief of congestion due to colds, allergies, and allergic rhinitis. Propylhexedrine was first used medically in 1949, with the release of Benzedrex by Smith, Kline & French, and it has been used, mainly within the United States, since then.

<span class="mw-page-title-main">Sympathomimetic drug</span> Substance that mimics effects of catecholamines

Sympathomimetic drugs are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in heart rate, force of cardiac contraction, and blood pressure. The primary endogenous agonists of the sympathetic nervous system are the catecholamines, which function as both neurotransmitters and hormones. Sympathomimetic drugs are used to treat cardiac arrest and low blood pressure, or even delay premature labor, among other things.

<span class="mw-page-title-main">Phenylephrine</span> Decongestant medication

Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among others, is a medication used as a decongestant for uncomplicated nasal congestion in the form of a nasal spray or oral tablet, to dilate the pupil, to increase blood pressure given intravenously in cases of low blood pressure, and to relieve hemorrhoids as a suppository. It can also be applied to the skin.

<span class="mw-page-title-main">Levmetamfetamine</span> Topical nasal decongestant

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<span class="mw-page-title-main">Isometheptene</span> Sympathomimetic amine

Isometheptene is a sympathomimetic amine sometimes used in the treatment of migraines and tension headaches due to its vasoconstricting properties; that is, it causes constriction (narrowing) of blood vessels. Along with paracetamol and dichloralphenazone, it is one of the constituents of Amidrine.

<span class="mw-page-title-main">Cyclopentamine</span> Decongestant and stimulant drug

Cyclopentamine is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was indicated in the past as an over-the-counter (OTC) medication for use as a nasal decongestant, notably in Europe and Australia, but has now been largely discontinued.

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

Tuaminoheptane is a sympathomimetic agent and vasoconstrictor which was formerly used as a nasal decongestant. It is still used in France as a nasal decongestant but its use is not recommended by the health authorities due to the lack of evidence of its effectiveness. It has also been used as a stimulant.

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

Methylhexanamine is an indirect sympathomimetic drug invented and developed by Eli Lilly and Company and marketed as an inhaled nasal decongestant from 1948 until it was voluntarily withdrawn from the market in the 1980s.

<span class="mw-page-title-main">Phenpromethamine</span> Sympathomimetic nasal decongestant (Phenethylamine group)

Phenpromethamine, also known as N,β-dimethylphenethylamine, is a sympathomimetic nasal decongestant of the phenethylamine group. It was previously marketed as a nasal inhaler from 1943 through 1960 but is no longer available. The medication is a stimulant and is banned by the World Anti-Doping Agency. It has been detected in dietary supplements starting in the 2010s.

<span class="mw-page-title-main">Octodrine</span> DMAA substitute

Octodrine, also known as dimethylhexylamine (DMHA) and sold under the brand name Vaporpac among others, is a sympathomimetic and stimulant medication that was formerly used in the treatment of hypotension.

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

Iproheptine, also known as N-isopropyl-1,5-dimethylhexylamine or N-isopropyloctodrine and sold under the brand names Metron and Susat, is a nasal decongestant which has been marketed in Japan. It is described as a vasoconstrictor and antihistamine. The drug is available over-the-counter in Japan.

<span class="mw-page-title-main">Norepinephrine releasing agent</span> Catecholaminergic type of drug

A norepinephrine releasing agent (NRA), also known as an adrenergic releasing agent, is a catecholaminergic type of drug that induces the release of norepinephrine (noradrenaline) and epinephrine (adrenaline) from the pre-synaptic neuron into the synapse. This in turn leads to increased extracellular concentrations of norepinephrine and epinephrine therefore an increase in adrenergic neurotransmission.

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

Methylephedrine, sold under the brand name Metheph among others, is a sympathomimetic medication described as an antiasthmatic agent and used to treat coughing and nasal congestion. It is reported to be used in various over-the-counter cough and cold preparations throughout the world, including Japan.

<span class="mw-page-title-main">1,3-Dimethylbutylamine</span> Chemical compound

1,3-Dimethylbutylamine, is a stimulant drug structurally related to methylhexanamine where a butyl group replaces the pentyl group. The compound is an aliphatic amine.

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

Deterenol is a stimulant drug which acts as a beta agonist. It has been found as an ingredient of dietary supplement products, but is banned in most countries due to risk of cardiac arrest.

<span class="mw-page-title-main">Substituted β-hydroxyamphetamine</span> Class of compounds based upon the β-hydroxyamphetamine structure

Substituted β-hydroxyamphetamines, or simply β-hydroxyamphetamines, also known as phenylisopropanolamines, phenylpropanolamines, norephedrines, or cathinols, are derivatives of β-hydroxyamphetamine with one or more chemical substituents. They are substituted phenethylamines, phenylethanolamines (β-hydroxyphenethylamines), and amphetamines (α-methylphenethylamines), and are closely related to but distinct from the substituted cathinones (β-ketoamphetamines). Examples of β-hydroxyamphetamines include the β-hydroxyamphetamine stereoisomers phenylpropanolamine and cathine and the stereospecific N-methylated β-hydroxyamphetamine derivatives ephedrine and pseudoephedrine, among many others.

References

  1. Negwer M (1978). Organic-chemical Drugs and Their Synonyms: An International Survey. Organic-chemical Drugs and Their Synonyms: An International Survey. Akademie-Verlag. p. 163. ISBN   978-0-89573-100-5 . Retrieved 12 January 2025.
  2. 1 2 Rasmussen N, Keizers PH (2016). "History full circle: 'Novel' sympathomimetics in supplements". Drug Test Anal. 8 (3–4): 283–286. doi:10.1002/dta.1852. PMID   27072841. With the recent discoveries of N,α-DEPEA, NNDMPPA, methylsynephrine, BMPEA, DMAA, and DMBA as new dietary supplement ingredients the question arises: which stimulant will be next? There are a number of pressor amines that may be selected, such as the pharmaceuticals oenethyl (8) and propylhexedrine (4). In addition, many more variants that can be easily synthesized using the basic structure of the compounds illustrated in Figure 1. [...] Figure 1. Molecular structures of the compounds discussed. [...]
  3. 1 2 3 Venhuis BJ, de Kaste D (2012). "Scientific Opinion on the Regulatory Status of 1,3-Dimethylamylamine (DMAA)" (PDF). European Journal of Food Research & Review. 2 (4): 93–100. Fig. 1. Molecular structures of aliphatic amines that were used in medicines. [...] Oenethy (Bilhuber) [...] At least 5 different aliphatic amines were eventually marketed as an active ingredient of a medicine: DMAA, tuaminoheptane, octin, oenethyl and propylhexedrine (Table 3) [11]. [...] Table 3. Aliphatic amines with properties similar to DMAA [...] Oenethyl: Initially marketed as a nasal decongestant and also used to control blood pressure during anesthesia [21,22].
  4. Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, et al. (August 2023). "The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization". J Pharmacol Exp Ther. 386 (2): 266–273. doi:10.1124/jpet.122.001573. PMC   10353075 . PMID   37348963.
  5. Docherty JR, Alsufyani HA (August 2021). "Pharmacology of Drugs Used as Stimulants". J Clin Pharmacol. 61 Suppl 2: S53 –S69. doi: 10.1002/jcph.1918 . PMID   34396557.
  6. Alsufyani HA, Docherty JR (January 2019). "Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat". Eur J Pharmacol. 843: 121–125. doi:10.1016/j.ejphar.2018.10.047. PMID   30395850.